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With amazing water views (some of best on Cape) this wonderfully comfortable house is lovingly furnished (Persian rugs, antiques, authentic cottage furniture, custom made coaches, chairs, day bed,and stuffed rocking chairs) and as such has a unique ambiance. Unlike the typically constructed house, Windward is a post and beam structure (all wood inside and out) that is also an incredibly bright/light home. In addition the homeowners wanted a house that was a quintessential cape cod house from the street side view but wanted much glass on the water side of the house to to take advantage of the amazing views. It has an open floor plan (but also with niches and crannies), 15 ft. cathedral ceilings and enormous numbers of 6 ft by 6 ft windows showcase the amazing panoramic water views and spectacular sunsets. The living area is essentially a huge screened porch (if the gliders are open and the A/C off).
This house provides it all. Windward offers you a ''turnkey'' home to start your summer vacation. You need only bring yourself and your own personal items as Windward is totally set up for you to start your vacation from the moment you arrive. No making beds,lugging beach gear,or anything else for that matter. Only SHED LESS dogs are permitted unless specifically agreed between homeowner and vacationer.
At high tide, you look right ...out at a mesmerizing view of sailboats, skiers, and other watercraft... whether the sea is calm or in a there is ''chop''. At low tide, you will be struck by the plethora of amazing flocks of water foul (not to mention more than a few oyster gatherers). Windswept's view is looking out toward Great Island.
Windward is close to many of Wellfeet's ocean, bay, and pond beaches, including its own. There are more bay , ocean, and pond beaches in Wellfleet nearby...more than any other town on the cape.Accessing any beach is easy because Wellfleet is narrowest town on cape.
for example, you can access a bay, ocean, or pond beach all within 5 minutes from one another.
Windward is within biking distance of the entrance to the Cape Cod Bike Trail. You can ride directly to trail from house without using a car. The Wellfleet Bay Sanctuary ( largest Audubon Society in MA. . Every day and evening you will have an abundance of activities from which to choose. There are the Shakespeare performances, nightly concerts, poetry readings, historical lectures, book signings, outdoor movies and inside cinema, a large combination of both cuisine eateries and family restaurant. All watercraft is available to rent for your use individually and there are many chartered options ( sail, fishing, sightseeing) as well.There are two amazing theaters in town that produce some of the most innovative and spellbinding performances all with professional actors. Every night, there are multiple professional offering making it difficult to choose which one to choose. Also, laying low at Windward watching the sunset from the deck is often a popular choice after spending all day at the beaches.
The Windwardt home itself has a very large open living space (LR, DR, and kitchen.) It has multiple clusters of seating areas so groups with differing agendas may enjoy an assortment of activities.... while remaining together on one floor. All floors are covered with authentic Oriental Persian rugs or hand made area rugs.
In the sitting/dining room there is a huge (4 seater) coach, a day bed, Morris chair, platform rocker, and Bose music system. This room also has a claw and ball antique table that can seat from 6 to 14 people depending on your needs. Unless watching TV or needing different rooms for different clusters of family members, this is ''everyone's'' favorite living space.
The LR also has many gliders and has equally fabulous water views. It has a seating arrangement that has 2 couches, a large matching stuffed chair and a rocking chair. This room has the upstairs TV with an extensive cable subscription.
The new (2012) gourmet kitchen has hand made wooden counter tops, custom built shaker style cabinets made of white ash, a huge island with recycle bins, new commercial grade stainless steel appliances (gas stove), and a lovely new slate floor. ( The woodworker had this kitchen featured in Fine Home Building Magazine. The amazing lighting artwork/ fixtures in the kitchen is the signature piece of the kitchen. The kitchen is provisioned for even the most sophisticated gourmet cook (between the pots and pans, baking dishes, every gadget imaginable, and more spices than you could imagine.
In both primary living spaces, you will feel like you are sitting right ''on top'' of the bay.
In 2013 we added a ''one of a kind '' double room outdoor enclosed shower with a dressing suite as well. The new outdoor shower has a private entrance from the master bedroom. There is a second outdoor shower adjacent to the back door.
The first floor has four bedrooms. The MB has a king size bed with a Temper-Pedic mattress and three 6 foot by 6 foot glider windows showcasing more fabulous water views. Also, the MB has its own sitting area, cable TV, a second Bose Music System, and its own master bath. The other three bedrooms all have access to the main bath off the center hall. One bedroom can be set up with a king size bed or two twin beds, another bedroom has a set of twin beds and the fourth bedroom has a double bed. All beds (other than MB have either custom made mattresses which are usually comfortably and always commented on.The latter was necessary because much of the furniture is authentic refinished voltage furniture or 1800 antiques.
There are two bathrooms on the floor with the bedrooms. The main bathroom was totally gutted and redone with the latest and most upscale products in 2015.This bathroom has a huge standing shower with glass on tow sides and abuts a huge tub ( both in height and length. Where there isn't hand plained wooden ( copied from master wood builders in the 1800 century ( all tongue and groove), the walls are white subway tiles.
The master bedroom private bath was just completed this summer ( also gutted at outset) It has a built in seat at end of shower that you can choose to heat. It also has a ceiling radiant heater in ceiling and an incredible amount of custom built cabinets. Many are built into walls so bathroom still feels airy and the glass door on shower is a practical and aesthetic choice that further enhances the MB bath. The till in shower, and floor is made of stone.
At Windward, the vacationer will have access to umpteen non fiction books about Wellfleet and Cape Cod. There are always plenty of top ten recent fictional books and fictional books either written by local authors and/or set in local cape cod settings.They are located next to a daybed that ask has magnificent views of the bay.
Our goal is to provide a unique home to Cape Cod vacationers. We are committed to insuring that Windswept provides a feeling of casual luxury, a home with exceptional water views, and a home that is exceedingly welcoming upon arrival. The house has a team of cleaning people including the owners who spend at least 24 hours between departing and arriving guests, cleaning/readying the house for our incoming guests. You, the vacationer, need only begin your relaxing, special and comfortable vacation. Every bed is made up with 600+ percale cotton sheets. Every room has been cleaned from top to bottom. Windward provides beach towels, bathroom towels, beach chairs, beach umbrellas, boogie boards, and other items upon request. It is our hope and wish that, with the fabulous breezes, the comfortable and luxurious feel of the house, and the majestic views, you, our guest, will feel immediately upon arrival. ACCEPT NON SHEDDING DOGS ONLY except when mutually agreed to permit otherwise.
There are 4 outdoor seating areas with tables, chaise lounges. One is in the pines in front of Windward where it is cool but not so breezy. One is specifically designed for use by those that are the renters in the MB. Another is one the second floor and while it is directly exposed to sun, the breezes off the water make it a favorite outdoor space. Those that want the same view and comfort can choose a patio directly below the deck
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Jun 27 - Aug 29 2026 | $7,500 | 7 nights | |||
Aug 29 - Sep 05 2026 | $6,500 | 7 nights | |||
Sep 05 - Sep 19 2026 | $5,000 | 7 nights | |||
Sep 19 - Oct 03 2026 | $4,500 | 7 nights | |||
Oct 03 - Oct 31 2026 | $3,500 | 7 nights |
Fees:
Last updated on July 24, 2026
Tom and Amy H.Fantastic two weeks at Windward!
To sum our experience up in a word - WOW. Windward really lived up to our highest expectations!Starting at the outside and working my way in:I have to start with the view - ever-changing tides, skies and sun kept us glued to the windows and living on the elevated deck. We had rented two paddle-boards (stored on the community rack a short two minute walk from the house) and had an amazing time exploring that landscape from the water.The property and landscape around Windward made our long time Cape renting (now owning) friends green with envy. Absolutely classic cape shoreline vegetation, white shell driveway and a hammock just made for warm afternoon gab sessions (our daughter and her friend) and naps (me). Moving closer to the house - the outdoor shower is fully tricked-out with everything we needed. I'm pretty sure that no one took a shower inside the entire two weeks we were there! I even showered outside in the rain - why not?!The house itself - classic Cape style. Bedrooms (all on the first floor) are cozy and the beds so comfortable with the thick soft mattress toppers we love. My wife and I had to shake ourselves every day when we woke up in the primary bedroom and looked out the big windows at that changing landscape. The primary bathroom almost feels like a ships cabin - there is just the right place for everything and plenty of storage space.The basement is dry, clean and kitted out with everything we needed for the beach and Cape explorations. There was lots of room to store our extra food and beverages and washer/dryer worked well.Saving the best for last - the upstairs living space. It worked perfectly for our group of eight family members. Starting in the kitchen - we ended up cooking most of our meals to avoid long waits at restaurants and to get some good pre-dinner cards and cocktails in. The kitchen has anything you could think of - including very sharp knives (a usual pet peeve I have with rentals). The kitchen has the most amazingly deep drawers - if you can't find something, just keep pulling out the drawer and you will find it! The ice maker cranked out ice for us and there were more spices than we could use. Also, the fish light fixture was everyone's favorite!In the living and dining rooms, there are ample places for everyone to sit including our favorite lounge chair reading nook with it's own little window. Our meals around the dining table were raucous and homey - just what our family loves. The
Stayed: July 2026 Submitted: August 06, 2026
Kelley J.Beautiful home in Wellfleet
Our 2 families stayed the week of July 11th (2026) and had the best time. It's a beautiful home in an ideal location. The owners made sure we had everything we needed. You truly only need to bring your clothes and food/beverages. We can't wait to go back. Thanks so much for hosting us! Sincerely, The Joice Family
Stayed: July 2026 Submitted: July 30, 2026
Shelley Lynn M.Great house great location
We stayed here for a week with two families. We are lucky enough to stayed here the second week of July. The house was very clean and had lots of amenities. I have never stayed at a rental with so many things provided for you. The views from the balcony were amazing. The owner had great communication and great recommendations. I would most definitely stay here again. Thank you for a lovely time
Stayed: July 2026 Submitted: July 27, 2026
Shelley Lynn M.Great house and great location
We had 2 sets of families that stayed here. We spent a week here, the second week of July. The house had tons of amenities and was very clean. The house had so many things were provided for us that I have never seen in a rental property. The views from the balcony deck were amazing. The host had great communication and great recommendations. I would stay here again most definitely. Thank you for a lovely time.
Stayed: July 2026 Submitted: July 27, 2026
William P.Wonderful stay at Windward
We had a wonderful stay at Windward for a week with family. It had plenty of room for the 8 of us, was well stocked with all amenities and had wonderful deck with a perfect view. The location was also excellent in Wellfleet close to the beaches, restaurants and other Cape attractions.
Stayed: July 2026 Submitted: July 15, 2026
John W.Stunning view, beautiful house
I stayed at Windward mid-May to mid-June, 2026. The view of Blackfish Creek as it flows into Cape Cod Bay is stunning and endlessly changing with the tide. The house, a custom built post and beam is beautiful and comfortable. It is well appointed and generously supplied. The owners who live in Wellfleet are most accomodating, helpful, and pleasant. My stay at Windward was a genuine escape.
Stayed: May 2026 Submitted: July 13, 2026
Theresa S.Perfect vacation
We truly enjoyed our 2 week stay at Windward this past June, 2026. The entire house, and most especially the kitchen, was very well appointed, the best we have ever seen. All we needed was a toothbrush and our clothing. The sunsets were stunning, the view was spectacular, it was extremely quiet and peaceful, sitting on the deck brought you to your zen place. The owners were extremely helpful with very good communication. We definitely would consider returning. Thank you for a lovely and relaxing trip.
Stayed: June 2026 Submitted: July 03, 2026
Josephine C.Wonderful Widward
We had a wonderful week at this exceptionally well-crafted and well-provisioned house. The post and beam construction exposes woodwork and rafters throughout, making the house a true work of art. The custom kitchen is amazing and fully supplied with every conceivable gadget and utensil. The owners provide every amenity throughout: the shelves are stocked with books and novels, the bathrooms and bedrooms are provisioned with linens and towels, and there is an indulgent outside shower and other niceties that clearly indicate the care and attention to detail paid by the owners. The layout of the house provides four cozy bedrooms on the first floor with a central staircase to the upper floor with kitchen, dining room, living room and lovely deck providing a spectacular view overlooking Blackfish Creek. As this is a west-facing view, the sunsets are spectacular. We took a number of lovely long walks on trails directly accessible from the house leading to Old Wharf Point and Cape Cod Bay. Also, the Wellfleet Audubon Wildlife Sanctuary is nearby and provides plenty of diversion for bird and nature lovers. We enjoyed our week at Windward and are looking forward to returning next year.
Stayed: September 2025 Submitted: November 01, 2025
Susan S.Perfect Cape Cod Getaway
We had an incredible stay at this stunning home! The house was immaculate, thoughtfully stocked, and decorated with beautiful things. The beds were very comfortable. We enjoyed the spacious outdoor shower, and a convenient foot rinse station after visiting the beach. The views of the water and sunsets were breathtaking from many spots inside and outside the house. We were able to store and use our kayaks a short walk from the house. The home is a short drive from the Drive-in theater; town; Wellfleet harbor; and pond, ocean, and bay beaches. The owners are very responsive, and gave us a tour of the house at the beginning of our stay. Highly recommend!
Stayed: September 2025 Submitted: September 24, 2025
Kristin H.Another Outstanding Stay at Windward
This is our fourth year renting Windward and I believe our second time renting for two weeks. As always the house was clean and extremely well stocked with hosts ensuring you just need to bring yourself and your clothes! The hosts make upgrades every year so the house is always in the best shape. The house was perfect for hosting various family members over the two weeks with enough space for lounging that no one is ever in anyone else's way. The views, especially the sunsets, are stunning. Very peaceful location yet close to everything on the Outer Cape.
Stayed: August 2025 Submitted: September 21, 2025
Danielle D.Beautifully Maintained, Fully Stocked, and Close to Nature
We had a wonderful week at this beautifully maintained home. Everything was spotless, tastefully decorated, and clearly cared for with love. The house was stocked with absolutely everything you could possibly need — from plenty of fresh towels to a fully equipped kitchen. Because the home is so nicely appointed, families with young children will want to be mindful, but it's a lovely space for creating special memories together.The location was great. A short walk took us to a nearby marsh area full of fascinating ocean wildlife — we spotted crabs, shorebirds, and other beautiful coastal creatures. Wellfleet has many activities in addition to numerous beaches such as an animal sanctuary and drive-in movie theatre.This is truly a perfect home for a relaxing family getaway.
Stayed: July 2025 Submitted: September 01, 2025
Robin Z.Wonderful stay at Windward!
The Windward house sits on a perch overlooking Blackfish Creek, Fox Island Conservation, and all the way out to the Great Island's cliffs. It is a slice of heaven. The view is mesmerizing! This post and beam house is beautifully constructed with a layout that takes advantage of the views. Our family was very comfortable in the 4 bedrooms with 2.5 bathrooms along with the best outdoor shower. The de-sanding station at the back door was used every day. The house is extremely well supplied with anything you would need for your stay. We had not been to the Old Wharf neighborhood as we have rented on Indian Neck for many years. We loved this part of Wellfleet. It is a gem. Every day we walked down to the point for a swim. Elisabeth and Douglas were attentive hosts and have set up an incredible vacation spot! Thank you!!
Stayed: August 2025 Submitted: August 25, 2025
Jenifer S.Perfect Wellfleet Getaway with Stunning Views and Exceptional Hosts
We had an absolutely wonderful stay at Windward! The location couldn't be better - close to everything yet peaceful, with gorgeous water views that make every day feel more magical. The home itself is spacious, with large comfortable room that are impeccably clean and meticulously maintained. It's beautifully decorated with stunning local artwork, giving it a warm and authentic Cape Cod feel. The owners have truly thought of everything - every amenity you could possibly need is stocked and ready. On top of that, the hosts are fantastic, responding immediately to any questions or needs. This is the kind of place you look forward to coming back to year after year.
Stayed: August 2025 Submitted: August 09, 2025
Ann M. M.Windward Wonders
Windward is an extraordinary vacation rental. Located in a beautiful spot in South Wellfleet, the house immaculately clean, well-equipped, beautifully decorated and, most important, warm and welcoming. We have visited Wellfleet for a summer vacation for many years, and no home we have rented comes close to Windward. The owners have thoughtfully paid attention to every possible need of vacationers --- there are beach towels, chairs and toys; the kitchen is beautifully appointed and provides cooking basic necessities and extras like a variety of spices; the sleeping areas are designed for comfort and come with all grooming and beach necessities much like a high end resort; and everywhere, there is information about the house, the area and shore living and there are books of all kinds from beach reads to classics.With all of this comes the showstopper: the view! Be prepared for gorgeous sunrises and spectacular sunsets from the deck, dining room and master bedroom. Windward is a true feast for the senses. We will be back! Nothing less will do and we are grateful our hosts, Elisabeth and Douglas, have shared with us the opportunity to experience living in their beautiful home, if only for a week.
Stayed: July 2025 Submitted: August 07, 2025
Elizabeth H.Another Perfect Stay at Windward
This was our third summer staying at Windward, and it continues to exceed expectations. The owners clearly take pride in the home and consistently attend to every detail. The house and grounds are immaculate, with thoughtful touches throughout that make it feel both luxurious and welcoming.The setting is peaceful and beautiful, with a nearby marsh that’s perfect for kayaking and paddle boarding—something we look forward to every year. The house is ideally located: just a short drive to the town center and some of the most stunning beaches on the Cape.Inside, the kitchen is a dream for anyone who enjoys cooking. It’s incredibly well stocked with everything you could need—high-quality pots and pans, blenders, utensils, and even an impressive selection of spices and pantry staples. The open common area is perfect for group gatherings, and the deck offers gorgeous views and a lovely spot to unwind at the end of the day.Windward has truly become a special place for our family. We hope to return next summer.
Stayed: July 2025 Submitted: July 27, 2025
Sarah F.Wonderful!
This is a lovely house with a great view in a location that is close to beaches, town and fantastic bakery. Our family loved all the thoughtful touches and the cleanliness. Perfect for a family. Windward is a great find. Don’t pass it up!
Stayed: July 2025 Submitted: July 22, 2025
DalyFirst time visitors, not last time visit
Our family recently returned from a week long stay at Windward. 2 adults, 10 yr old, and Old English Bulldog. We had an amzing time and can say it was one of our best vacas!The home is beautiful and the homeowners are lovely. They were available before and during our stay for questions. The care and love put into the home is evident in every Nook and cranny. Well appointed with every amenity you could imagine. The homeowner was there to welcome us on our arrival and walk us through the home. Close to beaches, downtown, resteraunts and shopping, but on a quiet street minutes from the main road. Be prepared for incredible sunsets!!!!Outdoor shower...wow!! Master bath shower, I never wanted to leave. Beds..more comfortable then our own. Haha. The kitchen, everything you need is there! The artwork, beautiful!!Whether your swinging out front on the hammock, taking in a view and some shade out on the lower patio, enjoying nature by the seating area off the master bedroom, curling up on the chaise in the dining room, or enjoying the view of the bay on upper deck, there are ample spots on the property to start your day or unwind.
Stayed: June 2025 Submitted: June 30, 2025
Carol H.Wonderful house!
Our stay in this fabulous property included 5 women, from all parts of the country. The magnificent view, and the traditional Cape Cod decor gave them all a great introduction to what The Cape is all about.The house has everything you could ever need! And I mean, EVERYTHING! High end beach chairs, beach games, scores of puzzles, beautiful glassware for the libation of your choice….and, not only are the bathrooms equipped with hairdryers, toothpaste, etc, but each person was left a shower caddy with shampoo, body wash, bug spray, a loofah sponge….and more!The deck is the perfect spot to take in the ever changing view. And, if you can get yourself to leave it, just a short drive will get you to some beautiful beaches. We also enjoyed the short drive to Ptown for shopping and drinks.Douglas and Elisabeth are incredible hosts. What a gem!!
Stayed: June 2025 Submitted: June 29, 2025
Robin S.Well appointed
Our three adult children and their significant others joined us for a week at Windward. We were all quite comfortable. When we weren’t exploring the Cape we were cooking, playing games, puzzling or watching movies at the house. This home has many gathering areas as well as many quiet reading nooks, perfect for our group. When we are together, we enjoy cooking. Never have we stayed at a vacation home with such a well stocked kitchen. The views from the home are stunning and all the activities we were interested in doing were easily accessible from the home’s location. We hope to return in the future.
Stayed: May 2025 Submitted: May 15, 2025
Kristin H.Another Outstanding Stay at Windward
This is our third consecutive year renting Windward for our extended family. Elisabeth and Doug are extremely thoughtful hosts, ensuring that their guests have everything they need in a beautifully maintained house to have an exceptional vacation. The house is well equipped, so much so that you truly only need to bring your clothes! All the beds are very comfortable, the kitchen extremely well equipped and there is plenty of room for 8 adults to spread out. The location is peaceful with gorgeous sunset views and convenient to everything on the outer Cape. We will definitely be back for year 4!
Stayed: August 2024 Submitted: October 24, 2024
Kristin H.Glorious Stay
This is our third consecutive year renting Windward for our extended family. Elisabeth and Doug are extremely thoughtful hosts, ensuring that their guests have everything they need in a beautifully maintained house to have an exceptional vacation. The house is well equipped, so much so that you truly only need to bring your clothes! All the beds are very comfortable, the kitchen extremely well equipped and there is plenty of room for 8 adults to spread out. The location is peaceful with gorgeous sunset views and convenient to everything on the outer Cape. We will definitely be back for year 4!
Stayed: August 2024 Submitted: October 22, 2024
Kathryn A.Spectacular family vacation at Windward!
I had trouble finding just the right spot for my husband’s 75th birthday celebration where we could accommodate his four grown children and his three year old granddaughter as well as ourselves. Windward had all the answers! It has the perfect location with a gorgeous view and quiet surroundings. The kitchen is fully loaded with every spice and utensil you could need. Before you go grocery shopping make sure you check this kitchen out so you won’t buy something that’s already there! From the beach chairs and toys to the explicit directions about whatever you might need, Douglas and Elizabeth provide everything down to the last detail. It is so homey there. It does not have the coldness that some other rental properties do. it is close to ocean beaches, bay beaches and pond beaches. Be sure to check them all out as the sticker you need for your car will allow you to park at any and all of these spots. The outdoor showers are fantastic after a day at the beach. The gorgeous deck is the perfect place to unwind after a long day and watch the beautiful sunset. There is a fantastic grill out on the deck that we didn’t use in this circumstance, but I would if I went back again. The landlords are very attentive to your every need and will come and help you in person if need be. It was perfect for everyone from the three year-old to the 75-year-old! If you’re looking for an authentic Cape Cod experience, look no further than Windward!
Stayed: August 2024 Submitted: September 12, 2024
Amy D.Wonderful home rental
This was our first stay at Windward, with 8 people. The home is very clean, comfortable and well-appointed, and the view is fabulous. There is access to the bay beach via Indian Nauset Trail nearby, it was very nice for walking. It was also easy enough to drive a short distance to launch our kayaks. The neighborhood is quiet. The location is also very convenient to popular spots in Wellfleet. Douglas and Elisabeth provided all the beach items needed, which truly saved space when packing the cars. They also provided shower items, sunscreen and bug spray for each person. The kitchen is updated and spacious. The outdoor shower is large and private. We will definitely consider staying at Windward again next time we visit Cape Cod.
Stayed: August 2024 Submitted: September 05, 2024
Cathy E.We loved Windward!
We spent two glorious weeks at Windward with our family - 4 adults, 2 teens, and 2 dogs. It was perfect for our group - very unique house with a high level of craftmanship - very clean and lots of of amenities. The upstairs living area has a gourmet kitchen and big windows that provide amazing views of the marsh, tides, and sunsets. The outdoor shower is fabulous - the best we have encountered on the cape. A good location on a quiet road - with easy access to walking trails, including along Blackfish Creek. We enjoyed meeting the incredibly nice and responsive owners. We would definitely consider returning to this beautiful and charming house.
Stayed: July 2024 Submitted: August 11, 2024
Elizabeth H.Another perfect vacation at Windward!
Our family recently returned from another perfect 2 week stay at Windward. The house, like last year, is immaculate and incredibly well-appointed. Douglas and Elisabeth are wonderfully attentive hosts and made sure we had everything we needed, and more. It is clear they put a lot of thought and care into providing a comfortable and luxurious stay for their guests. HIghlights of this beautiful cottage nestled in Wellfleet were breathtaking views of the marsh at sunrise and sunset, taken in from the expansive deck, and kayaking in the marsh. Note - Jack's boat rentals delivers boats right down to the marsh for Windward guests. We have already booked our stay at Windward for summer 2025 and cannot wait to be back!
Stayed: July 2024 Submitted: July 30, 2024
Judith C.Spectacular views and comfort galore!
I just spent a very relaxing week at Windward. The home is equipped with everything one could possibly need with all the comforts of home. My family loved the deck and the wonderful ever-changing views of Blackfish Creek. I spent a lot of time in the reading nook with a beautiful view of the water. Even if someone was watching tv, the nook was quiet, comfortable, and peaceful. The home has space for everyone with a thoughtful layout. This is the perfect home for a family to spend time together as well as relax in your own space. The beds are amazingly comfortable too! The quiet surroundings and a walk along Nauset Trail adds to the charm of this splendid location.
Stayed: June 2024 Submitted: July 06, 2024
Nicole G.Another Amazing vacation stay at Windward!
Having stayed at Windward in May of 2021, my family and I were so delightfully surprised that Windward was available for this spring as well. It was wonderful to spend 4 weeks, with my family, including my husband, 2 sons, and 2 daughters. While I was expecting Windward to be special; having spend a couple of weeks in 2021 also, I had no idea how much more special I was these 4 weeks in 2024.The Ingrams provided caddies for each individual vacationer to use for the outdoor shower, which was amazing! The Ingrams supplied much more to use in kitchen; for example, Dunkin Donuts coffee pods for kuerig, coffee beans/ ground coffee for drip coffee maker, teapot with umpteenth amount of types of teas. The amount of spices, sugar, flour, bisquick, utensils, ect, definitely came in handy for easy cooking. My children loved pancakes and maple syrup (provided at Windward) for me to make a great “d fashioned “ breakfast.The amount of linens, toiletries, extra sheets, toilet paper, paper towels, napkins, medicine available to access in bathroom cabinets, for which all we needed, and very thankful items were available to us.Windward was extremely clean and organized, which felt very welcoming to us right away. We really appreciated all of the live indoor plants, from in each bedroom, to the dining area. Lots of plants and beautiful bushes outside for us to enjoy as well. We also enjoyed on sunny days overlooking the water, low and high tide, and gorgeous sunsets, either viewed from the dining/ living room area, to relaxing on the top deck. Sure was breathtaking at times.My family and I highly recommend Windward in all areas as five stars in every aspect of our vacation. We will definitely put in place with our plan to return either spring or fall 2025, for which we prefer coming on either side of summer, traffic is a bit less, yet many , most restaurants and amenities are available as well.
Stayed: May 2024 Submitted: June 21, 2024
Karen and Neil S.Outstanding Cottage and View
Our family returned to this cottage a second season because of the unsurpassed view and peaceful surroundings. The upstairs contains a fully-equipped kitchen with modern appliances. Since the cottage is minutes from Hatch's fish market, we chose to cook fresh seafood every evening. We enjoyed sitting on the upstairs deck every morning with our coffee and to view the wonderful sunsets. The king sized beds on the lower level are so comfortable we all slept comfortably from the first night. The location also makes it easy to bicycle from the cottage to the rail trail, the Old Wharf and ocean view drive.
Stayed: June 2024 Submitted: June 21, 2024
Debbie H.Breathtaking water views and sunsets!
We spent a wonderful week at Windward. The water views and sunsets were incredible. The post and beam style upside down house was beautiful. There were fresh cut flowers in all the bedrooms. The potted plants that didn’t need watering added to the ambience of the home. The house was sparkling clean.The kitchen had everything you could possibly need. Windward is close to bay, ocean, and pond beaches. Also close to restaurants, grocery stores, galleries, shops, boutiques, rail trail and Audubon Sanctuary. We spent a relaxing week in a beautiful home!
Stayed: September 2023 Submitted: November 11, 2023
Lillian H.Wonderful Family Vacation
The Windward was an amazingly beautiful home. The woodworking and all of the added custom details was just beyond anything we had imagined. The view from the cottage is incredible and we spent time watching the gorgeous sunsets each evening. There was plenty to do and everything was a short drive. The home was beautifully appointed and had absolutely everything that anyone could need. This was a fantastic place to take a vacation. Can’t wait to return!
Stayed: September 2023 Submitted: October 31, 2023
Kristin H.Another Outstanding Stay at Windward
After spending one week at Windward in 2022, we decided it wasn't enough and booked two weeks in 2023 and thrilled again with our experience. The property is lovingly cared for by the owners and every amenity is taken care of. The kitchen is wonderfully stocked with essentials, there are plenty of towels and beach towels and all the beach items you could possibly need. I particularly like the comfort of Windward...there is plenty of space for everyone to spread out and not be on top of each other and many cozy options for curling up to read a good book, watch the gorgeous sunsets, the ever changing tidal marsh views or tune out to TV. I also appreciate the modern bathrooms and the TWO outdoor shower spaces. The location is perfect...very quiet and peaceful but a short ride to restaurants, ocean and bay beaches and the Wellfleet Kettle Ponds. We even brought our bikes this year and easily biked to the Cape Cod Rail Trail. Elisabeth and Douglas are super conscientious h
Stayed: August 2023 Submitted: October 27, 2023
Robert G D.Excellent rental
Certain homes have a pleasant aura about them, we found Windward to be one of them. Four of us rented Windward in September and enjoyed an excellent week. The location was perfect for enjoying the outer cape, close to many beaches on the bay and ocean side, very good restaurants and attractions nearby. Windward was very clean upon arrival and loaded with a fully equipped kitchen. we enjoyed many meals on the upper deck, overlooking a spectacular view . The house also had all of the necessary amenities needed to make an enjoyable vacation. The hosts were very accommodating . we will return to windward.
Stayed: September 2023 Submitted: September 26, 2023
Rosemary D.Heaven on earth
The owners of Windward went above and beyond to ensure we had an unforgettable two week vacation. First, the setting on the water is spectacular with views for days! The location is fantastic- close to beaches and a quick drive to town. The house is completely stocked with anything and everything you would need. The kitchen has anything a gourmet chef would need, including dozens of spices. We were also provided with coffee pods for the Keurig and new coffee for the regular coffeemaker! The bedrooms all had clean sheets and towels, plus fully stocked bathroom caddies for each person that included new shampoo, soap, bug spray, sunscreen, and many other items. The home is also stocked with everything you need for the beach including beach towels, blankets, chairs, umbrellas, coolers, etc. The owners are readily available for any questions or concerns and could not be nicer. The house had vases of fresh cut flowers upon our arrival in every room! The decor is cozy and comfortable, with beautifully updated bathrooms and kitchen. The outdoor spaces are also great, and there are very handy outdoor lines to hang towels after a day at the beach. We loved the large, newer outdoor shower as well. The owners have thought of everything and we cannot wait to return!
Stayed: August 2023 Submitted: September 05, 2023
Nancy K.Idyllic Escape
My family recently had the privilege of staying at this lovely vacation rental, and it truly exceeded all expectations. From the moment we arrived, we were greeted by the most breathtaking sunsets which we enjoyed every afternoon from the well furnished deck.The rental itself was a haven of comfort and convenience. It was abundantly clear that Elisabeth and Douglas had put a lot of thought and care into making sure every guest's needs were met. The place was incredibly well-stocked – from the kitchen essentials to the bathroom toiletries to a great selection of books, we lacked for absolutely nothing. This attention to detail made our stay so much more enjoyable, as we didn't have to worry about running out for basic supplies.What truly sets this vacation rental apart is its prime location right on the bay. The proximity to the bike trail was another highlight – we spent our days exploring the area on two wheels, surrounded by nature's beauty. Our daughter/son-in-law were even able to commute there from the Provincetown ferry on their bikes! Marconi beach was only a 5 minute ride away and is truly one of the most beautiful beaches on the Cape.In conclusion, our stay at Windward was wonderful. The stunning sunsets, the well-thought-out amenities, the bay-side location, and the evident passion that went into its creation made it a true gem. If you're looking for a place to unwind, reconnect with nature, and bask in the comfort of a home away from home, Windward should be your top choice.
Stayed: August 2023 Submitted: August 29, 2023
Elizabeth H.Magical stay in South Welfleet!
This was truly the most magical vacation home we have ever stayed in. The views alone are enough to recommend this home, but there is much, much more. The house is fully stocked with absolutely everything you could ever want or need - from cooking supplies to towels, extra blankets, plenty of beach reads, and even a personal caddy for every guest that includes all the things you might forget, like sunscreen, shampoo, aloe, and razors. The decor is casual and elegant with plenty of seating for a spectacular view of the marsh - whether from inside on a cloudy day or sitting on the deck, or on the hammock in the ample front yard. The Ingrams have thought of everything to make guests feel welcomed and cared for. We have already booked our stay for next summer and cannot wait to return.
Stayed: July 2023 Submitted: August 07, 2023
Tara M.Windward Forever!
We had a magnificent week at Windward. The property and setting were even better than the photos and the owners could not have been better hosts. My parents -- ages 86 and 91- enjoyed the master bed and bath and spent days out of the sun on the lower patio enjoying spectacular views of Pleasant Point and Great Island. the rest of us enjoyed lounging on the 2nd floor enjoying the cozy spaces, fabulous kitchen and spectacular views. Windward is a real home -- and becomes that for the people who stay there. We will treasure our memories from this week -- and are so grateful to Elisabeth and David for taking care of us and their lovely Wellfleet retreat.
Stayed: July 2023 Submitted: August 03, 2023
Host response
"Tara, Thank you for providing a lovely review of Windward"
Karen S.Windward Wonder
On a quiet walk in Spring of 2022,we came upon Windward cottage. We experienced awe and admiration of the architecture and view of the marsh. We found this home listing and immediately contacted the owner to reserve for Sprng 2023. Our wonder expanded when we first entered the cottage on June 3, 2023. The views of the marsh from the living areas and master bedroom are unsurpassed. Our family of six decided to prepare dinner in the fully-equipped, well-appointed kitchen every evening. When it was my turn to prepare dinner, I would turn on classical music and dreamily take my time in the moment, while looking at the view. Hatch's Fish and Produce is nearby in the village of Wellfleet. Most of their seafood is fresh daily, as well as oysters from their own beds. A rainbow appeared over the marsh our first morning. Days were spent bicycling and hiking the known and less known trails around Wellfleet, as well as gazing at the ocean from the town beaches. The ponds are nearby and offer swimming. We brought a kayak, which can be launched in some ponds and the marsh below the cottage. Evenings were spent reading or working puzzles, listening to the wind and sometimes the rain. We slept well in the comfortable beds. We all appreciated the on-suite bathroom and shower, extra nearby bathroom with tub and shower, upstairs toilet near the living area, and outdoor shower. Linens and towels are provided, as well as a washer and dryer. There are plenty of restaurants, shops and art galleries nearby, as well as theatre, and the Wellfleet Drive-in. Our daughter and her fiance biked from the cottage to the Provincelands and back in four hours. We discover something new every year, and Windward is a joy to return to each day.
Stayed: June 2023 Submitted: June 19, 2023
DavePicture perfect!
What a vacation this was! Douglas and Elisabeth gave us extensive information on the house and town before we even arrived. Upon our arrival, Elisabeth greeted us warmly, had a few thoughtful "welcome to our home" gifts, gave us full tour of the house, and even strolled the neighborhood with us to show us where the trails to the water were. They checked in to be sure we were happy with everything.The house is even better than the photos show. There are so many nice little decorating touches that you just can't capture in a photograph. It is all sea themed and often Wellfleet themed, with paintings and sculptures by local artists. It manages to be roomy and cozy at the same time. The post and beam construction surrounds you with beautiful wood . The kitchen is incredibly well stocked. The custom designed cabinets make excellent use of space, the appliances are new, and whatever you need is there and organized meticulously. The bedrooms are charming, the beds were very comfortable, Linens and towels are supplied. There was ample seating in both the dining room and living room, and no less than four outside sitting areas. The views of the water and the sunsets are spectacular. If you don't like sand, just sit on the deck, enjoy the sun, and be surrounded by water views. The neighborhood was quiet and delightful to stroll and bike. The woodworking in the master bath is simply beautiful and all the bathrooms look like they have just been remodeled. Even the fixtures are elegant. It could be the cleanest house we have ever stayed in.May can be a bit unpredictable, but we were blessed with a spectacular week of sunny weather in the 60's and 70's. There are lovely trails (in Wellfleet at Marconi, in the Province Lands, and the Audubon Sanctuary), numerous kayaking sites, a wonderful gym called Heart Core, Catholic Masses are available in Wellfleet, P-town and Orleans, lovely bay and Ocean beaches, and of course the Cape Cod Rail Trail. We were able to find gluten free fare at Montano's, Three Fools, the Rail, Far Land Provisions and PB Boulangerie. Wellfleet Marketplace is great store that has just about everything and is oozing with local flavor!This vacation was picture perfect.
Stayed: May 2023 Submitted: May 20, 2023
Cameron R. Dianne A.A month of quiet and beauty
My husband and I decided to try staying a month at one of our favorite places, Wellfleet, and were so lucky to find Windward. The beautiful, ever changing bay and marsh became our best friend. We enjoyed a wide range of weather including many beautiful fall days. The house is very well equipped and has great character. Now back at home, I miss being there!
Stayed: October 2022 Submitted: November 04, 2022
David F.Stellar Views, Great House
If you live for amazing Cape views this is the house for you. With views on both levels, the experience staying for a week was just an amazing delight. For those concerned with other essential things like comfortable beds and a well-stocked kitchen., you have also found the right place. Top of the line appliances and a fully stocked kitchen are prime features of this kitchen. There is also a really nice deck that overlooks the Bay. Finally, the house is very well stocked with beach equipment -- umbrellas, chairs and much much more
Stayed: August 2022 Submitted: September 22, 2022
Kristin H.Great House, Great Views
Watching the ever changing landscape of the tidal marsh, gorgeous sunset cocktail hour on the deck, plenty of comfy couches for lounging and reading and every detail thought of sums up our week. Elisabeth and Doug have created a beautiful oasis and are super conscientious in ensuring you have the best, more carefree vacation at their house. This is the 7th house I've rented on the Cape over the last 20 years and definitely the best. Honestly the photos don't capture the specialness of this home.
Stayed: August 2022 Submitted: September 11, 2022
Perry & J.Lovely Wellfleet home
Our family recently spent at week at Windward and thoroughly enjoyed the house and the location. We were a group of 8 adults, 4 couples, and one very happy Bichon Frise. The house is a wonderful work of art and was immaculately clean and well cared for. The owners were very attentive and responsive, both in advance of the vacation as well as during our stay whenever a need arose. We we all charmed by the location, the peace and quiet, and the spectacular view from the deck, the grounds, and many rooms in the house. The sunsets are definitely amongst the best we've ever seen in Wellfleet.
Stayed: August 2022 Submitted: September 04, 2022
Michael I T.Perfect retreat
From the location overlooking an inlet to Cape Cod Bay, the property and surrounding areas are a perfect setting. The house is clean and comfortable. Elisabeth and Douglas provide all the amenities for staying at the house or going to the beach. The house is located within a short driving distance to 20 different beaches, the town and many restaurants. They were very helpful in making recommendations for beaches, restaurants or sites of interest. I've already discussed with them coming back next year. I would not hesitate to recommend this property.
Stayed: July 2022 Submitted: July 27, 2022
Abe G.AMAZING
My wife and I stayed at Windward for seven nights at the beginning of July. In one word, our experience was "exceptional." Elisabeth and Doug were wonderful, attentive, hosts who provided is with all the information about Windward that made the week fly by. So the sunsets from the deck are amazingly beautiful; the changes in the bay waters are a wonder to behold; the accoutrements in the house are very tastefully and aesthetically pleasing; very user-friendly kitchen, SPOTLESS house, quiet, and serene. Close to restaurants and five minute drive to center Wellfleet. We highly recommend staying ate Windward. What a find!
Stayed: July 2022 Submitted: July 12, 2022
Mairead C.Amazing Wellfleet Sunsets
Awesome sunsets in WellfleetGuest Review: My husband and myself along with our 4 adult children had the pleasure of renting Windward the last week in June. We have traveled and rented homes often and this was by far the most organized and well stocked home we ever rented. From bedding to beach toys to a state of the art stocked kitchen they had it all! There is nothing you needed to bring. My two Favorite parts were how everything in the house was labeled and how each room had shower caddies for each person filled with toiletries, sunscreen, after sun lotion, razors, and so much more.Of course the icing on the cake was the most beautiful views overlooking the water along with breathtaking sunsets.Elisabeth and Douglas supplied us with so much literature regarding restaurants, beaches , ice cream places, cape cod history and more. They were easy to communicate with before and during our week visit and were available to help us the when asked. They even held on to our daughters bathing suit that we left behind so we could get it back!Thank you for opening your beautiful home to renters and we look forward to renting again.
Stayed: June 2022 Submitted: July 09, 2022
G H.Windward
I can’t think of a better place to spend a week on Cape Cod than at Windward. Located on a tidal marsh off of a quiet dirt road, the setting felt remote and yet was only minutes to beaches,trails, restaurants and galleries. The house itself was charming, warm, and rustic - beautifully designed and maintained. The furniture was lovely, and the kitchen was equipped with everything you can think of. The deck, which overlooks the marsh, (as do most of the rooms in the house) was the perfect place to eat a meal, watch the sunset and just relax. Elisabeth sent us lots of information about Wellfleet even before we arrived, and clearly attends to every detail to ensure a wonderful vacation. We would definitely stay here again.
Stayed: May 2022 Submitted: July 07, 2022
Patricia D.Little Piece of Heaven
I booked Windward in early January. Having family from the Cape, we felt it was time to get back “home” even if only for a week. I came upon Windward as I’ve used this booking site in the past and have never been disappointed. I’ll list the pros and the cons.Pros: location is excellent for those who like to be closer to PTown, Nat’l Seashore, and a bit less craziness the Cape can have! The house is very well stocked with kitchen requirements, extremely comfortable, organized (something I appreciate!), and the sunsets are glorious! The house matches the pictures on the website; quincentennial cape cod appeal. We loved the house.Cons: We went in early June when ticks are just waking up looking for hosts. Thanks goodness our small non-shedding dog is white! I am used to doing tick checks living in a mountainous area, but the ticks were pretty bad. Spraying the grassy area around the house would help, but may not be allowed for conservation purposes. We all did tick checks and managed it.Too much contact prior to arrival, and during stay with owners. I appreciate the owners being selective with whom they rent to. I spoke with the owner, Elisabeth, for over an hour when interested in booking Windward, we were sent a 17 page instruction booklet, asked to have a half hour conversation day before we arrived, along with being asked for an hour in person orientation upon arrival. Too much and not necessary. It felt like a lot of “work” just to begin our vacation. This regiment might be something to consider changing. It felt a tad intrusive.All in all, we had a lovely time. The owners of Windward love their home, and it shows.
Stayed: June 2022 Submitted: July 05, 2022
Anne T.Oasis on the Water
Windward is a wonderfully clean and perfectly quirky home located central to delicious restaurants, national seashores and all kinds of outdoor activities (hiking, biking, mini golf, etc.). The hosts stock the house with everything you could imagine, making packing a breeze. The home is big enough to provide privacy for anyone looking for it and quaint enough to get in some great family time. I highly recommend Windward!
Stayed: June 2022 Submitted: July 05, 2022
Joyce K.Beautiful home - lovely views - very comfortable
Windward is a lovely home with the most beautiful views. The kitchen has everything you will need and you can watch the gorgeous sunsets from the deck or from the living room and dining room. Owners are very responsive and respectful of guests' privacy. Location is lovely - beautiful walk on dirt roads to the bay; close to the best French bakery on the Cape; very close to Marconi Beach and an easy ride into Wellfleet or Provincetown.
Stayed: May 2022 Submitted: June 28, 2022
Host response
"Joyce and Annie, Thank you ever so much for writing such a lovely review of Windward.E & D"
Rebecca S.Wow!
Wow! This rental has it all! Beautiful, COZY home…all the amenities you could ask for…the most stunning view and sunsets….close to all the great ocean beaches….an amazing outdoor shower….books, beach chairs, beach towels, beach games….you do not need to bring anything but a good relaxing vibe to this home! We had a great stay with seven adult family members! Wellfleet is just beautiful….can not wait to come back!
Stayed: June 2022 Submitted: June 27, 2022
Host response
"Rebecca and Jim,We are so pleased that you enjoyed Windward, Wellfleet Windwards amazing sunsets, and all the amenities. Thank you for taking the time to write a review.E & D"
Member since 2021
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