Wellfleet Vacation Rentals

(7 rentals)
Honeymoon Cottage

1 BR | 1 BA | Sleeps 3 | Quick View

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Key Amenities

  • Beachfront
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Adorable cozy cottage across the street from Mayo Beach but set back about 100ft off the road in a private setting on the bayside of Wellfleet harbor. Walk to the best playhouse on Cape Cod as well as to tennis courts, basketball courts, and restaurants.A short walk will take you to the center of town; ...

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Property Type

Wellfleet Cottage

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Stunning Water Views from ''Windward'' on the Bay

$396

avg/night

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Key Amenities

  • Pet Friendly

About this property

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 ...

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Property Type

Wellfleet House

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Contemporary 3BR Saltbox Nestled in Woods

$243

avg/night

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About this property

Chequesette Neck area in private woodland setting. Large wrap-around deck with beautiful sunset views. Near lovely bay beach suitable for families with small children. Convenient to library and town center. Bright, airy, open design with cathedral ceiling. Accented with soothing colors of sand and sea. ...

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Property Type

Wellfleet House

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Waterfront Cape Cod Cottage with private beach 5 bedrooms

$1006

avg/night

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Key Amenities

  • Pet Friendly

About this property

Enjoy one of the Chequessett Inn's original bluff cottage's built in the early 1900's on Mayo Beach by Captain L.D. Baker. This beautiful large waterfront cottage has panoramic views of Wellfleet Harbor stretching all the way across to the Cape Cod National Seashore's Great Island. In the evening, enjoy ...

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Property Type

Wellfleet Cottage

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Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

$325

avg/night

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Key Amenities

  • Beachfront
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool

About this property

Welcome to Our Spectacular Beachfront and Waterfront Bay Cottage Located on Lieutenant Island in Wellfleet, Massachusetts. An Internationally and Regionally Featured Property. It's in a Very Picturesque and Private Location with a Western Exposure. It has a Flowing Open Floor Plan with the Living, Kitchen ...

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Property Type

Wellfleet House

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Views. Beach. Privacy. Gracious home on a hill has it all.

$600

avg/night

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Key Amenities

  • Pet Friendly

About this property

This home is charming, well-loved, spacious, and comfortably-furnished. Most rooms have views of the harbor and out to Great Island and beyond. Dine on the three-season porch with bay breezes, watching the boats coming and going in the harbor. Enjoy spectacular sunsets from the house, porch, and large ...

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Property Type

Wellfleet House

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Summer/Fall/ Winter/Spring Getaway for up to 2 Families.

$478

avg/night

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About this property

This 3,000 sq ft. plus rental is equipped like a home with quality furniture, appliances, finishes and every amenity you could think of to make your vacation complete. Our home boasts an open floor plan, with 4 bedrooms - one downstairs (queen bed), two upstairs (one with two twin beds and another with ...

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Property Type

Wellfleet House

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Wellfleet Vacation Rentals

Find a Wellfleet vacation rental for a unique trip

Wellfleet's uniqueness is easy to appreciate in so many ways. It's a quaint town that blends together an eclectic collection of artists, a surprisingly diverse set of dining options, a cute little downtown area, and almost too many outdoor attractions and activities. The fact is, you have to experience it to appreciate it. So, if you're considering booking a Wellfleet vacation rental, don't hesitate. If you're staying somewhere else on the Cape, make sure a day trip (or two) to Wellfleet is on your list.

The town is one of the world's best oyster beds and has had that reputation and industry for decades. Its devotion to shellfishing permeates so many aspects of vacationing in Wellfleet. The restaurants have extremely fresh seafood options, and there are events and community gatherings celebrating the the connection and reliance on ocean fare. Travelers come from all of the world and all over New England to enjoy the Main Street in Wellfleet so don't miss it.

Our vacation rental options range from romantic cottages for a couple to houses for an entire family. Where your rental is located in Wellfleet depends on what you want proximity to, but ultimately most of the town and attractions are quite walkable and/or bikeable. Regardless of location, you'll enjoy the space, comfort and privacy of home, often for less than the cost of booking a hotel room.


Wellfleet, MA travel advice

Many people have heard of Wellfleet oysters and maybe have preconceived notions about the Outer Cape. Here's the deal:

Wellfleet will surprise you. It has diehard, annual visitors who flock to book their Wellfleet rentals from Memorial Day to Labor Day months and months in advance. If you're considering booking something around OysterFest, then you better get going, like now! If you don't end up staying in town, you still should 100% prioritize visiting one or some of its famous summer spots. If forced to choose, we'd recommend a day trip that includes a walk around the galleries on its picturesque Main Street before heading over for some live music and food at the Beachcomber so you can bask in the glory of Cahoon Hollow Beach.

If you're lucky enough to find and book a vacation rental in Wellfleet, be sure to hit at least a handful of the great restaurants, cafes, and outdoor spots that we mention below. But first thing is first, start perusing our great collection of rentals now.


Popular attractions and activities

We don't say this lightly considering just how diverse and beautiful virtually every place on Cape Cod is, but: this Outer Cape town has an amazing array outdoor attractions. It's almost impossible to define all of them so we'll list some starting points here, but feel free to ask us for more advice:

- Marconi Beach: You know that image of a beach with a natural looking panels of wood loosely strung together dancing in the wind and sun over a golden sand beach? Yeah, you're gonna love this beach.
- The Massachusetts Audubon Wellfleet Bay Wildlife Sanctuary: This is a great day trip for families and singles alike featuring a narrow boardwalk and five miles of trails spanning woodlands, beach, and salt marshes. Don't miss the aquarium and educational content if you go.
- Atlantic White Cedar Swamp Trail - Another spot on the CC National Seashore that spirals around through the wods near the Marconi Wireless Station. A can't skip for hikers and naturing loving vacationers.
- Jeremy's Point: If you book a vacation rental here, be sure to rent a boat or hire one to take you out to this remote beach located at the very end of Great Island. Its wildlife and truly remote and pristine shores will wow you.
- White Crest Beach: sand dunes abound this amazing Wellfleet beach on the north side of Marconi Beach. It's less populated than most of the National Seashore beaches -- good for you introverts.
- Uncle Tim's Bridge: if you're staying in a Wellfleet cottage or house near Main Street/town center and want to be in nature in short order, then you can walk over to this boarded walking bridge that jets out over Duck Creek. It's a low-lying bridge built in 1783, originally.

What's the bottom line?

Nature and the outdoors have been a big, big draw for this community and annual summer visitors so you really can't go wrong.

In addition to its natural beauty, there are cultural and historical attractions that travelers staying in a vacation rental in Wellfleet (or nearby) won't want to miss. Its town center and surrounding areas have many art galleries featuring local artists (many of whom are year-round residents). We like the Frying Pan Gallery with paintings and mixed material arts inside and the beach and ice cream across the way. But there are many gallery options walkable from town. Wellfleet Preservation Hall is a beautiful building and will surprise you that it's in such a quaint town. It has open mic every Wednesday and is a popular event spot, too. Keep an eye on the calendar if your cottage rental is in town.


Annual events

The annual Wellfleet OysterFest is put on by Wellfleet SPAT. It's a great celebration and family-oriented festival in the town center. OysterFest is always on a weekend and it celebrates the town's renowned oysters, shell fisherman, culture and traditions. You can buy oysters, look at art, or participate in the silent auction. In our opinion, the most unique and can't-miss part of OysterFest is the "shuck off" where, you guessed it, oysters are shucked in a fun competition. It has been going on for 20 years so add this to your list, for sure.

Perhaps super niche and with not quite so much fanfare, there is an annual Wellfleet Road Race for your runners out there. It usually starts near Mayo Beach and is known to be a gorgeous trek along Wellfleet Harbor.

Ok, maybe this isn't quite an annual event, but big shout to The Beachcomber which has been an institution for 42 years and running! Plus the view atop Cahoon Hollow Beach is regularly cited in national publications and magazines as a country-wide landmark. More below...check it out.


Great restaurants and food

There are only a few towns on the Cape that can claim to have restaurants and a food scene that is on-par with the some of the best cities and areas in the country. Wellfleet is one of them.

If you're in the mood for a classic and unique beach-side dining and entertainment, check out the Beachcomber. Chances are, you've seen the Beachcomber's bumperstickers on cars and sweatshirts around the Cape. It won't take long for you to see why when you approach the venue which sits on a beach bluff high atop Cahoon Hollow Beach. There's music, a lively bar, and great fried seafood options to go with the view. Singles and partygoers take over around dinner time so be mindful of when you arrive.

The beachcomber isn't the only restaurant on the water that merits mentioning. The west side of the town is where many Wellfleet vacation rental options are and that's also where you'll find Mac's Shack and Mac's On The Pier -- both offer amazing seafood options but with very different dining experiences. Mac's Shack has a bar with a decent social scene (by Cape Cod standards!) so you can get some wild cocktails and even sushi. While Mac's On The Pier in Wellfleet is a super casual "clam shack" directly on Wellfleet Harbor.

To be honest, there are just too many worthy food options in Wellfleet and not enough space! We'd be remiss if we didn't recommend trying Pearl Restaurant for some family-friendly classic seafood, PB Boulangerie Bistro for a fine French dinner and bakery (you can't miss with their bakery!), and the sneaky good, best-kept-secret Flying Fish Cafe, which has some outdoor seating for a great breakfast and brunch experience. We could go on but we're out of space!


Unique Wellfleet vacation rentals on Cape Cod Vacation Rentals

Perhaps like no other place, when you find that perfect, unique rental in the right part of Wellfleet on CapeCodVacationRenals.com, the stars align! We have outstanding options for a one-of-a-kind stay in this haven. Our team can answer any questions you have about your Wellfleet vacation. Find your vacation rental and inquire today!