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 a beautiful scene of the sun setting in the far west on the patio just below the wrap-around porch. Avoid the hassle of driving to crowded beaches by walking down the steps to the private Mayo Beach below and bask in the afternoon sun.
This cottage features a newly renovated eat-in kitchen, terrific for hosting a New England clam bake for the whole family. The private master bedroom suite with new tiled full bath is perfect for in-laws that want a quiet get away and a window air conditioner unit. The sleeping porch features two sets of bunk beds; plenty of room to invite cousins and friends. Many game nights have been played in the spacious living room. Upstairs you will find 3 comfortable bedrooms with all new Sealy Posturepedic mattresses, two with queens and one with a set of twins. There is also a sleeping nook at the top of the stairs for extra guests with a terrific view of the harbor. Bring your boats and moor them out front or bring your kayaks and leave them on the seawall. Wellfleet has something for everyone: nearby is golf, tennis, sailing lessons, fishing, fresh water ponds, ocean beaches, birding, hiking and art galleries. This is a trip that you, your family, and your friends will remember for a lifetime.
Unique Benefits
Waterview from almost every room. 1/2 mile to golf, tennis, pickleball, galleries and fresh oysters and clams.
Why Kids Love It
Walk to sandy beach and warm gentle waters.
Playground and pickleball.
Bookstore, and Wicked Oyster
Spectacle Pond
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Aug 14 - Aug 27 2026 | $12,500 | 7 nights | |||
Aug 23 - Aug 30 2026 | $1,785 | $2,500 | $12,000 | 5 nights | |
Sep 07 - Sep 14 2026 | $7,500 | 7 nights | |||
Sep 21 - Sep 28 2026 | $7,000 | 7 nights | |||
Sep 25 - Oct 02 2026 | $7,000 | 7 nights |
Fees:
Last updated on June 27, 2026
Richard S.Exactly
This is a beautiful house in a perfect location. It was exactly what our family needed. The owners were attentive and friendly. Fantastic place. Would return in a heartbeat.
Stayed: May 2026 Submitted: June 07, 2026
Host response
"Richard,Glad you had a wonderful family celebration. Cheers to you Mom!Love to have you backThe Cuttings"
Lovely old Cape House with amazing view
My family really enjoyed staying here. The house has a beautiful wrap around porch with an amazing view you can enjoy. Private but also so close to the Wellfleet waterfront.
Stayed: June 2025 Submitted: July 02, 2025
Host response
"Hi Lynn,Glad to have your family as our guest.Robert"
Quintessential Old Time Cape Home
One of our daughters was getting married a the Chequessett Club right down the road from this cottage. Stepping into the cottage was like going back to an earlier time period. The knotty pine walls and summer cottage feel was great. The view from the wrap around porch never got old from sunrise to sunset there was always something to see out on the water. We had a toddler staying with us; having quick beach access all day long was a plus for our family. We loved the private Mayo beach, especially with a little one. The large kitchen was great for preparing meals or just hanging out together around the table or being together in the living room and the hammock on the porch was well used while we were there. It is hard to find a pet friendly rental, but we were able to bring our 3 family dogs with us without an issue. The dogs also loved the beach and the porch as well.It was also a wonderful place to take bridal photos before the ceremony, the back drop of the water was amazing as well as the wrap around porch.We made many memories for the time we stayed at Morningside.
Stayed: September 2024 Submitted: October 22, 2024
Nancy N.Phenomenally relaxing time!
We stayed at this Wellfleet cottage for a week in mid-September. Despite torrential rain when we arrived, and not the sunniest weather, we had a phenomenal time. This is an old timey, rustic "cottage" (in quotes because it is quite large) that I wish I had spent my summers at as a kid. Four adults (5 for two nights) and two dogs and we had plenty of space. Sitting on the porch drinking tea listening to the waves crash - even in the rain - was amazing. Don't be intimidated by the stairs - they are sturdy, easy, and my elderly German Shepherd had not difficult with them after swimming and running on the beach that is literally at your doorstep. Lots of long walks on the beach, around town, and off-road. Plenty of places to eat - lots within walking distance so bring a headlamp to walk home after dinner out! Pickle ball and basketball courts down the road. We found a breakfast place to walk to and get our morning walk in that had outdoor seating that welcomed dogs. We swam. Played games. Relaxed. Explored which you can do with or without a car. Best of all, the Cuttings were extremely easy to work with. Very communicative. Even called the 2nd day to make sure everything was as it should be. That is terrific service and, unfortunately, not that common. If you are looking for a place that you and your kids can be kids and not worry about walking around in a wet bathing suit, this is the place for you!
Stayed: September 2024 Submitted: October 04, 2024
Host response
"Thanks, Nancy, for the 5 Star review. Looking forward to having you back and hopefully the weather will cooperate.Take Care The Cutting's"
Classic summer week at the Cape!
If you are nostalgic for that cottage by the sea – the one perched up on a bluff with an expansive porch (oh that view!), wooden & wicker rockers, creaky screen doors, white shiplap walls and ceilings in the upstairs bedrooms, this place is for you. Owned by the same family for decades, upon arrival it immediately feels as if YOUR family has owned it for generations. This is a family place for those summers of yesteryear, and that feeling can be captured if you stay here. Laid back and comfortable, it has a worn-in feel, not fussy. Dip your feet in the pail to rinse the sand off and settle inside for board games, movies, cards. There’s enough room for everyone to find their space. The functional kitchen leaves ample room for dining and getting around each other in the chaos of a family meal. Salty breezes coming directly off the bay will rattle the old windows in the eaves, and even that sound gets tucked into your memories. For this is a special memory-making place. One for people who love to be around their family (you can hear through the walls and that is exactly part of its charm), saying good night by hollering to each other never gets old and laughter abounds. We want to thank the Cutting family for keeping the OLD CAPE vibe alive and for sharing it with us! We can’t wait to get back on that porch to experience magnificent sunsets, watching the oyster people work at low tide and the special camaraderie and conversation that only a magical place like this can inspire. So classic is this house that it appears in one of Edward Hopper’s paintings. It is sure to become one of your classics too.
Stayed: September 2022 Submitted: March 14, 2024
Host response
"Thanks for the 5 star review. Looking forward to having you back on the Bluff!"
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