Wellfleet Rentals by Owner

(31 rentals)
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Key Amenities

  • Oceanfront
  • Pet friendly
  • Rentals by owner

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

"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 ...

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5 BR | 2.5 BA | Sleeps 16 | Quick View

3

Distance to beach: 10 feet to Mayo

$852

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Rentals by owner

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. ...

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Property Type

Wellfleet Cottage

"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 ...

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Private end unit in a small cottage community. Two bedrooms (1 double bed, 3 twin beds); pleasant sitting room; kitchen area; porch with table for dining and wooded view. Heating/air conditioning units. Charcoal grill. Comfortable and fully equipped, including dishes, utensils, coffee maker, microwave, ...

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Property Type

Wellfleet Cottage

"Love this place"

I love the homey feel of the cottage, the woods out back, the Wellfleet C of C guide covers hanging on the walls. I'll be staying a week in both June and Sept. this year as I can't get enough of Wellfleet ...

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

This upscale home is located in a quiet child-friendly neighborhood with easy access to private beaches near Indian Neck Beach. Do you prefer a longer hike? Check the tide, and walk via the shoreline to village shopping, art galleries, and restaurants in downtown Wellfleet!You will instantly feel ...

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Property Type

Wellfleet House

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3 BR | 1 BA | Sleeps 5 | Quick View

2

Distance to beach: 1 miles to South Sunken Meadow Beach (Bay side)

$254

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Located on 1-acre lot on quiet lane .Sorry no pets allowed on the property.Beach Pass Included. FREE USE of a Surfboard, 2 Standup Paddle Boards (with an Adjustable Paddles and Leashs)!!! 4 Bicycles 6 Bodyboards Beach Chairs Umbrellas Outside Gas Grill Weber Charcoal Grill WI-FI Cable ...

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Property Type

Eastham Cottage

"A little gem"

While searching for a cottage, I stumbled across a wonderful place off the main roads and wow… What a gem! The location was perfect, five minutes to several beaches on the Bayside, and only seven minutes ...

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Summer 2025 Season: Saturday Changeover in June and July, Sunday Changeover in August into September, 7 night minimum stayA brand new 4 bedroom w/ private bonus room (pull out couch), 3 full bathrooms, recently remodeled in Spring 2023! HEATED POOL (pool is in direct sun and will stay warm even without ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 2 miles to Coast Guard and Nauset Light Beach

$452

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Indulge in luxury during your vacation at this impeccably renovated house. Pristine and tastefully decorated, it boasts central air conditioning with mini splits in each room, stunning hardwood flooring throughout, and a gourmet kitchen equipped with soapstone countertops, high-end appliances, including ...

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Property Type

Eastham House

"Wonderful child-friendly home in a great location."

The location is fantastic - close to many restaurants and beaches in Orleans, Eastham, and Wellfleet. It's also a 30 second walk from the front door to the Cape Cod Rail Trail. The house has a nice, modern ...

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Relax with the whole family at our beautiful 4BR/ 2 BA cottage in located just off the route 6, in a quiet cul-de-sac setting. House is equidistant from both bay and ocean side beaches, and less than 1.5 mile from the nearest beach. It is minutes away from the bike trail, drive-in movie theater, mini-golf ...

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Property Type

Eastham House

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Key Amenities

  • Rentals by owner

About this property

****PLEASE NOTE: BECAUSE OUR HOME IS ALSO UTILIZED DURING THE SEASON BY SEVERAL FAMILY MEMBERS AND IN ORDER TO ACCOMMODATE THEIR SCHEDULES , WE DO NOT ACCEPT ANY RESERVATIONS EARLIER THAN JANUARY OF EACH RENTAL SEASON. (i.e. JANUARY 2024 FOR SUMMER OF 2024)***Unique rental changeover (Friday to Friday) ...

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Property Type

Eastham House

"Comfortable, Quiet, Convenient and Classy"

Dear John,We really enjoyed staying at your home on the Cape. We loved how quiet the neighborhood was and how close the house is the the rail trail (and Mac's Seafood!). The house was well stocked, ...

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Key Amenities

  • Rentals by owner

About this property

Nestled on quiet street, in a peaceful bayside neighborhood, beautifully renovated and appointed 3 Bedroom 1.5 Bath, with an enclosed outdoor shower. This pristine one-level cottage is now booking year round vacations! All new furnishings, beds and appliances!Featuring central AC, sliders to back ...

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Property Type

Eastham House

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Key Amenities

  • Rentals by owner

About this property

Private cul-de-sac 1 mile from beautiful Nauset Light Beach, 1.5 miles from Coast Guard Beach, one of the top 10 beaches in the USA year after year.Google THE BEST BEACH TOWN IN MA according to Stacker.Easy walk or bike ride to the beach.Wellfleet and Truro are nearby; 25 minutes to Provincetown.Near ...

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Property Type

Eastham House

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2 BR | 1 BA | Sleeps 4 | Quick View

owner special
Owner special: 20% discount if book before May 1st!

Distance to beach: 0.5 miles to Thumpertown

$375

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Set among cool pine trees, quiet and private, this cute cozy cottage is 1/2 mile walk to Thumpertown Beach on Cape Cod Bay. Come and have an old-style Cape vacation in air conditioned comfort and bring your family pet!This property has been rented on another site for many years and always had fantastic ...

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Property Type

Eastham Cottage

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5 BR | 2.5 BA | Sleeps 12 | Quick View

1

Distance to beach: 2 miles to Coast Guard Beach National Seashore

$1133

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

JULY & AUGUST ARE BOOKED, BUT WE STILL HAVE JUNE & SEPTEMBER WEEKS AVAILABLE WITH A HEATED POOL!! ASK ABOUT OUR PROVINCETOWN THEME WEEK AND WELFLEET OYSTERFEST SPECIALS!! Spend the day at the National Seashore then come home for an evening swim in a heated pool. This home is perfect for a ...

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Property Type

Eastham House

"Great House!"

Very close to Coast Guard Beach. Grandkids biked each day, while the "elders" stayed poolside. Lots of room for everyone, including our two dogs. The welcome package was a nice touch.

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3 BR | 2 BA | Sleeps 7 | Quick View

3

Distance to beach: 1 miles to Coast Guard

$698

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Our home has three spacious bedrooms, all on one main floor. The primary bedroom has a king-sized bed and a gorgeous waterfront view. The second bedroom has a queen and twin-sized bed, and the third bedroom has a queen-size bed and water view with access to an outside deck and outdoor shower. All beds ...

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Property Type

Eastham House

"Fabulous Family Vacation!"

We spent the week with our adult sons and their partners and had a great time. The weather was less than we expected for July- only in the 70s, but the house made being there wonderful anyway. The view ...

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3 BR | 2 BA | Sleeps 6 | Quick View

4
owner special
Owner special: Weeks starting at just $2500. !!

$472

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Beautiful home is located at the end of a culdesac in a lovely neighborhood. Huge deck overlooks the Cape Cod Bike Trail. Includes large outdoor shower, 3 tvs and AC for each room. Use of 2 Association tennis and pickle ball courts is included. as well as 2 kayaks. Newer Kitchen with all amenities is ...

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Property Type

Eastham House

"Beautiful home great location"

This home was perfect for our of summer family vacation House is spacious and sits right by the Cape Cod rail trail which our dog loved Rental included access to pickle ball courts which my kids loved ...

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4 BR | 3.5 BA | Sleeps 8 | Quick View

Distance to beach: 75 yards to TOWN COVE

$1357

avg/night

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Key Amenities

  • Kid friendly
  • Private pool
  • Rentals by owner

About this property

MODERN UPDATED AIR CONDITIONED HOME ON TOWN COVE, FEATURING LARGE IN GROUND HEATED POOL WITH AIR CONDITIONED POOL HOUSE AND OUTDOOR KITCHEN W/ APPLIANCES. HOME CONSISTS OF PROFESSIONAL GAME ROOM FEATURING PROFESSIONAL POOL TABLE, CARD TABLE, WITH PRIVATE BAR AND TV ROOM, PING PONG TABLE AND CORN HOLE. ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 6 | Quick View

4
owner special
Owner special: Walk to July 4th fireworks! Special on week of 6/28-7/5: $4000. Please inquire.

Distance to beach: 0.0 miles to Bay

$488

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Costal gem! Secluded, quiet 3 BR house on 3 acres.Great for wedding guests, family vacations, golf weekends, girls weekends, or a mid week escape! Yes we have a pack & play for little visitors! Updated house with all amenities. Bay beach is .03 miles up the road. Private basketball court ...

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Property Type

Eastham House

"Fabulous! Best July 4th at best house!"

Fantastic house, everything we need, loved the grill, pristine kitchen. Beautiful back yard, kids loved the basketball court. Walked to fireworks up the road at the beach, gorgeous night. We took in the ...

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

THE VIEW AND BEACH DON'T GET ANY BETTER THAN THIS. Charming two story two bath fisherman's cottage with historic charm -- white-washed beamed ceiling, and antique claw foot tub, marble sink. Second floor living room has 14 feet of glass looking doors looking out over the water. Fireplace ...

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Property Type

Truro Cottage

"Beyond your wildest dreams"

Jil was incredibly friendly and helpful with answering our questions and booking. My wife and I are very familiar with this part of Cape Cod but were absolutely blown away by the privacy and natural beauty. ...

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

Our waterfront cottage and attached barn are perched atop the dramatic coastal bluff along Cape Cod Bay with stairs down to our private beach. We have two cottages and a barn on this acre of waterfront land, plus our own staircase down to the private sandy beach.This rental consists of a two-story ...

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Property Type

Truro Cottage

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3 BR | 1 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.0 miles to Cape Cod Bay

$724

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

Our charming 3-bedroom cottage is perched atop a dramatic bluff on a waterfront acre of land, offering a spectacular, unobstructed view of Cape Cod Bay and the entire “arm” of the Cape, from Provincetown to Plymouth. Beach stairs take you down to your own private beach. At high and low tide, ...

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Property Type

Truro Cottage

"A beautiful summer experience"

An old world Cape Cod treasure. Splendorous views, private beach access, quiet and private. A very special cottage.

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3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 200 yards to Private Deeded Access

$775

avg/night

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Key Amenities

  • Beachfront
  • Rentals by owner

About this property

Bluestar Bluff is a bright, contemporary home with expansive Cape Cod Bay views and deeded beach rights across the street, is the perfect place for a vacation.Designed to maximize views, the house is upside down. The upstairs is an expansive loft-like great room, flooded with natural light from oversized ...

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Property Type

Truro House

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2 BR | 1 BA | Sleeps 4 | Quick View

$343

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Rentals by owner

About this property

Enjoy breathtaking sunsets over Cape Cod Bay from this private, direct beachfront rental on kid-friendly, Skaket Beach in Orleans. Charming 2nd floor apartment with stunning views. Living area, 2 bedrooms, 1 bath and kitchenette. Very clean, cozy & simple. Max 4 people. Sorry no pets allowed.

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Property Type

Orleans Apartment

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4 BR | 3 BA | Sleeps 9 | Quick View

3

Distance to beach: 0.9 miles to Nauset Beach

$482

avg/night

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Key Amenities

  • Rentals by owner

About this property

Escape to our spacious four-bedroom home in East Orleans, just minutes from Cape Cod’s stunning beaches, including Nauset Beach and the Cape Cod National Seashore. Perfect for relaxation or adventure, this coastal retreat has everything you need for a memorable stay.Enjoy modern comforts with ...

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Property Type

Orleans House

"**Would Rent from Nina Again!**"

This house has a fantastic location, just a short stroll (less than a mile) from Nauset Beach - one of our favorite beaches on the Cape. It's modern, elegantly decorated, and thoughtfully prepared for guests. ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$375

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Beautiful summer rental close to shopping, tennis courts, playground and bike trail. Short drive to bay side beaches and ocean. All the amenities of home. Linens and Towels are provided.

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Spacious 2,500 square ft. family home with abundant natural light nestled in a private association of 20 homes in easy walking distance (0.3 miles) to a saltwater pond (Meetinghouse Pod). Our house is on a 0.7 acre lot with a large, wooded backyard offering privacy in a neighborhood surrounded by Pleasant ...

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Property Type

Orleans House

"Great stay"

Our family (3 adults, 2 kids) had a wonderful week in this lovely home! The location offers plenty of privacy and space in a quiet neighborhood. The house was airy and clean, and the kitchen had pans, serving ...

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Key Amenities

  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

This beautiful, sunny farmhouse located near the heart of Orleans is an antique home that has modern updates inside and a gorgeous surrounding yard. Very private with ample parking. Walking path to Gould Pond for birdwatching and nature walks.The house is open, airy, very clean and well cared for. ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

ONLY TWO WEEKS LEFT IN July 5 - 12th & July 12th - 19th 3 NIGHT MIN IN JUNERecently Renovated 3/1 with new kitchen & bath & close to beach w Central ACThis cozy, recently renovated cottage has a brand-new kitchen, new bathroom, and new flooring and is an excellent location, close ...

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Property Type

Brewster House

"A Restful Piece of Paradise !"

There aren't enough accolades in a dictionary to describe Shannon OR this Cape Cod cottage! Open the front door and you can't help but say "WOW!" Then walk through the three bedrooms and you'll note that ...

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1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.1 miles to Herring Cove

$481

avg/night

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Key Amenities

  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Panoramic water views, short walk to Herring Cove in front of us and, to the left, a four minute walk to the Harbor Beach at Provincetown Inn and the jetty over to Long Point. Overlooking Hatch's Harbor in Cape Cod National Seashore, at the tip of Provincetown.From this PEACEFUL PANORAMIC PERCH, ...

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Property Type

Provincetown Condo

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4 BR | 3 BA | Sleeps 8 | Quick View

$450

avg/night

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Key Amenities

  • Rentals by owner

About this property

4 bedroom 3 bath house in quiet neighborhood ..Large living room,central air and screened in porch and large deck with view of the lake. Beach is only a few steps away.

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Property Type

Brewster House

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6 BR | 3.5 BA | Sleeps 16 | Quick View

Distance to beach: 2 feet to on property

$1589

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

We've been told pictures can't capture the beauty of this home and location. The view is breathtaking and the solitude is welcoming. The kitchen has everything you need to make incredible meals. The beds are heavenly with feather pillows and 400 thread count linens.In the kitchen and laundry ...

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Property Type

Brewster Estate

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Please call for pictures and more info- owners are private and appreciate screening first to see if a fit large gorgeous newly renovated home sleeps 11 3 floors with finished walkout basement with games and sitting and playing including air hockey 5 bdr 3 full baths; a queen and twin on first floor ...

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Property Type

Chatham House

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Wellfleet Vacation Rentals