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Luxury Vacation Rentals in Wellfleet

(15 rentals)
Wellfleet Cottage
Sleeps 16, 5 bedrooms, 2.5 bathrooms
6 reviews

Distance to beach: 10 feet to Mayo

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 1850's in Truro and moved to 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...

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Featured review

"The quintessential, rustic cape codder."

This historical, family cottage provides a wonderful home base for any large crowd and for a wonderful Cape Cod experience. This is a family-run cottage so you may not get all the amenities expected such...

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$866
avg per night
Wellfleet House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Distance to beach: 1 miles to Gull Pond

Key Amenities

  • Kid friendly

About this property

This beautiful contemporary Cape has all the right ingredients to make your stay a memorable experience. Located just steps away from the Wellfleet woods, there are plenty of trails to walk and Gull Pond is just about 1 mile away. Inside we have a first floor master with full bath. Laundry on the first...

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$714
avg per night
Eastham House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

A 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 the heater). Modern and beautiful kitchen with every amenity. A kitchen island that can sit four people and a dining room...

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Featured review

"Wonderful stay"

Our family of 9 recently stayed at Stephanie’s vacation home and had a wonderful time. The home is exceptionally clean, well organized and comfortable. Stephanie has made this home very thoughtful for...

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$857
avg per night
Eastham House
Sleeps 12, 5 bedrooms, 2.5 bathrooms
1 review

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

Key Amenities

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

About this property

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 multi-family summer retreat. There are plenty of private living spaces for parents, kids & grandparents...

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Featured review

"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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$741
avg per night
Eastham House
Sleeps 7, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 1 miles to Coast Guard

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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Featured review

"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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$714
avg per night

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Eastham House
Sleeps 10, 5 bedrooms, 3 bathrooms

Distance to beach: 1 miles to Boatmeadow

Key Amenities

  • Kid friendly

About this property

HEATED POOL! Wonderful and spacious 5-bedroom home located in a lovely Boat Meadow neighborhood offering in-ground heated pool and association tennis and pickle ball courts. Two of the bedrooms have queen beds, one on the ground floor, the other upstairs; the other bedrooms (all upstairs) have twins....

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$714
avg per night
Eastham House
Sleeps 10, 5 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Kid friendly

About this property

This custom beach house on the bay was built for comfortable family beach front living and entertaining. The main 4-bedroom/3.5-bath house sleeps 9 (up to 12 when combined with the guest suite over the garage), making it ideal for large multi-generational family groups. The home faces due west for great...

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Featured review

"Perfect in every way!"

Our family has been coming to Eastham for decades and this house was the best stay ever! On a private beach, every room has an amazing view and the owners are most generous with amenities. We like to...

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$1,905
avg per night
Orleans House
Sleeps 10, 5 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Skaket Beach

Key Amenities

  • Kid friendly

About this property

Suitable for 2 families or extended family. 2 Kitchens, 2 entrances. Sleeps 10.

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$929
avg per night
Orleans House
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

  • Kid friendly
  • Private pool

About this property

With multiple separate entry points this property is perfect for larger or multi-generational groups. Each home has private entries and are connected by a covered walkway. Enter the front home into the living/dining area with kitchenette. Queen bedroom 1 is accessible from the front entry and has a private...

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$1,495
avg per night
Orleans Condo
Sleeps 10, 5 bedrooms, 3 bathrooms

Key Amenities

  • Kid friendly

About this property

Let nature surround you in this sprawling contemporary where an artists touch and peeks of the Atlantic Ocean are present throughout. Enter this home into the large living, dining space with vaulted ceilings & large sliders all around. Down the hall from the living area you will find a full bath with...

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$975
avg per night
Orleans Condo
Sleeps 10, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Kid friendly
  • Private pool

About this property

Smell the sea air and listen to the soothing rhythm of the ocean at Sea Mist! A short 2/10ths of a mile from one of the most beautiful beaches on Cape Cod, this property brings together easy access to Nauset Beach with the luxury of a salt-water heated pool that includes a hot tub and sun shelf. Inside,...

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Featured review

"Great for large families"

We loved our time in this beautiful home! The pool and spa were an added bonus. We had three families of our extended family together and there was plenty of room for everyone to spread out and have their...

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$956
avg per night
Orleans House
Sleeps 11, 5 bedrooms, 3.5 bathrooms

Distance to beach: 1 miles to Nauset

Key Amenities

  • Kid friendly

About this property

Cape Cod elegance describes this expansive, fully air-conditioned home sitting peacefully on 2.4 acres in the desirable Pochet area of East Orleans. Beautifully renovated in 2022 with new furnishings throughout makes this 5 bedroom, 3.5 bath home ideal for the larger gathering. The open kitchen/dining/living...

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$700
avg per night
Orleans House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Kid friendly

About this property

This beautiful 3 bedroom 2.5 bathroom Crystal Lake home has high end finishes throughout and a location that can't be beat! Crystal Lake Haven has peeks of Crystal Lake and direct access to the lake via the property in front of it. The main level offers a large eat in kitchen/living area with...

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$750
avg per night
Brewster House
Sleeps 10, 5 bedrooms, 5 bathrooms

Distance to beach: 0.0 miles to Breakwater

Key Amenities

  • Kid friendly

About this property

WATERFRONT on Cape Cod Bay! This exceptional beachfront property offers direct access to the private, sandy shores of Breakwater Beach via a private stairway — your own gateway to the stunning coastline. Spanning three air-conditioned levels, this spacious and beautifully appointed home is perfect...

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$1,929
avg per night
Brewster Estate
Sleeps 16, 6 bedrooms, 3.5 bathrooms
3 reviews

Distance to beach: 2 feet to on property

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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Featured review

"Perfect family vacation spot"

This property is the perfect place for a family vacation. It is situated right on a pond that offers fishing and kayaking. You are also only a 5-10 minute ride to a number of beaches. There is also plenty...

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$1,500
avg per night
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