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Luxury Vacation Rentals in Wellfleet

(19 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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$1,006
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
Wellfleet House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly

About this property

Set within the trees and surrounded by the neighborhood wildlife, this charming 4 bedroom, 3.5 bath home has everything one would need for the perfect Cape Cod vacation, including stunning sunset views across the Wellfleet Bay and a gorgeous stretch of private beach that is just a minute walk from the...

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Featured review

"First bayside experience."

This lovely home made my family very happy. Situated beautifully among the trees with a perfect window for sunsets. Expansive deck accommodating 9 of us comfortably. Room for our kids arts and crafts without...

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$715
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

September pool is still open and available after the 7th! $4k per week in SeptemberA 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...

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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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$1,016
avg per night
New
Last Minute Deal
Eastham House
Sleeps 12, 5 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Kid friendly

About this property

Welcome to Eastham Getaway!Be among the first to stay in this brand new 2026 built designer home, situated directly within the Cape Cod National Seashore. A one of a kind luxury retreat, featuring almost 4000 SF of finished space across 5 bedrooms and 3 bathrooms. Plus a private outdoor oasis featuring...

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Featured review

"Eastham getaway"

This brand new house is extremely comfortable, very well appointed and equipped in a quiet neighbourhood moments from one of the best beaches in the cape. Would highly recommend!

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$815
avg per night

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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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$921
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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$741
avg per night
New
Truro House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Experience subtle luxury, warmth and inviting charm. Three bedroom home with a spacious open floor plan set on 1 acre in the hills of North Truro. The upper floor has a wrap-around deck overlooking the beautiful abutting woodland with a patio table, lounge chairs, hammock and BBQ grill. Just off the...

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$700
avg per night
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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$721
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
Truro Cottage
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

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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Featured review

"Best Vacation We’ve Ever had!"

This is our third time staying here and my husband just said to me, “That was the best vacation we’ve ever had.” The cottage strums, the heart strings of classic Cape Cod nostalgia. It is beautifully...

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$736
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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$1,520
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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$1,063
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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$1,134
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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$756
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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$781
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
2 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

"Almost Heaven…."

Our family (of 14) spent a week in this beautiful home at the end of May. It truly is a special place in many ways. The home is comfortable, spacious and has everything you need to feel at home.The...

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$1,500
avg per night
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