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Luxury Vacation Rentals in Eastham

(22 rentals)
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 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
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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$714
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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$714
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

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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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$725
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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$944
avg per night
Wellfleet House
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews

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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Featured review

"Perfect family Wellfleet rental"

Our family has been vacationing in Wellfleet rental properties for decades. Irena’s home has been the best to date by far. The peaceful location and view of the inlet are perfect for outdoor relaxation...

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$729
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
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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$875
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
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
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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$1,400
avg per night
Harwich House
Sleeps 10, 5 bedrooms, 2.5 bathrooms
1 review

Distance to beach: 2 miles to Bank Street Beach

Key Amenities

  • Kid friendly
  • Private pool

About this property

Experience Cape Cod at this stunning 5 bedroom Harwich home with heated pool, gorgeous yard and the perfect Cape Cod charm.This home is ideally located within just 450 ft. from the Cape Cod Bike Trail, a great park in Brooks Park with Tennis and Pickleball courts as well as where the Harwich Mariners...

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Featured review

"Absolutely perfect home"

Just spent a week at this gorgeous home and cannot say enough about it. The property is quiet and private, beautifully landscaped with gorgeous trees and flowers, and lots of easy parking. The location...

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$929
avg per night
Chatham Estate
Sleeps 19, 9 bedrooms, 3.5 bathrooms
4 reviews

Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

This family estate was built in the 1930's by Mr. & Mrs. John Peale Bishop, a famous writer and poet and best friends of the infamous F. Scott and Zelda Fitzgerald, and is nestled on 1.3 acres overlooking the beautiful salt marshes and the ocean! It is ideal for family reunions, vacations, girl...

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Featured review

"Amazing house"

We celebrated my Mom’s 80th birthday with our family at the Gatsby home. It was a perfect house to celebrate with the whole family. The grounds are breathtaking and you can walk to the beach. The caretaker...

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$1,143
avg per night
Harwich House
Sleeps 10, 4 bedrooms, 3.5 bathrooms

Distance to beach: 2 miles to Bank Street Beach

Key Amenities

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

About this property

Welcome to the Harwich Haven! This 4-bed, 3.5-bath retreat in Harwich, MA offers a spacious family room, modern kitchen, swimming pool, fire pit, two decks with outdoor dining, an outdoor grill, private fenced in yard, two newly renovated ensuite bathrooms with spa amenities and more. With easy access...

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$1,000
avg per night
Harwich House
Sleeps 14, 9 bedrooms, 6.5 bathrooms

Key Amenities

  • Kid friendly

About this property

Harwich Port- Welcome to CapeCodProperty 198, a luxurious retreat nestled in the charming Harwich Port, just walking distance to Red River Beach. This expansive 9-bedroom, 6.5-bathroom home is perfect for large families or groups, accommodating up to 14 guests in comfort and style. As you step inside,...

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$1,100
avg per night
Harwich House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 0.1 miles to Atlantic Street Beach

Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Welcome to your perfect Cape Cod getaway! Location, location, location. Nestled on a quiet, private dead-end lane in the highly sought-after Campgrounds neighborhood, our beautifully appointed vacation home is just a 3-minute stroll to the warm waters of Nantucket Sound beaches (without crossing Route...

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Featured review

"Vacation Perfection"

I highly recommend this outstanding vacation home for anyone looking for a perfect stay in a fantastic location. This wonderful house is a short walk to both beach and town and an easy car ride to two...

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$1,000
avg per night
Dennis House
Sleeps 11, 4 bedrooms, 2.5 bathrooms
1 review

Distance to beach: 10 miles to Many many beaches

Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront
  • Rentals by owner

About this property

Large 4 bedroom colonial on a private salt water beach with walkout basement, outdoor shower and lower level play rooms for the youngsters. Morden kitchen with big center island. Formal dining room, huge living room, large family room, pantry & private office.Mordern baths with an outdoor shower....

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Featured review

"Could Not Have Been Better! Wonderful stay!"

Our family of 11 ( 8 adults and 3 children, ages 6-10) had a wonderful time in this spacious home. We kayaked ( one double and 3 single kayaks were provided), swam in the lake, biked or jogged on the nearby...

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$1,143
avg per night
Dennis House
Sleeps 15, 7 bedrooms, 3.5 bathrooms

Key Amenities

  • Kid friendly
  • Private pool

About this property

This new rental was purchased with your family get together in mind. The owners wanted to give you an opportunity to have a place to gather with friends and family and either host a special event or just social distance with loved ones in a beautiful serene atmosphere. Whether its in the spacious house...

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$900
avg per night
Dennis House
Sleeps 14, 6 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Kid friendly
  • Pet friendly
  • Private pool

About this property

Discover a luxurious stay at this stunning Dennis vacation rental, perfectly situated just a short walk from the beach. This 6-bedroom haven 9 (ALL with en-suite bathrooms) is designed to accommodate up to 14 guests, making it an ideal retreat for large families or groups looking to create unforgettable...

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Featured review

"Our Best Cape Cod Stay!"

We had an absolutely amazing stay at this beautiful Cape Cod home! Our family has been coming to Cape Cod every summer for more than 30 years, and we can honestly say this was by far the best house we have...

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$1,094
avg per night
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