Luxury Vacation Rentals in Brewster

(96 rentals)
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3 BR | 2 BA | Sleeps 8 | Quick View

1

$402

avg/night

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Key Amenities

  • Kid friendly

About this property

Enjoy your Cape escape at this immaculate and remodeled 3 Bedroom 2 Bath home with three finished levels in the popular Brewster Seaview Community. Neighborhood amenities include direct access to the Cape Cod Rail Trail, a tennis court, shuffle board court, picnic area and a Little Free Library. Just ...

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Property Type

Brewster House

"Exceptional home away from home"

I stayed with family for about 1 month. The owners/landlords were helpful, friendly and respe ctful of our needs.The location is private, huge yard,great night sky viewing, great bird sightings. Amenities ...

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Recently 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 to the Bay and just 0.9 miles to Saints Landing Beach. Situated on a 1.4 acre wooded ...

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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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8 BR | 4 BA | Sleeps 15 | Quick View

Distance to beach: 0.1 miles to Parkers River Beach

$917

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Discover coastal living at its finest, nestled only 300 yds to the beach & 150 yds to a lobster roll at the Skipper! Built in 2017, this luxurious estate offers a perfect blend of elegance & convenience. Central air. Exquisite interior, hardwood throughout, abundance of natural light featuring ...

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Property Type

Yarmouth House

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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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Property Type

Dennis House

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4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 0.1 miles to Nauset Beach

$800

avg/night

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Key Amenities

  • Kid friendly
  • Pool
  • 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.  ...

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Property Type

Orleans House

"Beautiful House, Would Move in if We Could"

This home was absolutely gorgeous from top to bottom, and we would move here if we could. The larger bedroom on the second floor has fantastic sunrise views, and I can’t think of a better way to wake ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$750

avg/night

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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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Property Type

Orleans House

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6 BR | 4 BA | Sleeps 12 | Quick View

$727

avg/night

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Key Amenities

  • Kid friendly
  • Pool
  • Private pool

About this property

Fabulous two home property with a pool! This unique property is perfect for larger and multi-generational groups with two houses connected by a covered walkway. Gorgeous heated pool and jacuzzi and large patio with stone fireplace provide perfect outdoor living. The property sleeps 12 with 6 bedrooms ...

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Property Type

Orleans House

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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

$714

avg/night

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Key Amenities

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

About this property

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 Mom, Dad, kids & grandparents to spread out after checking out all of the wonders that Cape Cod offers. ...

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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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5 BR | 3.5 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Nauset

$714

avg/night

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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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Property Type

Orleans House

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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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4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to Gull Pond

$679

avg/night

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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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Property Type

Wellfleet House

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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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Property Type

Wellfleet House

"We found the house that accomodated our 3 generation family!!!!"

This beautiful home is spacious, wonderfully cared for, conveniently located and private. The layout allowed for 10 of us -3 family units-to have privacy and quiet. Up and downstairs living areas were ...

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5 BR | 2.5 BA | Sleeps 16 | Quick View

2

Distance to beach: 10 feet to Mayo

$590

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

"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 ...

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Young, like new ''million dollar'' 3500 sq. ft. colonial style home in a quiet, private hillside setting set back from Route 6A in the very sought after area of East Dennis. Water views of Cape Cod Bay and Northside Marina. One mile to the nearby 18 hole golf course, Northside Marina, ...

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Property Type

Dennis House

"So much room!!"

We were so happy to have found this rental. There was so much space and the house offered everything and more that you could expect for a wonderful stay!! Very clean and offered all sheets and towels, beach ...

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3 BR | 2 BA | Sleeps 8 | Quick View

$500

avg/night

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Key Amenities

  • Rentals by owner

About this property

Charming waterfront cottage overlooking Schoolhouse Pond; 1/2 mile to ocean & beach. Beautifully appointed home in private, secluded setting, with fireplaced LR; formal DR, beautiful sunroom w/ Franklin stove. Primary bedroom on first floor. Well equipped kitchen. Amenities include bikes, kayaks, ...

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Property Type

Barnstable Cottage

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4 BR | 3.5 BA | Sleeps 12 | Quick View

1

Distance to beach: 1 miles to Millway Beach

$500

avg/night

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Key Amenities

  • Kid friendly
  • Private pool
  • Rentals by owner

About this property

**WINTER 2024 and SUMMER 2025 now available to book**Nestled in a picturesque location, our newly constructed rental property is the perfect destination for your idyllic summer retreat. Family friendly, this home has everything you need to relax and enjoy all the best Cape Cod has to offer. The fully ...

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Property Type

Barnstable Villa

"Our favorite home on the Cape!"

We have rented "Making Waves" for 2 years now and truly enjoy staying here! From the responsiveness of the owners to the property manager and the homes amenities-we have found a keeper. The house is meticulously ...

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$500

avg/night

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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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Property Type

Wellfleet House

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$486

avg/night

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Key Amenities

  • Kid friendly

About this property

Located right on the shore of beautiful Town Cove in Orleans. This updated home has 3 bedrooms 2 1/2 baths Nicely appointed foyer and living room with expansive saltwater views, leads you to the sunroom, deck and pathway to the water. Games and books fill bookcases and a large flat screen TV sits ready ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

$457

avg/night

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Key Amenities

  • Kid friendly

About this property

Waterfront(!) on Herring Pond, one of Eastham's finest freshwater ponds. Located on a quiet sandy lane and close to the bike trail, this home is a great spot to vacation!

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Property Type

Eastham House

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Key Amenities

  • Pet friendly

About this property

CENTRAL AIR! -This beautifully renovated 4 bedroom home, just .5 mile to the beach has everything you'll need to enjoy summer on the Cape. Pretty Cape decor with plenty of room inside and out! South Middle and Bass River beaches so close by! 2 bedrooms on each side plus upstairs room available for ...

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Property Type

Yarmouth House

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Key Amenities

  • Pet friendly

About this property

Owner special! July 20-27th. $2000 for the week (plus taxes and fees)Central air! Renovated and ready for your summer vacation! Room for the whole group in this 3 bedroom home with two additional guest rooms, new kitchen, dining area with large table, living room with comfy couches. Large deck with outdoor ...

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Property Type

Yarmouth House

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4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 3 miles to

$429

avg/night

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Key Amenities

  • Kid friendly

About this property

Experience the epitome of comfort and convenience in this charming 4-bedroom, 2-bath home located on a peaceful side street near the popular CC Bike Trail. Enjoy the best of indoor-outdoor living with a spacious deck and screened porch, perfect for relaxing or entertaining. Stay cool and comfortable with ...

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Property Type

Eastham House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

3

Distance to beach: 0.1 miles to Atlantic Street Beach

$429

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Now booking 2025 vacations! Highly sought after vacation home in walkable, historic “Campgrounds” on quiet, private dead-end street. Stroll to Nantucket Sound beaches (without crossing Rt. 28 or Lower County. Rd.) as well as the bustling “Port'' for restaurants, ice cream ...

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Property Type

Harwich House

"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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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Welcome to our Beach Retreat, “After Dune Delight”. Our home was purchased and completely renovated in 2021. Tastefully decorated in classic Cape Cod style and appointed with all your beach vacation needs, the house is located in Colonial Acres, a very quiet and safe neighborhood. We are ...

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Property Type

Yarmouth House

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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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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 600 miles to Nauset Light Beach

$429

avg/night

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Key Amenities

  • Kid friendly

About this property

A unique opportunity! Stay in the Lightkeepers house at Nauset Light Beach! Views of the Atlantic ocean from this home. One of the few homes that is truly a walk to the ocean on the Outer Cape. Retaining all the charm and quirkiness of an antique house this home is sure to give you a memorable vacation. ...

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Property Type

Eastham House

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About this property

Beautiful setting directly on Bass River with an optional dock for deep water access. (floating dock chained around pilings, for boats under 24') Stunning views of the river and out towards the ocean. Near West Dennis Yacht Club and West Dennis beach for long walks and fabulous sunsets. Lovely home ...

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Property Type

Dennis House

"Excellent rental"

Great location. Lovely view off the back deck. Very clean house and extremely well supplied. Good living space with the added all-weather porch. Appliances all worked very well. Internet was a bit slow ...

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Key Amenities

  • Kid friendly

About this property

South Yarmouth - This two bedroom cottage with one bath has been tastefully updated for your enjoyment. Rinse off in the outdoor shower after a day at South Middle Beach which is located just one mile away and a short walk to mini golf, ice cream and restaurants. Primary bedroom with queen bed, second ...

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Property Type

Yarmouth Cottage

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$410

avg/night

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Key Amenities

  • Kid friendly

About this property

Lovingly appointed 4 bedroom, 2 bath Eastham home with beautifully updated kitchen is situated just a short drive down a dirt road. Close proximity to National Seashore Beaches -Nauset Light Beach, Coast Guard Beach and just over a mile from the Cape Cod Rail Trail. Enter this comfortable and calming ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

Location, location, location! 60 steps to a sandy ocean beach (Haigis) right across the street. No need to pack the car for the beach, you just have to walk a minute, and you are there! The property consists of 2 separate 3-bedroom homes located on one lot directly across from Haigis Beach. It's ...

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Property Type

Dennis House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Thumpertown Beach

$407

avg/night

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Key Amenities

  • Kid friendly

About this property

Great beach house just steps away from private beach near Thumpertown Beach. Located in a quiet, secluded spot, this home offers a glassed in porch, three decks (along with a peek of the bay), three bedrooms and two baths! Between the living area, porch and decks there is plenty of room for the family ...

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Property Type

Eastham House

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$401

avg/night

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Key Amenities

  • Kid friendly

About this property

Beautifully renovated 4 bedroom, 3 bath home in Eastham close to Cape Cod National Seashore Beaches--Coast Guard Beach and Nauset Light Beach. Just 1 mile to the Cape Cod Rail Trail. Enter the house to a large great room with cathedral ceilings and open floor plan. Large dining table seats 8. Fully stocked ...

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Property Type

Eastham House

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4 BR | 2 BA | Sleeps 8 | Quick View

$400

avg/night

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Key Amenities

  • Kid friendly

About this property

Overlooking Orleans Town Cove and with direct access to the water, this beautifully remodeled home is your perfect Cape Cod vacation retreat! Light and bright, with beautiful hardwood floors and an open floor plan, the main level has a large, fully equipped kitchen with granite counters and breakfast ...

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Property Type

Orleans House

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront

About this property

Located just 2/10th's of a mile from bay-side Skaket Beach is this sweet 3 bedroom, 1 full bath (tub/shower combination) home offering beautiful tidal marsh views and a spacious deck to enjoy the outdoors. With Central A/C, the property is set back at the end of a sandy lane and is close to the Cape ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly

About this property

Dennis - Recently renovated and new to the vacation rental market for the 2023 season this 5 bedroom 2 bath Cape sleeps 9 and is a short drive to all the popular Cape Cod Bay Beaches! The first floor offers a dine in kitchen in addition to a dining room with sliders leading out to the deck, a living room ...

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Property Type

Dennis House

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3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 500 miles to S. Sunken Meadow

$393

avg/night

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Key Amenities

  • Kid friendly

About this property

Completely renovated, updated home with waterviews! This spacious house will give your whole family room to spread out. Walk to a private beach and located on a quiet side road this is the perfect vacation location. This home has the living area, kitchen and dining area (as well as one bedroom) on the ...

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Property Type

Eastham House

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About this property

Popular rental! Fingers area in West Dennis. This 4 Bedroom-2 Full Bath beautiful home has been completely renovated and ready for wonderful Cape Cod memories to be made and it is only .3mi to West Dennis Beach. Living room, spacious kitchen, dining room, and bedrooms on both floors. After a day at ...

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Property Type

Dennis House

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4 BR | 2 BA | Sleeps 6 | Quick View

$373

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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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to

$371

avg/night

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Key Amenities

  • Kid friendly

About this property

Nice large 3 bedroom home on Eastham's Oceanside. Drive or bike to either Coast Guard Beach or Nauset Light beach. Large deck/patio for outdoor living. Central AC keeps you cool in the summer. Separate family room/TV room plus living room. Nice outdoor space and located on a quiet side road.

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Property Type

Eastham House

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5 BR | 3 BA | Sleeps 10 | Quick View

$371

avg/night

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Key Amenities

  • Kid friendly

About this property

Incredible views from this classic cottage. A unique location makes this an ideal home for the naturalist. Resting above the Boat Meadow River allows easy access to the river and Boat Meadow Beach (via kayak or canoe). Commanding views and incredible privacy and seclusion.

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Property Type

Eastham House

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3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Silver Spring Beach

$357

avg/night

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Key Amenities

  • Kid friendly

About this property

Cape style home with central air conditioning on the bayside of Eastham with access to Cooks Brook Beach. Fully equipped kitchen and dining room, family room opening onto the four season porch then out to the deck. First floor master bedroom with queen, TV and full bath with soaking tub and separate shower. ...

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Property Type

Eastham House

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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

"Spectacular family vacation at Windward!"

I had trouble finding just the right spot for my husband’s 75th birthday celebration where we could accommodate his four grown children and his three year old granddaughter as well as ourselves. Windward ...

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4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to Boat Meadow / First Encounter

$357

avg/night

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Key Amenities

  • Kid friendly

About this property

Large 4 bedroom home with spectacular views of Cape Cod Bay from every room in the house including a spacious second level screened in porch. Kitchen and all 3 bathrooms were completely redone in 2012 with granite countertops, new Chrystal cabinets and new stainless steel appliances in the kitchen. Ductless ...

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Property Type

Eastham House

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$357

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly

About this property

Sweet beach house tucked on a sandy lane, just minutes to both Priscilla Landing inlet and Nauset Beach. The home offers three bedrooms with one king and two others each with a queen bed. There is also one and a half baths. There are window A/C's throughout the house for your comfort and electric ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Perfect spot to relax for your fall cape wedding, or just a quiet stay during the capes most beautiful time-the shoulder season!Our family and pet friendly sunny 2100 sq foot 3 bedroom, 2.5 bathroom immaculate home boasts of a quiet lot, newer large fully stocked kitchen, laundry room, relaxing farmers ...

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Property Type

Harwich House

"Spacious, pet-friendly, and close to everything!"

Communication from the host before you even check-in is amazing. If you have never been to Harwich you already feel like you have been coming here for years with her guide that she sends. This was also ...

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About this property

This charming historic Cape is conveniently located on Route 6A in Dennis Village. Just a quick walk to the Cape Playhouse, Cape Theatre, numerous restaurants, shops, and Cape Cod Museum of Art. This beautifully updated and maintained property is a three-bedroom, two bathroom with multiple spots to ...

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Property Type

Dennis House

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Key Amenities

  • Kid friendly

About this property

Close to everything Yarmouth has to offer. Under half a mile to Smugglers/Bass River Beach & Windmill Beach. Bass River Sports World, Ice Cream, and shopping nearby. Short distance to public golf, town parks, and access to bike trail.Central AC! This split-level home offers three large bedrooms ...

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Property Type

Yarmouth 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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Key Amenities

  • Kid friendly

About this property

This Cape Cod home is perfect for the beach lover, boater, kayaker or paddle boarder with proximity to Mill Pond and boating to the outer beach! Beautiful home offers 3 spacious bedrooms and two full baths on two levels. Main level features a sunny living room with gas fireplace and flat screen TV ...

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Property Type

Orleans House

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Cole Rd

$321

avg/night

View Details

Key Amenities

  • Kid friendly

About this property

Make this your Cape Cod Summer Rental. Located near Herring Brook Landing, this cottage is near the end of a cul-de-sac. Quiet location with two beach accesses. Views of bay from bedroom on second floor. Walk from your deck down a path to a private beach or use Cole Road Beach. Third house back from the ...

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Property Type

Eastham House

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