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Holiday Homes in Brewster

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157 rentals in Brewster.
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Walk to Beach, Beautiful Brewster Home! Crosby, holiday rental in Brewster

Walk to Beach, Beautiful Brewster Home! Crosby

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Newly Updated Brewster Cottage, 150 feet from Private Beach: 021-B, holiday rental in Brewster

Newly Updated Brewster Cottage, 150 feet from Private Beach: 021-B

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Ocean Edge Luxury Condo,  Constantly Updated, Just steps to Arbor Pool, holiday rental in Brewster

Ocean Edge Luxury Condo, Constantly Updated, Just steps to Arbor Pool

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Updated 5BR/2BA 2500Sqft Very Private Family Home, WiFi & Air Conditioned!, holiday rental in Brewster

Newly Updated 5BR/2BA 2500Sqft Very Private Family Home, WiFi & Air Conditioned!

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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New Listing at Ocean Edge- Guest Passes Available, holiday rental in Brewster

New Listing at Ocean Edge- Guest Passes Available

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Brewster, MA Beach House with 1/2 Mile of Private Community Beach., holiday rental in Brewster

Brewster, MA Beach House with 1/2 Mile of Private Community Beach.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Ocean Edge 2 BR Townhouse, WiFi A/C Golf Course View Private Backyard, holiday rental in Brewster

Beautiful Ocean Edge 2 BR Townhouse, WiFi A/C Golf Course View Private Backyard

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming And Private Cape Cod Cottage Steps To Saint's Landing Beach On The Bay, holiday rental in Brewster

Charming And Private Cape Cod Cottage Steps To Saint's Landing Beach On The Bay

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Edge- Quiet and Relaxing 2 Bedroom Condo, holiday rental in Brewster

Ocean Edge- Quiet and Relaxing 2 Bedroom Condo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Edge 2 Br Townhouse with central air, private patio, and Resort Access, holiday rental in Brewster

Ocean Edge 2 Br Townhouse with central air, private patio, and Resort Access

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean Edge -3 Bedroom, 3 Full Bath - Largest Size - Popular Location, holiday rental in Brewster

Ocean Edge -3 Bedroom, 3 Full Bath - Largest Size - Popular Location

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 bedrooms. Bay views, 10min walk to beach., holiday rental in Brewster

3 bedrooms. Bay views, 10min walk to beach.

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Cape Cod Rental, Brewster, holiday rental in Brewster

Cape Cod Rental, Brewster

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Dreams Cottage on Paines' Creek, holiday rental in Brewster

Ocean Dreams Cottage on Paines' Creek

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Book it now! Clean cute family-friendly Ocean Edge cond, holiday rental in Brewster

Book it now! Clean cute family-friendly Ocean Edge cond

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Brewster-Ocean Edge Condo, holiday rental in Brewster

Beautiful Brewster-Ocean Edge Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sprawling home on  large, 18-acre estate in Brewster, near the bay beaches, holiday rental in Brewster

Sprawling home on large, 18-acre estate in Brewster, near the bay beaches

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Abutting Nickerson State Park, 1 Mile To Beach - Great for Fall & Winter Stays, holiday rental in Brewster

Abutting Nickerson State Park, 1 Mile To Beach - Great for Fall & Winter Stays

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly listed, the Meadow! Close to Seymour Pond and the Cape Cod Rail Trail., holiday rental in Brewster

Newly listed, the Meadow! Close to Seymour Pond and the Cape Cod Rail Trail.

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tales of Sunset Bay, Paine's Creek Beach-walk to beach, ice cream, coffee & beer, holiday rental in Brewster

Tales of Sunset Bay, Paine's Creek Beach-walk to beach, ice cream, coffee & beer

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Adorable condo w/ patio, full kitchen, shared pool & hot tub-close to the water!, holiday rental in Brewster

Adorable condo w/ patio, full kitchen, shared pool & hot tub-close to the water!

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Apartment on a Private Horse Farm Near Beaches & Woodland Conservation, holiday rental in Brewster

Cozy Apartment on a Private Horse Farm Near Beaches & Woodland Conservation

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Amazing Family Compound - Steps to Crystal Clear Sheep Pond, holiday rental in Brewster

Amazing Family Compound - Steps to Crystal Clear Sheep Pond

5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Walk to the beach and listen to the birds from this comfortable private cottage!, holiday rental in Brewster

Walk to the beach and listen to the birds from this comfortable private cottage!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Beach Access, Great Family Get Away., holiday rental in Brewster

Private Beach Access, Great Family Get Away.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Brewster, MA Beach Cottage with 1/2 Mile of Private Beach for your Enjoyment., holiday rental in Brewster

Brewster, MA Beach Cottage with 1/2 Mile of Private Beach for your Enjoyment.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Picture Perfect Cape Cod Cottage, holiday rental in Brewster

Picture Perfect Cape Cod Cottage

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Walk to Beach from Sea Salt Cottage, holiday rental in Brewster

Walk to Beach from Sea Salt Cottage

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Long Pond Estate w/ Dock & Private Sheep Pond Beach, holiday rental in Brewster

Long Pond Estate w/ Dock & Private Sheep Pond Beach

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Spacious, Comfortable 1700s Home - Close to Cape Cod Bay Beaches, holiday rental in Brewster

Spacious, Comfortable 1700s Home - Close to Cape Cod Bay Beaches

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stroll to Nickerson, Cape Cod Rail Trail, Ocean/Pond Beaches, and Cobie's!, holiday rental in Brewster

Stroll to Nickerson, Cape Cod Rail Trail, Ocean/Pond Beaches, and Cobie's!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern, Magnificent & Private with Heated Pool; 032-B, holiday rental in Brewster

Modern, Magnificent & Private with Heated Pool; 032-B

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Pondfront - Newly Renovated Carriage House on Large Estate, holiday rental in Brewster

Pondfront - Newly Renovated Carriage House on Large Estate

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brewster, MA-Walk to the beach/flats.  4 Bedrooms 3 Bathrooms Sleeps 10, holiday rental in Brewster

Brewster, MA-Walk to the beach/flats. 4 Bedrooms 3 Bathrooms Sleeps 10

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Expansive Cape Less Than 1/10 mile to Ellis Landing Beach, holiday rental in Brewster

Expansive Cape Less Than 1/10 mile to Ellis Landing Beach

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Brewster is Classic Cape Cod - Walk to Beaches, Flats, Restaurants & Bars, holiday rental in Brewster

Brewster is Classic Cape Cod - Walk to Beaches, Flats, Restaurants & Bars

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront on Black Pond and Long Pond, holiday rental in Brewster

Waterfront on Black Pond and Long Pond

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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251 Seaway Brewster 121123, holiday rental in Brewster

251 Seaway Brewster 121123

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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28 Cross St. 116479, holiday rental in Brewster

28 Cross St. 116479

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Elegantly Renovated, Walk 3 Min. to Beach -- 113-B, holiday rental in Brewster

Elegantly Renovated, Walk 3 Min. to Beach -- 113-B

3 bedrooms
1 bathroom
Sleeps 13
Match: Sleeps
More info
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Cape Cod 2 Bdrm Townhome in Brewsters Ocean Edge Resort, holiday rental in Brewster

Cape Cod 2 Bdrm Townhome in Brewsters Ocean Edge Resort

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brewster by the Bay - Spacious house along with a quick walk to the beach, holiday rental in Brewster

Brewster by the Bay - Spacious house along with a quick walk to the beach

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy condo w/ shared pools - near beaches, bike path & Rail Trail!, holiday rental in Brewster

Cozy condo w/ shared pools - near beaches, bike path & Rail Trail!

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sleeps 10 Near Crosby Landing Beach -- 050-B, holiday rental in Brewster

Sleeps 10 Near Crosby Landing Beach -- 050-B

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cape Cod oceanfront rental, holiday rental in Brewster

Cape Cod oceanfront rental

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Two bedroom condo in Ocean Edge with central air, holiday rental in Brewster

Two bedroom condo in Ocean Edge with central air

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 Cottages on sunny property, walk to Brewster bay beach, Cape Cod Rail Trail, holiday rental in Brewster

2 Cottages on sunny property, walk to Brewster bay beach, Cape Cod Rail Trail

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Cozy condo w/ shared pools - near beaches, bike path & Rail Trail!, holiday rental in Brewster

Cozy condo w/ shared pools - near beaches, bike path & Rail Trail!

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Edge Resort Condo 2 Level, 2 Br, Central AC, holiday rental in Brewster

Ocean Edge Resort Condo 2 Level, 2 Br, Central AC

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Big and Beautiful on the Beach in Brewster -- Sleeps 14+: 041-B, holiday rental in Brewster

Big and Beautiful on the Beach in Brewster -- Sleeps 14+: 041-B

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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