Vacation Rentals in Brewster, Massachusetts

50 Properties Available

$8M Beach House on the Dunes of Cape Cod Bay (New construction 2021) Private vacation home
$8M Beach House on the Dunes of Cape Cod Bay (New construction 2021)
$4749 / night
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Spectacular Coastal Living w salt water pool, close to beach & air conditioned Private vacation home
Spectacular Coastal Living w salt water pool, close to beach & air conditioned
$2574 / night
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Long Pond Luxury Estate. Private Dock, Private Beach Access, Pickleball Private vacation home
Long Pond Luxury Estate. Private Dock, Private Beach Access, Pickleball
$1419 / night
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Beautiful, private, spacious, 5BR - huge 20 x 40 pool, central AC Private vacation home
Beautiful, private, spacious, 5BR - huge 20 x 40 pool, central AC
$862 / night
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Brewster Farmhouse Retreat on Seymour Pond Private vacation home
Brewster Farmhouse Retreat on Seymour Pond
$764 / night
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This lovely Brewster home is 0.8 mile to 2 Cape Cod Bay beaches and access to the popular bike trail Private vacation home
This lovely Brewster home is 0.8 mile to 2 Cape Cod Bay beaches and access to the popular bike trail
$746 / night
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Private Lake Beach on Bike Path, Air Conditioning, Outdoor Patio w/Fire Place. Private vacation home
Private Lake Beach on Bike Path, Air Conditioning, Outdoor Patio w/Fire Place.
$741 / night
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Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds! Private vacation home
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
$734 / night
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Seaside Breeze Private vacation home
Seaside Breeze
$698 / night
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2 Mi to Beach! Cape Cod Family Retreat w/ Deck Private vacation home
2 Mi to Beach! Cape Cod Family Retreat w/ Deck
$673 / night
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Large Ocean Edge House - Sleeps 8. Pools, Pickleball & Golf Private vacation home
Large Ocean Edge House - Sleeps 8. Pools, Pickleball & Golf
$642 / night
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Four bedroom home within walking distance to Bayside Brewster beaches! Private vacation home
Four bedroom home within walking distance to Bayside Brewster beaches!
$640 / night
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Ocean Edge Luxury Condo, Constantly Updated, Just steps to Arbor Pool Condo
Ocean Edge Luxury Condo, Constantly Updated, Just steps to Arbor Pool
$631 / night
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Steps to Bayside Beach, Central AC, Large Backyard! Private vacation home
Steps to Bayside Beach, Central AC, Large Backyard!
$623 / night
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Pond Access, Fire Pit & Bikes, house with AC in charming Brewster Private vacation home
Pond Access, Fire Pit & Bikes, house with AC in charming Brewster
$615 / night
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Brewster Retreat Near Bay Beaches & Dining Private vacation home
Brewster Retreat Near Bay Beaches & Dining
$612 / night
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Shady Pines Private vacation home
Shady Pines
$603 / night
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Luxurious Susanna Patio Home in Ocean Edge, that has all the bells and Whistles! Condo
Luxurious Susanna Patio Home in Ocean Edge, that has all the bells and Whistles!
$581 / night
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Well equipped In The Heart Of Brewster-minutes to the beach Newly renovated Private vacation home
Well equipped In The Heart Of Brewster-minutes to the beach Newly renovated
$572 / night
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Lakefront - Long Pond, Brewster: On the water, kayak, swim, fish, relax! Private vacation home
Lakefront - Long Pond, Brewster: On the water, kayak, swim, fish, relax!
$571 / night
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Updated in 2024! 2BR\/2Ba at Ocean Edge Resort Condo
Updated in 2024! 2BR\/2Ba at Ocean Edge Resort
$555 / night
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Spring break special! Private vacation home
Spring break special!
$550 / night
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Little slice of heaven, only about 300 yards to the crystal-clear sparkling Sheep Pond in Brewster. Private vacation home
Little slice of heaven, only about 300 yards to the crystal-clear sparkling Sheep Pond in Brewster.
$534 / night
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Cozy apartment on a private horse farm near the beaches and forest conservation Apartment
Cozy apartment on a private horse farm near the beaches and forest conservation
$532 / night
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Sears Point end unit Condo
Sears Point end unit
$524 / night
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Cape Cod Bay & Quivett Creek Views-Great Sunsets! Private vacation home
Cape Cod Bay & Quivett Creek Views-Great Sunsets!
$524 / night
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BREWSTER, Private Beach Summer Rental, 4 bdrm, 2ba, (SLEEPS 8) Private vacation home
BREWSTER, Private Beach Summer Rental, 4 bdrm, 2ba, (SLEEPS 8)
$522 / night
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Less than half a mile to the Private Association Beach with Fire Pit and Outdoor Shower. Private vacation home
Less than half a mile to the Private Association Beach with Fire Pit and Outdoor Shower.
$508 / night
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A SHORT STROLL TO LINNELL LANDING BEACH - DON’T MISS OUT ON SUMMER 2024! Private vacation home
A SHORT STROLL TO LINNELL LANDING BEACH - DON’T MISS OUT ON SUMMER 2024!
$500 / night
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Ocean Edge Townhome - Renovated & Spotless w/AC! Condo
Ocean Edge Townhome - Renovated & Spotless w/AC!
$483 / night
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The Mansion at Ocean Edge Hotel
The Mansion at Ocean Edge
$475 / night
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\"BLUEBERRY ACRES\" - 1\/2 mile to Breakwater Bayside Beach in Brewster, a wonderful Cape Cod Bay beach Private vacation home
\"BLUEBERRY ACRES\" - 1\/2 mile to Breakwater Bayside Beach in Brewster, a wonderful Cape Cod Bay beach
$470 / night
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Private Oasis Near Rail Trail, Beaches, Dining (2425) Private vacation home
Private Oasis Near Rail Trail, Beaches, Dining (2425)
$460 / night
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Sunlit townhome at Ocean Edge Resort in Brewster- central A\/C, pool privilege's Condo
Sunlit townhome at Ocean Edge Resort in Brewster- central A\/C, pool privilege's
$459 / night
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Wow! Private Pool, Game Room, and Fire Pit! Private vacation home
Wow! Private Pool, Game Room, and Fire Pit!
$452 / night
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Beautiful large Ocean Edge Townhome in Brewster on Cape Cod! Condo
Beautiful large Ocean Edge Townhome in Brewster on Cape Cod!
$448 / night
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SPACIOUS & POND FRONT! Private vacation home
SPACIOUS & POND FRONT!
$442 / night
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Beautiful Home Close to Ponds and Beach! Private vacation home
Beautiful Home Close to Ponds and Beach!
$440 / night
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Spacious 4 bedroom\/3bath, on the Brewster\/Orleans line Private vacation home
Spacious 4 bedroom\/3bath, on the Brewster\/Orleans line
$435 / night
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House on Koi Pond - Brewster Private vacation home
House on Koi Pond - Brewster
$433 / night
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Come and enjoy this beautiful Brewster residence for your Cape Cod summer vacation with Central A\/C! Private vacation home
Come and enjoy this beautiful Brewster residence for your Cape Cod summer vacation with Central A\/C!
$431 / night
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Classy, Comfy, and Convenient with AC & Pool Access Condo
Classy, Comfy, and Convenient with AC & Pool Access
$425 / night
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Walk to Private Bayside Beach! Private vacation home
Walk to Private Bayside Beach!
$406 / night
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Beachy Unit Overlooking Golf Course Condo
Beachy Unit Overlooking Golf Course
$405 / night
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Ocean Edge Mansion side Condo
Ocean Edge Mansion side
$404 / night
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WONDERFUL FAMILY HOME: CENTRAL AIR, BEACH NEARBY,\nSUNDAY TO SUNDAY RENTAL Private vacation home
WONDERFUL FAMILY HOME: CENTRAL AIR, BEACH NEARBY,\nSUNDAY TO SUNDAY RENTAL
$404 / night
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On the North Side of 6A in Brewster, just a stone's throw away from the picturesque Cape Cod Bay. Private vacation home
On the North Side of 6A in Brewster, just a stone's throw away from the picturesque Cape Cod Bay.
$403 / night
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HISTORIC LUXURY! Patio-firepit-2KingSuites Private vacation home
HISTORIC LUXURY! Patio-firepit-2KingSuites
$401 / night
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Saints Landing and Mants Landing Beach. Come and enjoy the amazing Brewster beaches on Cape Cod Bay. Private vacation home
Saints Landing and Mants Landing Beach. Come and enjoy the amazing Brewster beaches on Cape Cod Bay.
$392 / night
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Charming Brewster Family Getaway!! Central air & Pet Friendly! Private vacation home
Charming Brewster Family Getaway!! Central air & Pet Friendly!
$389 / night
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