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Vacation Rentals and Cottages in Brewster, MA

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    1 / 11
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 13
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Street Level, Updated Kitchen, 2 ACs, WIFI & 6 Pool Passes (fees apply) - This nicely decorated property has updates that include newer kitchen cabinets and fixtures. The sunny master bedroom has a queen bed, AC, TV, private bath, and sliders to the patio. The 2nd bedroom has 2 twin beds and a... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Great opportunity to rent this 4 bedroom house starting at $1000 per week. This charming home is located less than a mile from Breakwater Beach and a short distance from the Brewster General Store. The first floor offers a kitchen with a separate dining room, ample living room with a flat screen... View all property information
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    Brewster, Cape Cod
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Walk to Paines Creek Beach, Dog Friendly, Renovated Kitchen, AC, WIFI - This darling 1 bedroom, 1 bath, duplex style cottage is just a 5 minute walk to beautiful Paines Creek Beach where you can watch breathtaking sunsets and explore tidal pools at low-tide. This Brewster flats beach is a... View all property information
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    Brewster, Cape Cod
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Short walk to Upper Mill Pond, 2.3 miles to beautiful Paines Creek Beach on the Bayside, WIFI - Located in a private setting this 3 bedroom 2 bath single level home is just a half mile from a shared private association beach at Upper Mill Pond. The master bedroom has a queen size bed with... View all property information
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    Brewster, Cape Cod
    1 / 14
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Upper Level, End Unit, Updated Kitchen, 1 AC, WIFI This tastefully decorated, Eaton Village apartment features sunny rooms and private wooded views. The master bedroom has a queen bed, TV with VCR, and private bath. The 2nd bedroom has 2 twins and TV with DVD. Both bedrooms have ceiling fans... View all property information
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    Brewster, Cape Cod
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    READY TO RENT FOR 2017 Private Dock on Lower Mill Pond, Waterviews & WIFI Built in 2004, this recently painted home faces southwest on Lower Mill Pond for magnificent sunsets in a beautiful, secluded setting. Take a morning dip in the pond from your own private dock just 50 feet from the... View all property information
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    Brewster, Cape Cod
    1 / 12
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    A-Style, Renovated, Straight Staircase, 2 ACs, WIFI & 6 Pool passes (Fees Apply) - This spacious, renovated Howland Village townhouse is beautifully decorated and features a straight staircase and Pergo flooring throughout the main floor. You'll find the master bedroom upstairs with a queen... View all property information
    Location Information
    Brewster, Cape Cod
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    1 / 8
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Upper Level, 1 AC, WIFI & 6 Pool Passes (Fees Apply) - This is a lovely Eaton Village apartment with cathedral ceilings and peeks of the golf course from the deck. The master bedroom has a queen bed, TV and private bath. The 2nd bedroom has 2 Twin beds and a TV. The kitchen has all the... View all property information
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    Brewster, Cape Cod
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    B-Style, King Bed, Straight Staircase, 1 A/C WIFI & 6 Pool Passes (Fees Apply) - This tastefully decorated townhouse located at the entrance of Billington Village is a short walk to Arbor pool and features newer carpeting and paint. The master bedroom is located on the first floor and offers a... View all property information
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    Brewster, Cape Cod
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A-Style, Pond & Golf Course Views, 2 ACs & WIFI - This spacious Billington Village townhouse has lovely pond and golf course views that can be seen from the living room and patio. The first level offers a full bathroom, a fully equipped kitchen and dining area, a living room with AC and large,... View all property information
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    Brewster, Cape Cod
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    B-Style, Renovated, King Bed, Straight Staircase, Enclosed Loft, 2 ACs, WIFI & 6 Pool Passes (Fees Apply) - Recently Reduced: 7/2 - 7/9 by $200! This beautiful, Howland Village townhouse features many updates that include a straight staircase, wood floors, newer carpet, updated kitchen and... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 12
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    B-style, Updated, Enclosed Loft, 3 Ductless AC's, WIFI, & 6 Pool Passes (Fees apply) - This is a nicely updated Billington Village 2 bedroom, 2 bath townhouse that features solid flooring throughout both levels, an enclosed loft bedroom, and views of the 9th hole. You'll find the master... View all property information
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    Brewster, Cape Cod
    1 / 10
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Porch
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    • x
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    • x
    About this property
    Great 3 bedroom home located on a cul -de -sac with a very short walk to Linnell Landing Beach and beautiful sunsets. Large screened porch with cable TV and a covered patio with built in barbecue grill. A gas grill is also available. Nearby is Nickerson State Park, bike paths, live theater and... View all property information
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    Brewster, Cape Cod
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    Upper Level, Queen Bed & 2 Twin Beds, Pull out Sofa Bed, 1 AC, WIFI & 6 Pool Passes (Fees Apply) This very nicely decorated and charming Eaton Village apartment is located on the 2nd floor with cathedral ceilings. The unit is a short walk (<5 minute) to Fletcher Indoor/Outdoor Pool, Tennis... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    Lower Level, Murphy Bed, 3DTV, 1 AC, WIFI & 4 Pool Passes (Fees Apply) - This lower level (downstairs from the street entrance), Fletcher Village apartment is located across from the Fletcher pools and tennis courts and features a 3D TV and a newer, memory foam mattress in the bedroom. The... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Patio
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    • x
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    • x
    About this property
    B-Style, Close to Fletcher Pools, 1 AC, WIFI & 5 Pool Passes (Fees Apply) - This sunny townhouse is located at the entrance to Howland Village. The first floor master bedroom has a queen bed and TV. Up the spiral staircase, you will find the 2nd bedroom (open loft) which offers a full bed plus... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Bayside, Central AC, WIFI & Beach #2, Bayside Pool #2 & Bayside Tennis #2 - Located on Mariner Court, this lovely townhouse is a short walk to the private association beach on Cape Cod Bay and is across the way from the association pool and tennis courts. This home offers 3 good size bedrooms,... View all property information
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    Brewster, Cape Cod
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    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Hot Tub
    • Shared Indoor Pool
    • DVD Player
    • Air Conditioning
    • Sauna
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Make our sunny and bright home your vacation retreat. This is a family friendly townhouse. You will appreciate the only 2 minutes walk to the Fletcher indoor/outdoor pool complex ( pool passes included*). Park your car right in front of the house and come in. Enjoy the warmth of this two story... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Upper Level, Updated Kitchen, 2 ACs, & WIFI - This is a very nice Eaton Village apartment that features newer furniture, an updated kitchen, and a 46 inch flat screen TV. The master bedroom has a queen bed, TV, AC, and private bath. The 2nd bedroom has 2 twins and TV with DVD. The fully... View all property information
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    Brewster, Cape Cod
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • x
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    • x
    About this property
    At the end of a cul de sak this home is nestled between Canoe Pond and Upper Mill Pond with a deeded beach just steps away! This Comfortable 2 level home has all the comforts that you require. The Open Floor plan boasts a fire placed Living room (Queen size fold out sofa) with an adjacent dining... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    A-Style, Straight Staircase, 2 ACs, WIFI - This is a lovely Billington Village townhouse. The first floor master bedroom has a queen bed and a TV. Up the straight staircase is the 2nd bedroom, which features 2 twin beds, AC, TV, and a private bath. The adjoining open loft has a trundle bed (2... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Upper Level, King Bed & Queen Bed, 1 AC, WIFI & 6 Pool Passes (Fees Apply) - This nicely decorated, 2nd floor Eaton Village apartment has recently had new appliances and carpeting installed. The master bedroom has a queen bed, a ceiling fan, a TV with DVD, and a private bath. The 2nd bedroom... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    B-Style, King Bed, Renovated, 2 ACs, WIFI & 6 Pool Passes (Fees Apply) - This lovely, Howland Village townhouse is privately located and has many updates; including Pergo floors, renovated bathrooms and a new (2013) ductless AC unit to cool the property. You will find the master bedroom on the... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 13
    5 of 5 stars (6) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Dog Friendly, Sheep Pond with Private Association Beach, Renovated, 2 ACs & WIFI - This stunning, ONE OF A KIND PROPERTY with access to Sheep Pond was completely renovated in 2010 and the professionally decorated interior with bamboo flooring was featured in a Cape Cod design magazine (Cape Cod... View all property information
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    Brewster, Cape Cod
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This charming, immaculately kept Cape is about 2 miles to Captain’s Golf Course, just over a mile to swimming, boating and fishing on Pleasant Bay, and a short drive to Harwich or Orleans shopping centers, theaters, etc. The kids will enjoy the yard by day and the lower level play area/den by... View all property information
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    Brewster, Cape Cod
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • ?
    About this property
    Walk to Brewster's beautiful Crosby Landing Beach, one of Cape Cod's most desirable bay beaches from this spacious, stylish, and privately situated home. Attractively furnished, impeccably maintained and fully equipped, this 3-BR, 2-Bath ranch sleeps six-to-nine. It is configured to happily... View all property information
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    Brewster, Cape Cod
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    FRI to FRI rental gives you 6 more hours to enjoy the Cape instead of sitting in the Saturday traffic! New to rental market in 2014. Modern home on 3.2 acres of beautiful wooded property that will get you in vacation mood the moment you drive in on a long winding driveway to get to the waterfront... View all property information
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    Brewster, Cape Cod
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Upper Level, Murphy Bed, 2 ACs & 4 Pool Passes (Fees Apply) - This bright, updated, Fletcher Village apartment overlooks the golf course from the deck. The air-conditioned bedroom has a queen bed and ceiling fan. The fully equipped kitchen has all the amenities of home and there is a dining area... View all property information
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    Brewster, Cape Cod
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Middlecott Village Patio Home with loft - sleeps 6. Central Air and WiFi! This property currently includes pool privileges which are available at an additional fee.* Spend hours on the over-sized patio and enjoy the excitement of golf right in front of you, or the tranquility of the pond to your... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 11
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Patio Style with Full 2nd Floor, King bed, WIFI, Central AC & 8 Pool Passes (Fees Apply) - This is a one-of-a-kind, stunningly renovated, end-unit patio home located on the 15th tee in Susanna Village. Enjoy a quality, Cape Cod home that is cozy and unique among the patio homes in Ocean Edge.... View all property information
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    Brewster, Cape Cod
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ACCESS TWO DIFFERENT FRESH WATER PONDS FROM THIS GREAT 3 BEDROOM RENTAL HOME IN BREWSTER! This house sits across the street from Walkers Pond and boat ramp for easy access with a kayak or small boat. A short walk down the path behind the house will bring you to Pine Pond and the association beach... View all property information
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    Brewster, Cape Cod
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
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    Water Views and Dock on Sheep Pond, WIFI Enjoy the pond view with only a few steps to a private dock where you will enjoy jumping off into the warm Cape Cod pond waters. And, just a few minutes' walk away is the nationally famous Cape Cod Rail Trail Bike Path. This lovely cottage with WIFI is... View all property information
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    Brewster, Cape Cod
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Rustic yet charming, this lakefront cottage provides privacy and spectacular waterviews from every room. Pets are welcome! Multiple sliding doors open to a private wrap around deck with lounge chairs, dining table, gas outdoor grill and an outdoor shower; all for your entertaining pleasure.... View all property information
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    Brewster, Cape Cod
    1 / 13
    2.5 of 5 stars (2) Poor
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Street Level, 2 King Beds, Renovated Kitchen, 4 ACs, WIFI & 8 Pool Passes (Fees Apply) This very spacious, Endicott Village apartment is a short walk to the Arbor Pool and Linx Tavern restaurant. The unit features upgrades to 2 bathrooms and the kitchen. The master bedroom has a king size bed,... View all property information
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    Brewster, Cape Cod
    1 / 21
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    Just 1500 ft. to Private Beach!! This gorgeous 4 bedroom, 2 bath Brewster vacation rental home is located just 2/10th of a mile to a fantastic neighborhood beach on Cape Cod Bay. This lovely home is done in and out. The amenities include washer / dryer, A/C, internet, cable TV, DVD, deck, deck... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 39
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Hello & Welcome to my Two Bedroom - Two Bath Townhouse which is an End Corner Duplex and is located in Brewster on the Premier Ocean Edge Resort & Golf Club Property~Sponsored Guest Passes are Available for Golf~Tennis~Pool and NEW! Kayaking/Paddle Boarding on Blueberry Pond at the Guest Policy... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 8
    4 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    C-Style, Straight Staircase, 2 ACs, WIFI & 6 Pool Passes (fees apply) - This cheerfully decorated Billington Village townhouse is ideal for the family get-away and features Pergo flooring in the dining and living room areas. Both bedrooms are located upstairs; accessed by a straight staircase.... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Porch
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charismatic Cape Cod house, built in the 20s by the groundskeeper for a nearby estate, shows post and beam construction, rambling New England Extended Architecture accented with all new, sustainable renovation right down to the appliances. Gather your family and friends in this beautiful Brewster... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Upper Level, 1 AC, & WIFI - This is a lovely end-unit, 2 bedroom, 2 full bath apartment in Eaton Village that overlooks the 5th green. The master bedroom has a queen bed, TV, and a private bath. The 2nd bedroom has 2 twin beds. The kitchen is fully equipped and there is comfortable seating in... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 14
    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Hot Tub
    • Satellite TV
    • Sauna
    • Air Conditioning
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    - 2 bedroom C-style townhouse in Ocean Edge Resort. 1 1/2 baths, AC, HDTV, Wi-Fi, free phone, washer & dryer and dishwasher. - Private patio with BBQ grill. - Resort swimming pools, whirlpools, fitness center and amenities access. (passes need to be acquired directly at the resort (2015... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 9
    1 of 5 stars (1) Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Internet Access
    • Parking
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    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    READY TO RENT FOR 2017 C-Style, Straight Staircase, Updated Flooring, 2 new A/Cs, WIFI & 6 Pool Passes (Fees Apply) - This bright & cheery Howland Village townhouse features laminate flooring throughout the main floor, newer carpeting upstairs, and new AC units. Up the straight staircase,... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 14
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • DVD Player
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A-Style, King Bed, Renovated, 2 ACs, WIFI & 6 Pool Passes (Fees Apply) - This beautiful townhouse in Billington Village features a newly renovated (2014) kitchen, Pergo flooring in the living/dining area, renovated bathrooms, and wooded views. The master bedroom is up the spiral staircase and... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 13
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Satellite TV
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Short walk to a private path to Cape Cod Bay. Extensive renovations make this home the perfect place for your vacation. This classic summer home sits at the end of a sandy lane. Updated from stem to stern this great home has 5 bedroom, 2 full baths, Internet, outdoor shower, large back deck,... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 4
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Situated down a lane surrounded by woods, lawns & flower gardens our home is an oasis from the busy Cape Cod summer. The house sits on over 2 1/2 acres of privacy. We are located within 1 mile of both salt and fresh water swimming, boating and fishing. Close by are a number of world class golf... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 6
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Street Level, Renovated, 1 AC, WIFI This is a nicely renovated 2 bedroom, 2 bath, Eaton Village apartment. The master bedroom offers a queen bed, AC, and a TV. The 2nd bedroom has 2 twin beds. The updated kitchen is fully equipped with modern appliances, and there is a dining area with seating... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Outdoor adventures are just minutes away from our nature-surrounded home in Cape Cod. Take the family on a woodland hike, cycle along tree-lined trails, go kayaking on glittering blue lakes, or build sandcastles on the golden sands of Breakwater Beach. Or relax at home! Our private fenced... View all property information
    Location Information
    Brewster, Cape Cod
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Grill
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    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    419 Paines Creek, Brewster -(ID# 29143) Summer-time condo duplex only 2/10 of a mile to Paines Creek Beach. One bedroom, one bath with living room/ kitchen area, sleeping porch and patio off of the back provide additional living area. Modern amenities, but the charm is there. No Pets Accepted.... View all property information
    Location Information
    Brewster, Cape Cod