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Holiday Homes and Apartments Brewster, MA

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    All 240 Rentals in Brewster
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    Travellers to Brewster are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Studio / 2 Bathrooms / Sleeps 10
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    About this property
    This is a gathering place - 5 sleeping rooms and the home is set up as a duplex with 2 of everything. There are 2 outdoor showers, 2 kitchens, 2 bathrooms, 2 decks, and 2 living areas. Large front and back yards, fully equipped. Beds are: 1 king, 1 queen, 1 double, 5 singles. Located on a quiet... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    Traditional home that has been completely updated with gourmet kitchen (2 ovens-silestone counters-great eat-in space), wood floors with braided rugs, updated bath upstairs, new bedroom with full bathroom in basement, hot outdoor shower, wonderful sunroom surrounded by large windows and sliding... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    Bike the trail, kayak on the pond, or walk and sun on the bay from this great family house. Newly decorated, spacious, bright, and clean home located in beautiful Blueberry Pond neighborhood. Only 1.5 miles to Brewster Bay Beaches, .5 mile to Cape Cod Rail Trail and Nickerson State Park, short... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    Finicky renters please apply. Unwind and relax in this light filled contemporary 2 level home on the pond! Open family room/dining area/kitchen allow for great entertaining. Dine out on the deck or lower patio in this quiet tranquil setting. The first floor has 2 bed/2 baths. The lower finished... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Hot Tub
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    About this property
    Need some time away? Here is a wooded refuge perfect for a large family gathering. This home is located off a country road with nearly an acre of space. Surround yourself with nature while just a short jaunt to the bike (rail) trail, fresh water swimming, the old-time Brewster General Store and... View all property information
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    Brewster, Cape Cod 02631
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    1 Bedroom / 2 Bathrooms / Sleeps 2
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    About this property
    Note: There are two B&B rooms. The pricing is per room. Once the busy summer rental season is over, we limit the rental space in our vacation home to just the two upstairs bedrooms and charge an amazingly low price for each–mainly because we don't offer breakfast (OK, so this is a B and No B!... View all property information
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    Brewster, Cape Cod 02631
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    1 / 9
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    Beautiful Lake Access from immaculate, roomy house in safe cul-de-sac Spacious house with comfortable living space for 10. 5 minute walk to to a beautiful, large, swim and kayak friendly, fresh water lake with private association beach. Two large master suites (one on first floor and one on... View all property information
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    Brewster, Cape Cod 02631
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    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    5 Bedroom, 3 bath ranch with view of Seymour Pond. Central Air, Washer & Dryer, Dishwasher. Short walk to semi private beach. Near bike trail and golf courses. View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    Brewster, Cape Cod 02631
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    1 Bedroom / 2 Bathrooms / Sleeps 9
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    About this property
    Main house with a large bedroom (king bed) and a bathroom, new kitchen and large great room. Patio is perfect for ourdoor cooking, eating and relaxing. very close to main house (not attached) is a cottage or 'Bunkie ' - true bunkhouse with a queen bed-single bed-2 sets of bunk beds-and bathroom.... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    NEW 2015 Listing! An absolutely affordable gem! This lovingly maintained 2 bedroom, 1 bath home is just waiting for you! Just a short walk to Sheep's pond, it has been recently painted and refreshed and is just perfect for that Cape Cod getaway. Ideally located, in addition to access to Sheep's... View all property information
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    Brewster, Cape Cod 02631
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    $3,104
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Contemporary home on over 2 acres-- about 1/2 mile from Cape Cod Bay, but convenient to 6A! Over 3000 square feet of living space make this a wonderful vacation home for the extended family. The terrific chef's kitchen opens out to a bright great room with soaring ceilings and wall of windows that... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    New 2015 Listing!! Dogs Welcome! Bring the whole family, and don't forget Fido! Can't decide between Dennis or Brewster? Now you don't have to! This 3 bedroom, 1 bath ranch is conveniently located on the Brewster / Dennis Town line. Take your pick from nearby Dennis Beaches such as Sea Street... View all property information
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    Brewster, Cape Cod 02631
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    1 / 27
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    Custom, Upscale, Taste & Style - Paines Creek Beach $6,300 PRIME SUMMER WEEKLY RATE (Linens Included) This beautiful custom home is located near Paines Creek Beach, in fact there is only one home between you and the beach. The owner has done a spectacular job of decorating and outfitting this... View all property information
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    Brewster, Cape Cod 02631
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    $1,294
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    Deeded rights to Seymour Pond! This 3 bedroom 2 bath home brings the outdoors in! Spend your days and your nights relaxing on the beautifully designed custom screened in porch with recessed lighting and a ceiling fan. Just a few minutes walk down the street brings you to Seymour Pond, a wonderful... View all property information
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    Brewster, Cape Cod 02631
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    $2,846
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    1 / 19
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Private Outdoor...
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    About this property
    You are going to fall in love with this home! This recently renovated 4 Bedroom, 2 Bath home has something for everyone, including a Pool & Hot Tub! Centrally located in the heart of Brewster with shops and beaches are just a short drive away. The home boasts central AC, a completely updated... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Gym
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    This delightful home is nicely appointed and offers a wonderful open floor plan. The first floor has a bright kitchen with breakfast bar, dining area, living room, bedroom with queen bed, full bathroom and a spacious family room with vaulted ceilings. The second floor has and additional full... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    This is a unique and beautiful house located in the historical district of Brewster, within a short walk to Saint's Landing Beach. This property has a nice and spacious back yard for outdoor enjoyment. All rooms are located on the first floor and A/C units are in both bedrooms and the living room.... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    This well-maintained, three bedroom, two bath home offers something for everyone! Located in the desirable Stonehenge neighborhood in Brewster, this home offers all the creature comforts and is just a short drive to Brewster beaches! This home will book fast, make your reservation today! Wireless... View all property information
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    Brewster, Cape Cod 02631
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    6 Bedrooms / 3 Bathrooms / Sleeps 12
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    Dramatic six-level contemporary home with association access to the freshwater of Blueberry Pond-- just two-tenths of a mile to The Cape Rail Trail. A great room with cathedral ceiling, skylights and hardwood flooring is located at the top level to take advantage of the panoramic view of Cape Cod... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    BEACHFRONT! This beautiful 4 bedroom, 4 bath 'Upside Down' layout home features breathtaking panoramic views of Paine's Creek and Cape Cod Bay from every level. It's spacious layout offers sleeping for up to 10, so bring the whole family! The first level of the home offers a roomy living area with... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    100 PILOTS WAY BREWSTER 1920’s classic bungalow, completely modernized and now air conditioned! Gem of the neighborhood in family-friendly Pineland Park. Less than 1/10-mile barefoot walk on a sandy road to the beach! Three bedrooms, 1 1/2 baths, updated eat-in kitchen with granite counter... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    251 SEAWAY BREWSTER Air conditioned beach house, four large bedrooms, two full baths. Sleeps 8 with one queen, one double and 4 twins. 100 yards to private Pineland Park Association beach. Custom upside-down design provides great views of Cape Cod Bay from second floor living-dining area and... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Central AC for 2015! This lovely 2 bedroom, 1 bath home is located on the very desirable Grandfather's Lane in Brewster. Just steps from a private association beach, it offers the vacationer a budget friendly Cape Cod Getaway! Relax on the screened in porch while listening to the ocean waves, as... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    Swimming, boating, and fishing in a beautiful fresh water lake is just a half block from this open, spacious, crisp 3 bedroom 3 bath home with a great deck for family BBQ's and a finished basement for additional entertainment space. This home has membership to a private association beach on Seymour... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    Renovated beauty on the beach in Brewster $5,800 PRIME SUMMER WEEKLY RATE The property is as close to the water as you can get! 4 steps from the main level deck brings you to the private stairs down to the private beach only shared by 3 other homes. Cape Cod Bay provides warm calm water and of... View all property information
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    Brewster, Cape Cod 02631
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    $2,458
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    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    3 Minutes to Beach, Big, Roomy, 4 BR, 4 Baths$4,400 PRIME SUMMER WEEKLY RATE OFF-SEASON WEEKS AVAILABLE FROM $2,000! Off-season minimum 3 nights. This house really has something for everyone. We think it is one of the more comfortable and fun houses for a group since there are so many places to be... View all property information
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    Brewster, Cape Cod 02631
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    $2,846
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    Custom Built New Home, 3 Minutes To Beach$5,200 PRIME SUMMER WEEKLY RATE Please Note: This property rents Sunday to Sunday during July and August. See tempting off-season rate reductions for June and September It's a custom built home in the Ellis Landing Beach section of East Brewster with a... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Water Views
    • Wi-Fi
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    • x
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    Water views, 150 feet to private beach$4,500 PRIME SUMMER RATE It's a two-story vacation home with wonderful views of Cape Cod Bay from practically every room. The family room is on the second floor to take maximum advantage of the view. There are 4 bedrooms and 2 full baths. The master bedroom is... View all property information
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    Brewster, Cape Cod 02631
    From
    $4,139
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Dishwasher
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    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    Walk to Sheep's Pond, Brewster, sleeps 10$3,400 PRIME SUMMER WEEKLY RATE Nestled on a private lot in a private Sheep's Pond neighborhood, this well equipped vacation home offers a unique Brewster experience. Just a 3-5 minute walk down a scenic wooded trail brings you to the north shore of pristine... View all property information
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    Brewster, Cape Cod 02631
    From
    $4,527
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    VACATION IN LATE AUGUST, SAVE $800 OFF PRIME SUMMER RATE! AUGUST 24-31 NOW AVAILABLE AT $4,900! Please note: This property rents Sunday to Sunday. It has a beautiful location, right on a private sandy neighborhood beach. The yard and screened porch facing the Bay are extremely private and... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $5,821
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    Loads of Living Space at New home by beach!$6,800 PRIME SUMMER WEEKLY RATE Please note: This property rents Sunday to Sunday. The beautiful house was built in 2007 and includes all the modern amenities: central AC, wireless Internet, granite countertops, a brick patio as well as a mahogany deck... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $539
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    Directly on the Bay in Brewster with AC $4,000 PEAK SUMMER WEEKLY RATE It's rare to find a Brewster family cottage with this much seclusion, directly on a private neighborhood beach! Perched atop the dunes and virtually invisible from surrounding homes, you get the feeling that you have Cape Cod... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $453
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    1 / 34
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
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    • Dishwasher
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    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Spacious, Updated Value, 2 Minutes to Beach $3,300 PRIME SUMMER WEEKLY RATE Enjoy off-season rates from $1300/week Off-season minimum: three nights Here's one of the best private home vacation values you'll find in Brewster. Just a two minute walk from one of the town's best private association... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $830
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    1 / 27
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Dishwasher
    • Grill
    • Satellite TV
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    Spotless Home, 1 Minute Walk to Beach $4,500 PRIME SUMMER WEEKLY RATE Note: This property rents Sunday to Sunday This home is on a very private, tiny unpaved cart way which ends right at the driveway to this house. A 45-second walk takes you up a short, shaded path, directly in front of the house,... View all property information
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    Brewster, Cape Cod 02631
    From
    $5,433
    / Week
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    Sweet Cottage on Private Bayside Beach PRIME SUMMER WEEKLY RATE: $3,700 You can't beat the location. It's directly on one of the best private sandy beaches on the Bay. The tide goes way out at low tide, making it a terrific playground for kids of all ages. The large covered porch adds bonus living... View all property information
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    Brewster, Cape Cod 02631
    From
    $9,572
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    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    Togetherness & privacy in big Bayside home $6500 PRIME SUMMER WEEKLY RATE It is a house meant for family and friends to gather. There is space to be together as well as space to be apart. There is a living room as well as a family room off the kitchen. Both have been redone for summer 2014 by the... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $479
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Enquiry
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    • Dishwasher
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    • Water Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    Nice & Roomy, 4 Minute Walk to Sandy Beach$3,800 PRIME SUMMER WEEKLY RATE Please note: This property rents Sunday to Sunday. There is living space on three levels in this house. There's a good sized living room on the main level, which flows into the open dining area and out to the screened porch.... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $5,756
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    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    Cheery Cape Beach Cottage Directly on Bay $3,900 PRIME SUMMER WEEKLY RATE A classic, yet updated Cape Cod cottage, directly on a perfect sandy, private association beach. There is 450 feet of beach front, with private access from only 13 cottages including this one. Consequently, the beach is never... View all property information
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    Brewster, Cape Cod 02631
    From
    $4,463
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    Elevated lake views with upscale privacy $3,200 PRIME SUMMER WEEKLY RATE Book July 4th Week, Stay an Extra Night at 50% Off! Please call for details: 508 896-3241 The home is directly on Blueberry Pond, a 25-acre fresh water lake. The lake is great for canoeing, fishing and relaxing. A canoe is... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $11,771
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    5 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    Upscale cottage, right on the beach! $8,000 PRIME SUMMER WEEKLY RATE If you're looking for the ultimate beachfront experience, consider Summerwinds, this one-of-a-kind upscale bungalow on the Bay in Brewster. From the renowned artists' work adorning the walls to the luxurious bed linens and terry... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $5,433
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    Striking Bay & Crosby Landing Beach Vista $3,900 PRIME SUMMER WEEKLY RATE Book July 4th Week, Stay an Extra Night at 50% Off! Please ask for details: 508 896-3241 The first thing that strikes you when you drive up to this house is how secluded it is from neighboring properties, tucked at the end of... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $3,234
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    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    Sleeps 12, One Minute Walk to Perfect Private Beach $4,900 PRIME SUMMER WEEKLY RATE Off-season weekly rates from $2,500 Off-season weekends and partial weeks also considered NOTE: This property rents Sunday to Sunday Tucked into a secluded, treed lot in a small, quiet Bayside neighborhood, this... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $5,821
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    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    New & Upscale, Near Lakes, Bike Trail, Sleeps 12$4,500 PRIME SUMMER WEEKLY RATE If you've got a group of up to 12 and want a new home with upscale amenities throughout, this could be your best vacation choice. It's part of a new neighborhood in the scenic lakes section of Brewster at the Harwich... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $3,234
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    5 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    Breathtaking Views Directly On Sandy Beach $5,200 PRIME SUMMER WEEKLY RATE Please note: This property rents Sunday to Sunday. This family beach house is directly on a private, sandy beach in Brewster - one of the best beaches on the Bay. The house is ideally situated to take best advantage of the... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $7,890
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    Secluded home on the beach on Cape Cod Bay! $5,400 PRIME SUMMER WEEKLY RATE What a great location! Dune Road is an unpaved quiet road that runs parallel to the beach. The house sits on a private treed lot with fantastic views of the water. There is a small private path from the back yard to the... View all property information
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    Location Information
    Brewster, Cape Cod 02631
    From
    $5,045
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    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
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    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    Beachfront cottage, panoramic Bay views$3400 PRIME SUMMER WEEKLY RATE When most vacationers picture a Cape Cod beach front cottage, this is the image that comes to mind. From its perfect perch above the Bay you have panoramic 180-degree water views. The steps down to the beach are just off the... View all property information
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    Location Information
    Brewster, Cape Cod 02631