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Holiday Rentals and Homes in Brewster, MA

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    Travellers to Brewster are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 21
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 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 private bath.... View all property information
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    Brewster, Cape Cod 02631
    1 / 13
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    3 bedrooms, 2 master suites, central air, large private yard, near Paines Creek Beach on Cape Cod Bay. View all property information
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    Brewster, Cape Cod 02631
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    READY TO RENT FOR 2017 A-Style, Pond & Golf Course Views, 2 ACs 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... View all property information
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    Brewster, Cape Cod 02631
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A-Style, Straight Staircase, 2 ACs 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 twins... View all property information
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    Brewster, Cape Cod 02631
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    This quintessential beach cottage has views of Cape Cod Bay from the front yard. Gorgeous vacation home just .1 mile to a private association beach on Cape Cod Bay! You will love the screened in porch, a wonderful outside shower, and a simply relaxing and charming atmosphere. Home has 4 large... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Bay Views and Short Walk to Grandfather's Beach, Renovated Kitchen, Central AC Take in the stunning sunsets from the spacious deck of this 4 bedroom, 3 bath home that overlooks Cape Cod Bay and is located steps away from Grandfather's Beach in Brewster (a private association beach). This spacious... View all property information
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    Brewster, Cape Cod 02631
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Patio Style with Loft, Renovated, Fully Air Conditioned, 6 Pool Passes (Fees Apply) This beautiful patio home in Allerton Village has been renovated and features solid flooring throughout the main floor, and a new ductless AC system (2016). The first floor, master bedroom has a queen bed, TV with... View all property information
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    Brewster, Cape Cod 02631
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    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    READY TO RENT FOR 2017 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... View all property information
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    Brewster, Cape Cod 02631
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    2.5 of 5 bubbles (2) Poor
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Street Level, 2 King Beds, Renovated Kitchen, 4 ACs & 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, TV,... View all property information
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    Brewster, Cape Cod 02631
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    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    READY TO RENT FOR 2017 Dog Friendly, Sheep Pond with Private Association Beach, Renovated, 2 ACs 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... View all property information
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    Brewster, Cape Cod 02631
    1 / 8
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    C-Style, Straight Staircase, 2 ACs, 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. The... View all property information
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    Brewster, Cape Cod 02631
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Street Level, 1 AC, Updated, 4 Pool Passes (Fees Apply) This lovely Eaton Village apartment is located in a quiet area and features peeks of the golf course, solid flooring throughout the entire unit, and an updated kitchen. The master bedroom has a queen bed, TV and private bath. The 2nd... View all property information
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    Brewster, Cape Cod
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Totally renovated home capturing the charm of yesteryear with the convenience of today. This home features kitchen with stainless steel appliances, open floor plan, master bath with whirlpool tub and separate shower and first floor laundry room. The home is tastefully furnished and well... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Private Beach at just 50 ft!! Enjoy this gorgeous Brewster vacation rental that is located in an exclusive area of lovely Brewster Cape Cod. At this 2 bedroom, 1 bath home you will be just 50 ft. from one of the most exclusive and beautiful Cape Cod bay beaches. There are granite counter tops in... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    This Brewster rental home is located on a private dirt cul-de-sac just apprx. 1/4 of a mile to Ellis Landing beach on Cape Cod bay. From this home you can walk to the beach and up to 6A for restaurants and convenient store. There are 3 bedrooms and 1 full bathroom. The first bedroom has a full, the... View all property information
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    Brewster, Cape Cod 02631
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    28 Cross St., Brewster -Property ID: 116479 This lovely home is just 1/10 mile to a private association beach on Cape Cod Bay. Spacious living areas on both 1st and 2nd floors with 5 bedrooms, 2 full baths, plus an enclosed outdoor shower. Close to Brewster restaurants and ice cream after soaking... View all property information
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    Brewster, Cape Cod 02631
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    READY TO RENT FOR 2017 Street Level, Updated Kitchen, 2 ACs, 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... View all property information
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    Brewster, Cape Cod 02631
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    1 / 14
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    251 Seaway Brewster (ID# 121123) ~ Pineland Private Beach Association 2017 Season! Air conditioned beach house, four large bedrooms, and two full baths. Sleeps 8 with two queens, and 4 twins. 100 yards to private Pineland Park Association beach. Custom upside-down design provides great views of... View all property information
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    Brewster, Cape Cod 02631
    1 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Spacious 4 Bedroom Vacation Rental Home in Brewster on quiet residential lane -sleeps 10 -perfect for your family. Peak Summer Weekly Rates:last week of June until the first week in September: $2,100/week Convenient To: Cape Cod Rail Trail, Conservation Area, Golf and Brewster beaches. A/C units in... View all property information
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    Brewster, Cape Cod 02631
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    419 Paines Creek, Brewster -(ID# 29143) 2017 Season! Condo Duplex only 2/10 of a mile to Paines Creek Beach on Cape Cod Bay. One bedroom, one bath with living room/ kitchen area, enclosed porch with futon provide additional living area. Patio out the back door with gas grill private wooded yard. NO... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    108 King Fisher Cartway Brewster MA (ID# 18141) ~Waterfront on Cape Cod Bay! 2017 Season! This charming and traditional waterfront home overlooks Cape Cod Bay! You will find panoramic waterviews, beautiful sunsets, and sunrises atop the sandcliffs that lead down to the property s own sandy beach.... View all property information
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    Brewster, Cape Cod 02631
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Waterfront on Cape Cod Bay! Absolutely fantastic beachfront home with private stairway down to its own sandy shore of Breakwater Beach on Cape Cod Bay. This exquisite property is ideal for the larger gathering offering four levels of living. Beautifully yet comfortably appointed throughout with... View all property information
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    Brewster, Cape Cod 02631
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Walk to Paines Creek Beach, Dog Friendly, Renovated Kitchen, AC 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 true delight... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    At this home you will great access to the bike trail through a neighborhood private access path that runs adjacent to the property and apprx. 1/2 mile to Crosby Beach. There are 3 bedrooms and 2.5 bathrooms, washer / dryer, 4 A/C units as well as a whole house fan, cable TV, WIFI internet access,... View all property information
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    Brewster, Cape Cod 02631
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    READY TO RENT FOR 2017 Street Level, King Bed, 2 ACs, 4 Pool Passes (Fees Apply) This is a lovely, 2 bedroom, 2 bath, apartment-style unit in Chilton Village that features a new king bed, new carpeting in the bedrooms, and solid flooring in the living area. The master bedroom offers a new... View all property information
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    Brewster, Cape Cod 02631
    1 / 14
    4 of 5 bubbles (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    51 Puritan Drive Brewster MA (ID# 49063) ~ Close to Beaches Spacious 4BR/2BA Cape style home close to Linnell Landing Beach on the bayside of Brewster! This home offers air conditioning, WIFI and convenience to beaches, bike trail, Nickerson State Park, antique shopping along picturesque Rt 6A and... View all property information
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    Brewster, Cape Cod 02631
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    139 Nelson St., Brewster -(ID# 95702) ~ Private Association Beach 2/10 mile This great vacation home is 2/10 of a mile to a private association beach on Cape Cod Bay! This quintessential beach cottage has distant views of Cape Cod Bay from the front yard, a great screened in porch, a wonderful... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Private beach access at just 1000 ft!! You are certain to enjoy your Cape Cod vacation at this beautiful 3+ bedroom, 2 bath Brewster home. This rental home is located just 2/10ths of a mile from private beach access to Ellis Landing Beach on Cape Cod bay. It is situated on a lovely, private,... View all property information
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    Brewster, Cape Cod 02631
    1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    READY TO RENT FOR 2017 Street Level, 1 AC This is a nicely decorated, well kept Fletcher Village apartment. The bedroom has a queen bed with a flatscreen TV and AC. The kitchen comes fully equipped; including a dishwasher and microwave. There is seating for 4 in the dining area. The living... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    This immaculate Brewster home sits directly on Upper Mill Pond, one of the largest kettle ponds on the Cape. Come and enjoy the beautiful view and great swimming right in back of the house! The winding stairway in back of the house will take you from the back yard, down to your own private dock.... View all property information
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    Brewster, Cape Cod
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    [~]This super private retreat is located on large and sunny lot with two outdoor living spaces: one functions as a summer kitchen with gas grill and patio dining set with umbrella; the other on the opposite side of the home features wicker furniture with cushions and two umbrellas for those who... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Beautiful, Comfortable home. 4/10ths to Ellis Landing, Cntrl AC and more! Beautiful, updated and very comfortable Cape Cod Summer Rental home ideal for families and larger groups. Come enjoy this fantastic location and renovated Cape in a private yet convenient location. Only 4/10ths to Ellis... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Ref # 379319 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Luxury condo located in Ocean Edge Resort and Golf Club. Available for winter months.... View all property information
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    Brewster, Cape Cod 02631
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    2 WEEKS MINIMUM. This charming two storied home sits atop a quiet driveway that leads directly to Mants Landing Beach on Cape Cod Bay. The house is nestled high on a knoll with sweeping views over the bay. A few steps down the driveway puts your feet into the sand. A very short drive takes you to... 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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    Paines Creek Beach!! The beautiful and comfortable Cape Cod vacation rental has 3 bedrooms & 2 full bathrooms. At this lovely Brewster rental home you can enjoy a spacious yard with a beautiful deck area. It is located just 1 mile to gorgeous Paines Creek beach on Cape Cod bay and 1 mile to... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Patio
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    • Satellite TV
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    • DVD Player
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    About this property
    165 Mill Pond Drive, Brewster MA (ID# 106329) ~ Mil Pond and Paines Creek Area 2017 Season! Lovely, like-new spacious Cape near the Mill Ponds in Brewster for fresh water sports including kayaking, canoeing, sailing fishing and swimming and about 2 miles to Paines Creek beach on Cape Cod Bay. Three... View all property information
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    Brewster, Cape Cod 02631
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    3 of 5 bubbles (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pet-friendly
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    READY TO RENT FOR 2017 Patio Style with Loft, Central AC, Remodeled Kitchen, WIFI & 6 Pool Passes (Fees Apply) This lovely Susanna Village patio home features central AC and has 2 bedrooms plus an open loft. The master bedroom is located on the main floor and has a queen bed plus a private... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Enjoy vacation in a homey ambiance, located just a short drive from Brewster's Bay beaches, ponds, golfing and the Cape Cod Rail Trail. The kitchen has been updated with new appliances and tile work and a colorfully furnished and decorated screened porch leads out to beautifully maintained lawns... View all property information
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    Brewster, Cape Cod
    1 / 22
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
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    $4950 PRIME SUMMER WEEKLY RATE Spacious home located near beach, golf and bike trail. This spacious and modern home is located less than a half mile from beautiful Crosby Landing Beach, some say Brewster's best. The home is a unique multi-level Tudor style home that provides multiple living areas... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Waterfront
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    Custom Beach House Directly on the Water, Sleeps 6 PRIME SUMMER WEEKLY RATE: $5,800-$6,200 Owners have replaced the original cottage on this property with a totally new, two-story vacation home. From its perfect perch above the Bay you have panoramic 180-degree water views. The steps down to the... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Outdoor Dining Area
    • Porch
    • Grill
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Classic Cape Cottage One House Back from Private Beach (062-BK) Peak Summer Weekly Rates: $2,200 - $2,400 Three day minimum stay available April 29 through June 3. Enjoy a bayside beach vacation in a timeless cottage tucked into the dunes near Ellis Landing. This classic cottage is a mere 15-... View all property information
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    Brewster, Cape Cod 02631
    1 / 37
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    Upscale Lake Front Home with Spectacular Views and Large Private Deck Peak Summer Weekly Rates: $4,600 - $4,800 If you love nature, privacy and water views this comfortable home is for you. You will wake up each morning to find the water sparkle over the pond with the unspoiled Punkhorn... View all property information
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    Brewster, Cape Cod 02631
    1 / 53
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Big, Updated Brewster Home, 2 Minutes to Beach $4,900 PRIME SUMMER WEEKLY RATE Please note: This property rents Sunday to Sunday. You will be on this home's perfect private association beach in less than a two-minute walk from the door. The home's exterior exudes traditional Cape Cod charm, while... View all property information
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    Brewster, Cape Cod 02631
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    Brewster Park, Stunning Bay Views, Perfect Sandy Beach, Kids Programs. Central Air, Pets Considered, Linens Provided. Prime Summer Weekly Rate: $4,700 - $4,900 Sample the unique Brewster Park family vacation experience. Delight in panoramic, elevated beach and bay views from your private deck. Walk... View all property information
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    Brewster, Cape Cod 02631
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • DVD Player
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    190 Paines Creek Road, Brewster, MA (ID# 80504) ~ Close to Paines Creek This ideal home, fully open and beautifully restored, boasts 3 bedrooms, including a private second floor master bedroom suite with Queen bed and bath, and two bedrooms on first floor, both with 2 twin beds and bath in the... View all property information
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    Brewster, Cape Cod 02631
    1 / 9
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    READY TO RENT FOR 2017 C-Style, King Bed, Straight Staircase, 3 ACs, 6 Pool Passes (Fees Apply) This is a lovely Howland Village townhouse that features a large, flat screen TV with Blu-ray DVD and available Netflix/Roku streaming. A straight staircase leads up to 2 air-conditioned bedrooms,... View all property information
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    Brewster, Cape Cod 02631
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Patio
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Shared Outdoor Pool...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
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    READY TO RENT FOR 2017 A-Style, Renovated, 3 Ductless ACs, WIFI & 6 Pool Passes (Fees Apply) This impeccably maintained and renovated Trevor Village townhome features ductless AC throughout. Guests will appreciate the central location and proximity to the Fletcher indoor and outdoor pools,... View all property information
    Location Information
    Brewster, Cape Cod 02631