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Holiday Rentals in Brewster, MA

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    All 367 Rentals in Brewster
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    Travellers to Brewster are booking June dates now. Secure your holiday home today, and have the perfect trip.
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    ₹44,555
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    1 / 9
    1 Bedroom / 1 Bathroom / Sleeps 4
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    ₹105,022
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    ₹185,539
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    ₹89,110
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Smoking allowed
    • Suitable for children
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    About this property
    Lovely home with decorative style comfortably sleeps eight. Location is perfect for biking on the Cape Code Rail Trail and exploring 22 miles of lovely Cape Cod from your bicycle. The house is also very close to several of the areas fresh water lakes and of course its just a short drive to the area... View all property information
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    ₹76,380
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    1 / 19
    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Private Setting, Short Drive to Pleasant Bay Beach, 5 ACs & WIFI - Located in a private setting, this 3 bedroom (sleeps 7), 3 bath home is minutes away from Pleasant Bay and Captains Golf Course. All the bedrooms are on the second floor. The master bedroom has a queen size bed, AC with private... View all property information
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    ₹63,650
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    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This is an exceptional, completely remodeled end unit. There is a central A/C unit located in the loft which cools the entire home but has no vents (see note below). You also have wireless internet, fully equipped kitchen with dishwasher, washer/dryer, open living room with TV and queen size sleep... View all property information
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    ₹70,015
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    1 / 12
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
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    About this property
    AFFORDABLE New 2015 Listing!! SHORT WALK TO POND! This 3 Bedroom, 1 bath home in a tranquil setting on a dead end street offers a great vacation rental opportunity! Located close to Punkhorn Park, Upper and Lower Mill ponds, enjoy hiking, swimming kayaking and more! Brewster beaches are just a... View all property information
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    ₹95,475
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    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This Brewster home, located in a quiet neighborhood, offers an open feel with cathedral ceilings in the livingroom and kitchen. The property offers three bedrooms, one with a king sized bed, one with a queen sized bed and the third with two bunkbeds, sleeping 8 comfortably. The property is also... View all property information
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    ₹95,475
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    1 / 19
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
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    About this property
    Newly listed! Lovingly and beautifully renovated 4 Bedroom, 2 Full bath home with central AC in the heart of Brewster, is the perfect getaway for your Cape Cod vacation! Located in the desirable Stonehenge neighborhood, this home has it all! Enter to the right of the entry into the bright and airy... View all property information
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    ₹127,299
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    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    NEW LISTING! Charming vacation home in a quiet neighborhood with pedestrian and biking access to abutting Nickerson State Park. Great location for hiking, biking, kayaking, swimming and fishing! Explore the nature trails to nearby Cliff Pond which is less than 1/2 mile away. This 3 bedroom ranch... View all property information
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    ₹44,555
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    1 / 21
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Indoor Pool
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
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    About this property
    Ocean Edge Resort - Nice 2 bedroom, 2 bath second floor unit on Eaton Lane with wireless internet, washer/dryer open living room & dining area with window A/C. Bedroom#1- 1 Queen; Bedroom #2 - 2 twins. Has a charcoal grill for use in back yard. Weekly Pool Pass cost to TENANT (at time of arrival to... View all property information
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    ₹38,190
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Dishwasher
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
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    About this property
    Street Level, Updated Kitchen, 1 AC & WIFI- This is a nicely decorated, Fletcher Village apartment. The bedroom has a queen bed, TV with DVD player, and AC. The updated kitchen comes fully equipped; including a dishwasher and microwave, and there is seating in the dining area. The living room... View all property information
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    ₹95,475
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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Ocean Edge with Pool Passes at tenant's cost! This is a nicely decorated 2 bedroom (sleeps 6), 2 bath home with wireless internet and wall a/c unit in the living room and upstairs bedroom. There is a fully equipped kitchen with dishwasher, living room, dining room and washer/dryer.---Weekly Pool... View all property information
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    ₹76,380
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • Suitable for children
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    About this property
    AC added for 2015! Charming 2BR/1BA cottage under half a mile to Linnell Landing Beach. This quintessential Cape Cod cottage is nicely decorated with living area/ kitchen area and two bedrooms that sleeps up to four. Enjoy the fresh Cape air or outdoor dining on the screened in porch. Very close to... View all property information
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    1 / 1
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Enjoy the Summer Breezes at this cul de sac location off Robbins Hill Road and only a 5 minute walk to a great sandy beach on Cape Cod Bay! Welcome to Cape Cod! Bring the whole family to this 3 bedroom 2 bathroom home that has many custom features: Fireplaced Living Room with 2 large sofa's (1 is a... View all property information
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    ₹133,664
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    1 / 17
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    A 3BR/2.5BA custom home offering a tranquil setting for a summer vacation with access to Sheep's Pond, close to Cape Cod Bay beaches, shopping, restaurants, golfing and entertainment. This bright, fresh, thoughtfully furnished and decorated home offers stylish multi-level living and is conveniently... View all property information
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    ₹127,299
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    1 / 10
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Short Walk to Beach with Waterviews: This is a contemporary “upside-down” style home with 4 bedrooms, 2 baths including wireless internet, washer/dryer, fully equipped kitchen, living room and dining area along with sliders from the living area to a nice deck where you can enjoy the sunsets over... View all property information
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    ₹70,015
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    1 / 15
    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Air Conditioning
    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    ID #HOL212 This Spacious Brewster 4 bedroom, 2 bath home is set in the Robinwood neighborhood abutting beautiful Nickerson State Park, located just in off Historic Route 6A. [~] There is access to a Fresh water swimming at Owl Pond. Also only a short drive (approx. 1.6 miles) to either Linnell... View all property information
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    ₹219,591
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    1 / 30
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
    • Grill
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Elegantly Renovated Cottage, 3 Minutes to Beach $3,200 PRIME SUMMER WEEKLY RATE Book July 4th Week, Stay an Extra Night at 50% Off! Please ask for details: 508 896-3241. Vacation at this upscale, elegantly renovated cottage, surrounded by 10 acres of Brewster Conservation Trust Land, yet only .125... View all property information
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    ₹98,657
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    1 / 7
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Ocean Edge Resort with pool passes at tenant's cost! - Comfortable 2 bedroom, 2 bath unit with wireless internet, washer/dryer, living room with A/C, dining area and kitchen .Weekly Pool Pass cost to TENANT (at time of arrival to Ocean Edge): $48per adult & $25 per child (under 12); Daily Pool... View all property information
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    ₹122,526
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Grill
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Breath taking view, you'll relax the minute you sit on the deck. Swim, boat, fish, and even waterski on Long Pond. And the beautiful Brewster bay beaches are only a short bike ride or drive away. Located on both Long and Black Ponds: This is a 2 bedrooms, 1 bath cottage offering wireless internet,... View all property information
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    ₹103,431
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Patio Style with Enclosed Loft, King Bed, Central AC, WIFI & 6 Pool Passes (Fees Apply) - This nicely decorated, patio home in Susanna Village features Central AC, a spacious open floor plan with newer carpeting/laminate flooring, new windows and slider, and a fully enclosed loft. There are 2... View all property information
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    ₹31,825
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    1 / 11
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This Unit will book fast don't delay!! Charming and bright studio on Greenland Pond! This quaint studio has its own private entrance is located on the second floor of a private home in a picturesque and secluded area overlooking Greenland Pond. It abuts conservation land, has access to a shared... View all property information
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    ₹76,380
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    1 / 15
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Only 2/10’s mile to Sheep Pond with Central A/C: This is a lovely 3 bedroom, 1 ½ bath home with a very short walk to private association beach on Sheep Pond, this home offers central A/C, washer/dryer, both wireless internet or cable access internet located in the living room near the bookshelves,... View all property information
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    1 / 13
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This A style townhome has many improvements and is quite luxurious! Located on the 9th Fairway with views. Split A/C to keep you cool and a gas fireplace for those cool evenings. Fully equipped with everything that you need to make your vacation a memorable one! If you are accustomed to the finer... View all property information
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    ₹445,548
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    1 / 36
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Waterfront on Paines Creek Beach, Stunning Bayside Views, Central AC, WIFI & Premium Cable Pkg. - Here is a spectacular, renovated and tastefully decorated, contemporary, 4+ bedroom, 4 bath home featuring panoramic views of Brewster's Paines Creek Beach. Imagine watching incredible sunsets... View all property information
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    ₹54,102
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Only 6/10’s mile to Private Sheep Pond Association Beach: This is a relaxing 3 bedroom, 2 bath ranch style home offering wireless internet, washer/dryer, ping pong table, fully equipped kitchen with new refrigerator and dishwasher, dining area, living room and sliders to deck and outside enclosed... View all property information
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    ₹85,927
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
    • Internet Access
    • Private Indoor Pool
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    Meticulous Eaton Village 2/BR unit with peeks of the golf course and lots of amenities. Spacious open floor plan with cathedral ceilings, two full baths, and wall ac unit. Pool passes are included but fees associated are NOT included. $100 Administrative Fee. Linen package for 6 available upon... View all property information
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    ₹76,380
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    1 / 14
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Grill
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Pet Friendly!! Ideally located in the heart of Brewster,close to Route 137, this property offers easy access to the Captains Golf Course, Biking Rail Trail and Brewster Beaches just a short drive away. This 3 bedroom and den, 2.5 bath home is quite affordable and a bargain waiting to be had!! This... View all property information
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    ₹197,314
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    1 / 31
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Private, Clean, Quiet - 3-Minute Walk to Beach$2,900 PRIME SUMMER WEEKLY RATE It's unusual to find this much privacy and seclusion so close to a beautiful Brewster beach - only a three-minute walk away. The cottage fronts on an unpaved cart way and is set back from the road on a large, nearly... View all property information
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    ₹63,650
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Secluded ranch set far back off the road in a wooded setting. This meticulous home offers newer furnishings throughout, air conditioning and all amenities. A nice location with easy access to the Cape Cod Rail Trail, Nickerson State Park and a short drive to the bayside beaches. Additional... View all property information
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    ₹54,102
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    1 / 10
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Grill
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Short Walk to Beach only 4/10’s mile away: This 2 bedroom, 1 bath cottage offers you an affordable and comfortable vacation with a fully equipped kitchen, living room, dining area, washer/dryer, deck and enclosed outside shower. This home is nestled at the end of a cul-de-sac surrounded by... View all property information
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    ₹79,562
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    1 / 6
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Shared Outdoor Pool...
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    About this property
    Sea Pines: 3 bedroom 2 bath condo located in Sea Pines. Short walk to the beach. There is a pool and tennis courts. Central A/C and washer/dryer. First Floor: Bedroom#1 - 1 King with full bath; Bedroom#2 - 1 Full; Loft: Bedroom #3 is an enclosed loft with 2 Twins. NO PHONE, NO INTERNET. 4 WEEK... View all property information
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    ₹76,380
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    1 / 10
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Grill
    • Internet Access
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    • Pets allowed
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    About this property
    AC for 2015!! Short walk to town bay beach too! Relax and enjoy this comfortable and affordable four bedroom. two bath home. Quiet location with porch and nice backyard. Max occp 10. 2 first floor bedrooms have 1 queen and 2 twins. 2 second floor bedrooms have 1 full and 3 twins. No A/C. Wireless... View all property information
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    ₹286,424
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    1 / 20
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    This expansive 5BR/3BA home is perfect for large groups or reunions. Just recently purchased this owner is fully committed to making your Cape Cod vacation a wonderful and memorable one. Recent upgrades will include new hardwood flooring in kitchen and living area, new interior paint, large flat... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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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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    ₹70,015
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    165 Mill Pond Drive 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 spacious bedrooms with master on the first floor with california king... View all property information
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    Just renovated historic Carriage House with waterview in the heart of Brewster's Main Street. Approximately 1 mile to Saint's Landing Beach and a short distance to General Store and churches. Galleries and antique stores nearby and short drive to Cape Cod Rail Trail for biking and hiking. This... View all property information
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    Short Walk to public town bay beach: Nicely decorated and furnished 3 bedrooms, 2 bath ranch style home with Central A/C, washer/dryer, wireless internet. Open living/dining room area with sliders to the deck with enclosed outside shower. Located on a quiet private road, direct TV includes NESN,... View all property information
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    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
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    ID #YANK408 Nice Landscaping, Granite Kitchen Counters and Tiled Baths. [~]This beautifully decorated Brewster Vacation home has many amenities to offer such as HIGH SPEED Internet access, HD TV's, multiple A/C units, brand new eco-friendly washer and dryer and Ocean Edge Resort amenity access... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Ocean Edge with Pool Passes at tenant's cost: This is a bright, meticulously maintained and nicely decorated 2 bedroom (sleeps 6), 2 bath condo unit located at the Ocean Edge with washer/dryer, wireless internet and some air conditioning. This home offers a wall a/c unit in only the master bedroom.... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Located at Ocean Edge Resort. This is a nicely decorated 2 bedroom, ½ bath condo with A/C units and TVs located in both the living room and master bedroom, fully equipped kitchen with dishwasher, dining area, living room (with A/C & TV), sliders to the patio. Starndard stairs to second Floor:... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    Lovely 2 Bedroom, 2 Bath Townhome at Sea Pines in Brewster. Located just steps form the private beach, this home is sure to please. The home boasts AC, Wifi and OCean Views from the upper deck. The lower deck features patio furniture and a gas grill. Bedroom #1 on the lower level has 1 Queen... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 7
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    Only 1/10th mile to Private Association Beach: This is a comfortable 3 bedroom (sleeps 7), 1 ½ bath summer cottage offering wireless internet, washer/dryer, fully equipped kitchen, dining area and living room with TV. There is also an enclosed front porch to view peaks of the Bay. Second Floor:... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Waterfront
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    Ava Maria - This 4 bedroom 2 bath summer cottage is lovingly called by the owner. Build in the 50 s with modern upgrades. Short walk down a path to a private assoaciation bay beach. Large grassy yard for little ones to run and games to play. Additional amenities include: coffee maker, smoke free,... View all property information
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    ₹159,124
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    Only 500 feet to shared private beach from this lovely 4 bedroom, 2 bath home offers, A/C, WIFI, washer/dryer and even and enclosed outside shower. Enjoy relaxing on the private deck and walk down to the beach after dinner so see some beautiful sunsets! First Floor: Bedroom #1 – 1 Queen with... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    Just 4 houses away from Private Association Beach: This 3 bedroom (sleeps 10), 2 bath home is considered an 'upside down' style home in which the living room, dining, kitchen and 2nd floor deck offer you views of the water, there is a washer/dryer, fully equipped kitchen, living room and dining... View all property information
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    ₹60,467
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    C-Style, Straight Staircase, WIFI & 4 Pool Passes (fees apply) - This Billington Village townhouse is a short walk to Arbor Pool and the Linx Tavern. The 2 bedrooms are upstairs, along with the full bath. The master bedroom has a queen bed, and a ceiling fan. The 2nd bedroom has 2 twin beds,... View all property information
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    ₹76,380
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    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Satellite TV
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    • Pets allowed
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    Patio Style with Loft, King Bed, 3 ACs, WIFI & 8 Pool Passes (fees apply) - This patio style home in Susanna Village includes an open loft bedroom, all new windows and doors, and new tile throughout the entire main floor including the bedrooms. The master bedroom on the main floor features a... View all property information
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