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Holiday Rentals and Homes in Brewster, MA

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    All 233 Rentals in Brewster
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    €920
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    €1,288
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    3 Bedrooms / 1 Bathroom / Sleeps 7
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    About this property
    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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    1 / 24
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
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    • Pets allowed
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    About this property
    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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    1 / 10
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • 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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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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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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    About this property
    New 2015 Listing! Enjoy all the Cape has to offer with this Ocean Edge Resort Townhome! This 2 bedroom, 1.5 bath is situated on Fletcher Lane in the heart of the resort. The pools, tennis courts and small fitness center are just a short walk away! The main floor of the townhome comes with a half... View all property information
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    1 / 15
    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 Town Beach: Charming 4 bedroom, 2 bath home offering wireless internet, washer/dryer, fully equipped modern kitchen with dishwasher, living room with TV, dining area, lovely deck with an enclosed outside shower. First Floor: Bedroom #1 – 1 Queen, Bedroom #2 – 1 Full; Second Floor:... View all property information
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    €1,794
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    NEW 2015 Listing! **Rent any two consecutive or more weeks and receive a FREE beach pass reimbursement AND $100 OFF per week!! Take advantage of this sale while it lasts! From the minute you see the front deck's porch swing, to it's location and landscaping, you will fall in love with this... View all property information
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
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    About this property
    Unit# BRIE84 Terrific & Private Brewster, MA Vacation home near Saints Landing Beach and Historic Route 6A. [~]This much loved custom 2 bedroom Cape style home is located down a long winding private lane and has a very welcoming presence. Features include Central Air conditioning, wide plank... View all property information
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    €644
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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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    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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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    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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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Swim, fish, boat (motor boats included) in the biggest fresh water lake on Cape Cod. And still have a short drive to Brewster's beautiful bay side beaches. This wonderful home with exquisite views has Ductless Split system AC and 3 bedrooms and 2 baths. The home has a bright open floor plan with... View all property information
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    €4,507
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    1 / 11
    4 Bedrooms / 3 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
    Waterview overlooking Cape Cod Bay and 2 houses to Shared Private Association Beach. This large 4 bedroom, 3 bath home offers Central A/C, Wireless Internet, washer/dryer, comfortable living room, sunroom with door to deck, eat-in kitchen. First Floor: Bedroom #1 – 1 Queen; Bedroom #2 – 2 Twins;... View all property information
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    €1,173
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    1 / 8
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Dishwasher
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    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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    €1,840
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    1 / 18
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    139 Nelson St., Brewster -Property ID: 95702 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 outside shower, and a simply... View all property information
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    €1,012
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    1 / 12
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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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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    €2,483
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    1 / 9
    4 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Dishwasher
    • Grill
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Ahhh, enjoy the sights and sounds of the surf overlooking Cape Cod Bay and only few steps to a shared Private Beach! This is a wonderful 4 bedroom (sleeps 7), 3 bath home that offers all the best of Cape Cod at an affordable price! The home boasts wireless internet, some A/C, spacious and open... View all property information
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    €920
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    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • 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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    1 / 8
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    Wonderful Ocean Edge condo with A/C and access to the great pool club at the resort (pool passes at the cost to guest): This is a bright and nicely decorated 2 bedroom, 1 ½ bath townhouse style condo with A/C units located in the main lving area and master bedroom only. This unit has a fully... View all property information
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    €1,564
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    1 / 9
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This bright and spacious private home is located in the Heart of Brewster is a bargain, just off Route 6A is priced to rent! The home features central a/c, WiFi, fully equipped kitchen and a three-season porch. Just a short drive to Point of Rocks or Breakwater Beaches, this home is ideal for the... View all property information
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    €2,208
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    1 / 10
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
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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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    €1,633
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    1 / 12
    3 Bedrooms / 2 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
    Short Walk (4/10's mile) to public Point of Rocks Beach on the Bay: This is a comfortable 3 bedroom, 2 bath home offering air conditioning in all the rooms. Located in a quiet area you have it all with wireless internet, dishwasher, washer/dryer, deck along with an enclosed outside shower. The... View all property information
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • 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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    €1,771
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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
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    • 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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    €2,024
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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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
    Short walk to beach: Less than ½ mile to public bay beach and near State Park . Nice and comfortable 3 bedrooms, 2 bath home, with A/C, wireless internet and occupancy of 8 with sleep sofa - First Floor: New kitchen, open dining/living room, Bedroom #1 - 1 King with bath. Second Floor: family room... View all property information
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    €1,150
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    1 / 6
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Grill
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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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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    €1,472
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    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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 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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    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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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 Private Association Bay Beach: This is really a cozy and neat 3 bedroom with AC (sleeps 7), 2 bath home located on a quiet lane. This home offers you internet (WIFI), well equipped kitchen with dishwasher, open living room and dining area, washer/dryer and enclosed outside shower. All... View all property information
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    €690
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
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    About this property
    419 Paines Creek, Brewster -Property ID: 29143 Old fashioned summer-time duplex condo 2/10 of a mile to Paines Creek Beach. One bedroom, one bath with living room/ kitchen area, sleeping porch and patio off of the back provide additional living area. Modern amenities, but the charm is there. NO... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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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
    Ocean Edge Resort Condominium: Delightfully decorated 2 bedroom (sleeps 5), 2 bath condo with Central A/C overlooking the golf course. This quiet location is at the end of the street and seconds from the Cape Cod Rail Trail Bike Path - it couldn't be easier to access the 22 miles of bike trails.... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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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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    About this property
    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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    1 / 9
    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
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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 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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    3 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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    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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    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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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
    Short walk to a private path to Cape Cod Bay. Extensive renovations make this home the perfect place for your vacation. This classic summer home sits at the end of a sandy lane. Updated from stem to stern this great home has 5 bedroom, 2 full baths, Internet, outdoor shower, large back deck,... View all property information
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    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
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    • Satellite TV
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    • Pets allowed
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    About this property
    Property ID: 116159 / Key #: 9348 / Property Name: 116 King Philip Road Sparkling 3 bedroom home near the bike trail, bay beaches and Nickerson State Park. The house features central A/C with a bright sunroom overlooking the back yard, deck and outdoor shower. The living room has a gas fireplace... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Dishwasher
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    About this property
    Roomy, Bright Home 4 Minute Walk to Beach$4,500 PRIME SUMMER WEEKLY RATE Please note: This property rents Sunday to Sunday. The house is in the Ellis Beach Landing neighborhood of East Brewster and is a four-minute walk to a private, neighborhood association beach. The house has 4 bedrooms, two... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
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    About this property
    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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    5 Bedrooms / 2 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Pets allowed
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    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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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
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    • Pets allowed
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    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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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Dishwasher
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    About this property
    Short Walk to Private Association Bay Beach: This is a large and open 5 bedroom, 3 bath home with A/C in the 3 upstairs bedrooms, garage, wireless internet, washer/dryer, living room (A/C), dining area, deck overlooking the bay, located on a quiet street and just a short walk away to the... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Handsome 4-BR Home Near Crosby Landing Beach$4,200 PRIME SUMMER WEEKLY RATE An 8-10 minute walk from this big and neat-as-a-pin two-story home brings you to sweeping Crosby Landing Beach, considered Brewster's best by many. It's a beautiful sandy, bay beach with gentle waves for younger children.... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Walk to the pond to your shared private beach: This is a very pleasant 3 bedroom, 2 bath home that offers a country kitchen with dishwasher, washer/dryer, very nice den, secluded deck with an enclosed outside shower. All the bedrooms are on the first floor: Bedroom #1 – 1 Full, Bedroom #2 – 2 Twins... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Dishwasher
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    • Internet Access
    • Shared Outdoor Pool...
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    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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    €1,012
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    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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    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Grill
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    About this property
    AC for 2015!! This lovely 2 Bedroom 1.5 bath home just minutes from the beach! This affordable home boasts sleeping for up to 8 people, has Wifi and flat screen TVs in all the bedrooms as well as the living room. The inviting patio is perfect for those Cape Summer days and has a gas grill and... View all property information
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    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Balcony
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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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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
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    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Cottage Charm with Updates, 2 Minutes to Beach.$3,800 PRIME SUMMER WEEKLY RATE While trees do not permit a view of the Bay, you are very, very close here -- less than two minutes walk to the beach. Beach chairs provided. And it's one of the very best, private sandy beaches in Brewster. The owner... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Dishwasher
    • Grill
    • Satellite TV
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Upscale, 200 feet from private beach $4750 -- Peak Summer Rates (Linens Included) Book July 4th Week -- Stay an Extra Night FREE! Please ask for details: 508 896-3241 This is a newer beach house built in 2005. It is a 3 bedroom, 2 ½ bath home about 200' from a private association beach in the Ellis... View all property information
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