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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.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    100 Pilots Way, Brewster MA (ID#121126) ~Pineland Park Association Beach 2017 Season! 1920’s classic bungalow, completely modernized and now air conditioned! Gem of the neighborhood in Pineland Park. Less than 1/10-mile to the beach! Three bedrooms, 1 1/2 baths, New 42” flat screen HD TV updated... 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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    Patio Style with Full 2nd Floor, Straight Staircase, Central AC, WIFI & 6 Pool Passes (Fees Apply) This free standing patio home (maximum of 6 people) in Susanna Village was renovated in 2014 to offer a full second floor with a 3rd bedroom and bonus sitting area. It features Central AC and a... View all property information
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    Brewster, Cape Cod 02631
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    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A-Style, King Bed, Renovated, 2 ACs, 6 Pool Passes (Fees Apply) This beautiful townhouse in Billington Village features a renovated kitchen, Pergo flooring in the living/dining area, renovated bathrooms, and wooded views. The master bedroom is up the spiral staircase and offers a king bed,... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A-Style, 3 Ductless ACs, 2 Queen Beds, WIFI & 6 Pool Passes (Fees Apply) This nicely decorated and well maintained, Trevor Village townhome features 3 Ductless AC units throughout. Guests will appreciate the central location and proximity to the Fletcher indoor and outdoor pools, tennis courts,... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Waterfront on Paines Creek Beach, Stunning Bayside Views, Central AC, 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 from the... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    B-Style, Renovated, Straight Staircase, 3 ACs, 6 Pool Passes (Fees Apply) This tastefully renovated townhouse is located in a private area at the end of Billington Village. It features hardwood floors, a beautifully renovated kitchen and dining area, and a living room with a 65" 3-D, flat screen... View all property information
    Location Information
    Brewster, Cape Cod 02631
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Upper Level, Renovated Kitchen, 2 ACs & 5 pool passes (fees apply) This Eaton Village apartment has comfortable decor and a recently renovated kitchen with newer appliances. The master bedroom has a queen bed, ceiling fan, AC, TV with DVD/VCR, and a private bath. The 2nd bedroom has 2 twin... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    Walk to Linnell Landing Beach & Bike Path, Central AC This cute 3 bedroom cottage is walking distance from beautiful Linnell Landing beach (0.3 mi). It had a major renovation in 2012; including kitchen upgrades, the addition of a Central AC system, and a bathroom renovation featuring a 4 ft x 4... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Private Saltwater Pool, King Bed, Association Tennis, Bike Path This modern, 4 bedroom, 2 bath, split-level home is located in the desirable Seaview neighborhood of Brewster where you can enjoy the association tennis court, shuffle board, & horseshoe pit, and have direct access to the Cape Cod... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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, tennis courts, and fitness... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A-Style, King Bed, Split System AC, WIFI & 6 Pool Passes (Fees Apply) This bright and sunny, Howland Village townhouse has all the comforts of home. Up the spiral staircase, you'll find the master bedroom with a king bed, TV/DVD player, AC & a ceiling fan, with a private bath. The adjoining... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A-Style, 3 ACs & 6 Pool Passes (Fees Apply) This 2 bedroom plus an open loft, Billington Village unit features stainless appliances in the kitchen and ductless AC in both bedrooms and the loft. The master bedroom is located on the second floor and offers a queen bed, ductless AC, flat screen... 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
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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
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    C-Style, Straight Staircase, 2 ACs & 6 Pool Passes (fees apply) This is a nicely decorated Billington Village townhouse. The main floor features an air-conditioned living room with comfortable seating, a flatscreen TV, and a sleep sofa; a fully equipped kitchen with new tile flooring and all... 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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    Close to Seymour Pond & Bike Path, Central AC Located in a nice family friendly neighborhood, this 3 bedroom, 2 bath home is situated just minutes away from Seymour Pond & the Cape Cod Bike Trail. Seymour Pond is swimmable. All the bedrooms are on the first floor. The master bedroom has a... 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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    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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    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    C-Style, Straight Staircase, Close to Fletcher Pools, 3 Ductless AC's, WIFI & 6 Pool Passes (Fees Apply) Located close to the Fletcher pools, tennis & basketball courts, this Trevior village townhouse features a very comfortable living area and golf course views. A straight staircase leads to... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Superb Bay Views, Walk to Paine's Creek Beach, AC, Pets Considered Peak Summer Weekly Rate: $3,800 - $4,100 Hidden away at the end of a dead-end road on the way to Paine's Creek Beach in Brewster, you'll find this cheery, appealing property built for the ideal Cape Cod family summer vacation. It's... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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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, 2 Bathrooms, Sleeps 8 | Quick View
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    Patio Style with Loft, King Bed, 3 ACs, WIFI & 8 Pool Passes (fees apply) This patio style home sleeping 8 is located in Susanna Village features tile flooring throughout the entire main floor, an open loft bedroom, updated windows and doors, and beautiful golf course views. The master bedroom... View all property information
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    Brewster, Cape Cod
    1 / 37
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A-Style, 2 ACs, 6 Pool Passes (Fees Apply) This Howland Village townhouse is located in a private setting. The first floor master bedroom has a queen bed and a flat screen TV. Up the spiral staircase, you will find the 2nd bedroom which offers 2 twin beds, AC, TV and a private bath. 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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    C-Style, King Bed, Updated, Straight Staircase, 2 ACs, WIFI & 6 Pool Passes (fees apply) This townhome in Howland Village has it all... an inviting private patio, charming decor, and a wonderful location close to the Fletcher Pool and Tennis Complexes and the Cardio Room. The nautical, "beachy"... 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
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    3 of 5 bubbles (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 bath. The 2nd bedroom has... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Street Level, King Bed, 2 ACs, 4 Pool Passes (Fees Apply) No need to climb stairs to access this street level, 2 bedroom, 2 full bath, Eaton Village apartment. This recently painted unit offers a master bedroom with a king bed, AC, TV, and a private bath. The 2nd bedroom has 2 twin beds,... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    B-Style, 2 King Beds, Straight Staircase, Enclosed Loft, 3 ACs & 6 Pool Passes (Fees Apply) This Billington Village townhouse features an enclosed loft accessed by a straight staircase, and laminate wood flooring throughout the kitchen and living room. The master bedroom is located on the first... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    B-Style, King Bed, Renovated, 2 Ductless ACs & 6 Pool Passes (Fees Apply) This bright and airy, freshly painted & renovated townhouse is located close to the entrance of Billington Village, so it is a short stroll to the Linx Tavern and Arbor Pool. It features 2 ductless AC units to cool the... 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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    Upper Level, King Bed, Updated, 4 ACs, 8 Pool Passes (Fees Apply) This updated and well decorated, 3 bedroom, 2 bath, luxury condominium has 1500 sq ft of living space, three private decks and spectacular golf course views! The Arbor Pool and Linx Tavern Restaurant are just steps away. Updates... 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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    C-Style, Updated, King Bed, Straight Staircase, 2 ACs, WIFI & 4 Pool Passes (fees apply) This newly updated, traditional townhouse unit in Howland Village has been a favorite for guests and recently had the bathrooms renovated. The new kitchen granite counter tops and the Pottery Barn accents... 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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    Street Level, King Bed, 4 ACs, 8 Pool Passes (Fees Apply) This spacious Endicott Village apartment is located in a wooded area and is a short walk to the Arbor Pool, Linx Tavern restaurant, and the tennis, basketball and volleyball courts. The master bedroom has a king bed, AC, TV and a... View all property information
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    Brewster, Cape Cod 02631
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Spend your vacation time at the Cape's most relaxing and peaceful luxury rental home. Our Barn is a romantic, 2nd-floor (~2000 sq ft) one or two bedroom, open, loft-style property. It is self-catered. We call it a Barn - but as you'll see from the pictures below - it is a warm, well-designed and... View all property information
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    Brewster, Cape Cod 02631
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Street Level, Golf Access, King Bed, Renovated, 4 ACs, 6 Golf & Pool Passes (Fees Apply) This is a beautifully decorated and fully renovated 3 bedroom, 3 full bath, Endicott Village, luxury apartment that is sure to please. This 1600sf unit overlooks the 9th fairway and green and, as a bonus,... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
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    Brand New, Upscale, Saltwater Views, 3 Minute Walk to Beach (Pets Considered) Peak Summer Weekly Rates: $5,800 - $6,200 (Sunday - Sunday rental) Built in 2015, this brand new home with central air-conditioning throughout is located in the Ellis Landing Beach section of East Brewster with a... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
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    • x
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    Classic Brewster Cottage Steps from Private Beach, Water Views, Pets Considered. Prime Summer Weekly Rate: $2,900-$3,200/week A classic Brewster cottage perched overlooking Cape Cod Bay, this property is an ideal beach retreat. The large open yard is unusual to find this close to the bay. Tons of... View all property information
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    Brewster, Cape Cod 02631
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    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    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, a full bathroom and the... View all property information
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    Brewster, Cape Cod 02631
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Ocean Views
    • Shared Outdoor Pool...
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Look at the bay from the upper floor deck in this Sea Pines town home. Community has a private beach,tennis courts and outdoor pool. Close to golf courses (3 within 10 miles) and ocean Property wifi ready and in an ideal location 200 paces to the water! 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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    • x
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    • x
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    Comfort & Convenience in the Heart of Brewster Peak Weekly Summer Rates: $2,500 - $2,700 This modern comfortable home is located in the heart Brewster, close to the beach, biking and several restaurants. Nestled in a quiet neighborhood just south of Route 6A, the home has 3 bedrooms: a master with... View all property information
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    Brewster, Cape Cod 02631
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Patio Style w/ Enclosed Loft, Renovated, Central AC, 6 Pool Passes (Fees Apply) This nicely decorated and renovated, Allerton Village home features recently updated central AC and an enclosed loft that serves as a third bedroom. The first floor, master bedroom has a queen bed, TV with DVD player,... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Central Heating
    • Wi-Fi
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    • Private Outdoor...
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    • Secure Parking
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    • Pet-friendly
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    • x
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    • x
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    This is a comfortable, casual home for easy summer living. The open first floor living area combines, kitchen, living and dining rooms, sun room, and music room with direct access to an expansive deck and steps down to the in ground private pool. A separate family room off the kitchen offers... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Air Conditioning
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Custom, Upscale, Taste & Style - Paines Creek Beach Brewster (Linens included) Peak Summer Weekly Rates: $6,400 - $6,800 This beautiful custom home is located near Paines Creek Beach, in fact there is only one home between you and the beach. The owner has done a spectacular job of decorating and... View all property information
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    Brewster, Cape Cod 02631
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A-Style, 3 Ductless AC's, WIFI & 6 Pool Passes (Fees Apply) This is a nicely decorated and well maintained Trevor Village townhome. Guests will appreciate the central location and proximity to the Fletcher indoor and outdoor pools, tennis courts, and fitness room. The master bedroom is located... View all property information
    Location Information
    Brewster, Cape Cod 02631
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
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    • ?
    • ?
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    • ?
    About this property
    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
    Location Information
    Brewster, Cape Cod
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Washer
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    125 Bog Pond Road (ID #133097) ~ Bayside four Bedroom Home ~ Brewster 2017 Season! This is a spacious open and bright home set in a private location in Brewster. This newly renovated 4 BR/2 BA home has hardwood flooring, updated furnishings & has been freshly painted. There is an open living and... 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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    • Grill
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    • DVD Player
    • Shared Outdoor Pool...
    • Satellite TV
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Brewster, Cape Cod 02631