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Brewster Luxury Vacation Rentals

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    Travellers to Brewster are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    38 Matching Rentals in BrewsterView all 259 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    4 minute walk to one of Brewster's best beaches! Stunning brand new 5 bedroom, 4.5 bath custom home with in-ground Salt Water Swimming Pool close to Point of Rocks Beach in Brewster. Air conditioning throughout. Large open first floor living. Gourmet kitchen has breakfast bar with 6 stools. Dining...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    LARGE Waterfront on Paines Creek Beach, Stunning Bayside Views, Central AC **Greatly Reduced Week 8/18-8/25 *** Here is a spectacular, renovated and tastefully decorated, contemporary, 4+ bedroom, 4 bath home sleeeping 12 featuring panoramic views of Brewster's Paines Creek Beach offering six...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2 WEEKS MINIMUM. This charming two storied home sits atop a quiet driveway that leads directly to Mants Landing Beach on Cape Cod Bay. The house is nestled high on a knoll with sweeping views over the bay. A few steps down the driveway puts your feet into the sand. A very short drive takes you...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Large, recently renovated home, right on the beach in Brewster. $6,900 PRIME SUMMER WEEKLY RATE  (Saturday to Saturday rental only) Tucked out of sight from the unpaved cart way that runs by it, this expansive 5 bedroom home is situated directly on the beach on nearly an acre of privacy in an...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    108 King Fisher Cartway Brewster MA (ID# 18141) ~Waterfront on Cape Cod Bay! 2018 Season! This charming and traditional waterfront home overlooks Cape Cod Bay! You will find panoramic waterviews, beautiful sunsets, and sunrises atop the sandcliffs that lead down to the property s own sandy beach....
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Custom, Upscale, Taste & Style - Paines Creek Beach Brewster (Linens included) Peak Summer Weekly Rates: $6,400 - $6,800 Rents Saturday to Saturday during peak season This beautiful custom home is located near Paines Creek Beach, in fact there is only one home between you and the beach. The owner...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Private Pool & 4 Bedroom, 2 bath, 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 private salted (unheated) swimming pool, association tennis court, shuffle board, & horseshoe pit,...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Impeccable Vacation Home, 200 Feet from Beach. Peak Summer Weekly Rates: $4,800 - $5,000 Rents Saturday to Saturday This is an immaculate and beautifully decorated 3 bedroom, 2 ½ bath home about 200' from a private association beach in the Ellis Landing neighborhood in Brewster. There is central...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    This stunning, nicely renovated Brewster home is located just 1/2 of a mile to beautiful Crosby Beach and just 1/10th of a mile to the bike trail at Nickerson State Park. There are 6+ lovely bedrooms & 5 full and 1 half bathrooms. The gorgeous kitchen is equipped with all of the needed cooking...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Bright, Fresh, Airy, Comfortable, One Minute Walk to Private Brewster Neighborhood Beach  Peak Summer Weekly Rate: $4,800 Rents Sunday to Sunday About as close to the water as you can be without being directly on it. Walk out the front door and straight ahead to a short, shaded path and your...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Loads of Living Space, Water Views at Brewster Home by the Bay Peak Summer Weekly Rates:  $6,800 - $6,950 Rents Sunday to Sunday Linens not included Please click on the 'Virtual Tour' to see a 3D tour of the home This beautiful house was built in 2007 and includes all the modern amenities:...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Brand New and Right on the Beach, Sleeps 8 Peak Summer Weekly Rates:  $7,600 - $8,000 Rents Saturday to Saturday   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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Perfect for a large group! This fantastic large waterfront home is nestled on Upper Mill Pond in Brewster. Upper Mill Pond is one of the cleanest swimmable ponds on the Cape and perfect for all non-motorized water activities such as SUP-stand up paddle-boarding, kayaking, canoeing, etc. The...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    VACATION IN LATE AUGUST, SAVE $800 OFF PRIME SUMMER RATE! AUGUST 24-31 NOW AVAILABLE AT $4,900! Please note: This property rents Sunday to Sunday. It has a beautiful location, right on a private sandy neighborhood beach. The yard and screened porch facing the Bay are extremely private and...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cheery Cape Beach Cottage Directly on Cape Cod Bay Peak Summer Weekly Rates: $3,900 - $4,000 Rents Saturday to Saturday A classic, yet updated Cape Cod cottage, directly on a perfect sandy, private association beach. There is 450 feet of beach front, with private access from only 13 cottages...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Custom Built New Home, Three Minutes To Beach Prime Summer Weekly Rates: $5,200 - $5,400 Rents Sunday to Sunday It's a custom built home in the Ellis Landing Beach section of East Brewster with a three-minute walk to a private, neighborhood beach.   The house is a gem, maintained in tip-top shape...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Bay Views and Short Walk to Grandfather's Beach, Central AC Take in the stunning sunsets from the spacious deck of this 4 bedroom, 3 bath home that overlooks Cape Cod Bay and is located steps away from Grandfather's Beach in Brewster (a private association beach). This spacious home offers...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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,...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Directly on Sheep Pond, Brewster, Private Sandy Beach, Sleeps 12 Linens and Beach Towels Included Peak Summer Weekly Rates: $6,900 - $7,200 NEW Listing for 2018!   This is the perfect vacation headquarters for your multi-generational or multi-family group. You are privately and ideally situated...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Walk to Brewster's beautiful Crosby Landing Beach, one of Cape Cod's most desirable bay beaches from this spacious, stylish, and privately situated home. Attractively furnished, impeccably maintained and fully equipped, this 3-BR, 2-Bath ranch sleeps six-to-nine. It is configured to happily...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    New Listing for 2018! Brand New Custom Brewster Home with Heated Pool, 4 Min Walk to Private Beach Sleeps 10, Linens Included Rents Saturday to Saturday Be among the first guests in this brand new home!  The house is located on a HUGE lot with a private in ground pool. In addition, the house is...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Renovated Beauty on the Beach in Brewster Peak Summer Weekly Rate:  $5,900 Rents Saturday to Saturday The property is as close to the water as you can get! 4 steps from the main level deck brings you to the private stairs down to the private beach only shared by 3 other homes. Cape Cod Bay...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Water views, 150 feet to private beach Peak Summer Weekly Rates:  $3500 to $4500 Rents Saturday to Saturday during peak season It's a two-story vacation home with wonderful views of Cape Cod Bay from practically every room. The family room is on the second floor to take maximum advantage of the...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Dramatic six-level contemporary home with association access to the freshwater of Blueberry Pond-- just two-tenths of a mile to The Cape Rail Trail. A great room with cathedral ceiling, skylights and hardwood flooring is located at the top level to take advantage of the panoramic view of Cape Cod...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Charming Beach Front Cottage on Pvt Beach1 / 12
    (5)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Reviewed August 26, 2017
    I paid a premium price to have a place on the beach and to be able to see the beach and ocean. My view from the deck was totally obstructed by overgrown plants. It was clear...
    Reviewed November 10, 2016
    Vacation was good but still have not received refund of $200 per agreement with owner who claimed that he was entitled to half of the $400 deposit I put down for any damage. Can...
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    Waterfront on Cape Cod Bay! Completely renovated beach front cottage with gorgeous views and amazing sunsets. Private stairway to the beach to put your toes right in the sand. Exquisite details inside include hardwood floors and fully equipped Kitchen. The space is perfect for entertaining with the...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    This quintessential beach cottage has views of Cape Cod Bay from the front yard. Gorgeous vacation home just .1 mile to a private association beach on Cape Cod Bay! You will love the screened in porch, a wonderful outside shower, and a simply relaxing and charming atmosphere. Home has 4 large...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Rights to Brewster's Best Private Beach1 / 14
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful renovated home with all the amenities. Stainless steel appliances, lovely furnishings, master bath with whirlpool tub and separate shower. The separate guest suite has 2 bedrooms, one with a double bed and one with two twins. They shore a common bath. The yard is very private, level...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Custom Beach House Directly on the Water Prime Summer Weekly Rates:  $5,800-$6,200 Rents Saturday to Saturday 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Street Level, Golf Access, King Bed, Renovated, 4 ACs, 6 Golf & Pool Passes (Fees Apply) Ready to Rent for the 2018 Season 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...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    GOLF & POOL: Updated Street Level, 3 BR, 3 Bath, 3 ACs, 8 Passess (Fees Apply) Ready to Rent for the 2018 Season Now featuring GOLF ACCESS and RENOVATED further for 2018! This spacious 1600 sq ft, Endicott Village condo has been renovated, updated, refreshed and is well decorated. The condo...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Spectacular Beach Front Home on Cape Cod Bay1 / 12
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed August 30, 2016
    This cottage had it all for us. Amazing sunsets, beautiful beach, great location!And a dishwasher. What more could I ask for!
    Reviewed June 2, 2016
    We love this house! Perfect - house is comfortable, well maintained, spectacular setting. Loved the incredible view over Cape Cod Bay, walks along the beach, watching the oyster...
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    About this property
    Located atop the dunes overlooking Cape Cod Bay in Brewster MA this amazing home is the answer to your vacation wish list. Recent renovations include new washer/dryer, fresh paint, new décor and linens, wireless internet and cable. Weeks still available in July, August and September. You will enjoy...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Breathtaking Views Directly On Sandy Beach Now with air conditioning! SAVE $400/WEEK FOR AUGUST 26 WEEK ONLY!  SEE REDUCED RATE LISTED. Rents Sunday to Sunday This family beach house is directly on a private, sandy beach in Brewster – one of the best beaches on the Bay. The house is ideally...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Walk to Brewster Beach, Sleeps 10 with In-Law Apartment Peak Summer Weekly Rates:  $4,950 - $5,500 Rents Saturday to Saturday Linens Included NEW listing for 2018! This four-bedroom home is perfect for your multi-generational or two-family group, and it's just a two-minute walk to one of the...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated, Light & Bright Brewster Beachfront Property Peak Summer Weekly Rates: $5,900 - $6,300 Rents Saturday to Saturday   A beach cottage overlooking a private, sandy, neighborhood beach in Brewster.  Panoramic views of Cape Cod Bay are maximized from the open deck and main living space.  The...
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    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 3 bedroom, 2 bath home is located down a lovely road, approximately 500 feet to a private Cape Cod Bay beach at the end of desirable Nelson St. There are restaurants within 4/10ths of a mile on 6A with JTs seafood, Brewster House of Pizza and more. This home is situated in a...
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    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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