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Vacation Rentals and Cottages in Brewster, MA

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    1 / 38
    5 of 5 stars (5) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sleeps 6, Private Patio with Grill, option to purchase Pool and Sports passes Purchase of up to 6 pool and sports passes are available with this property. Please see bottom of the listing for details. This is a clean, family-friendly two-floor, 2 bedroom, 1.5 bath townhouse located in private... View all property information
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    Brewster, Cape Cod 02631
    1 / 23
    4.5 of 5 stars (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Very close to the beach for family fun! This magical 4 bedroom 2 bathroom home on a quiet cul-de-sac on Cape Cod in the Sea Captains' town of Brewster. Close to everything including directly across the street from Nickerson State Park and the bike trail. Enjoy lazy summer days in the sun or long... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed 3 days ago
    The house was spacious, clean, and perfect for a family get together. Everything we needed was provided, the host was responsive and welcoming. The location was perfect! An easy...
    5 of 5 stars Reviewed August 27, 2015
    Very nice property. Location is excellent, quiet end of cul-de-sac, 10 minute walk to very nice beach, easy access to Rte 6A and all that Brewster has to offer. Very near state...
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    1 / 29
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    STEPS TO SAINT'S LANDING BEACH, BREWSTER Privacy and seclusion close to a beautiful Brewster beach...the cottage fronts on an unpaved lane and has conservation land behind it. A 2-minute walk via the lane/sandy path or via the paved road takes you to Saint's Landing beach, a beautiful beach on... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed September 7, 2015
    My family and I were so happy that this home had all of the charm and quaintness we had hoped to find. It is located on a very quiet street. Décor was up to date/new and we...
    5 of 5 stars Reviewed August 18, 2014
    We had such an amazing time. The house was better than expected. We had 5 kids with us and the house was sooo accommodating. The house was clean, roomy, had everything we...
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    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    For rent is a 4 bedroom oceanfront house in Brewster, MA. The high tide mark is about 40 feet from face of house, no obstructions or trees to the view. Brewster is the site on the Cape where the tide goes out almost a mile at dead low tide. This exposes sandbars and tide pools which are great fun... View all property information
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    Brewster, Cape Cod 02631
    1 / 24
    5 of 5 stars (9) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located in quiet west Brewster among the pines, this newly renovated vacation home can sleep up to six people. It has a comfortable living/dining area with gas fireplace and cable TV, a fully furnished kitchen, a study (or baby's room), laundry, screened porch, and outdoor decks on each level... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed August 24, 2015
    The home was beautiful, had all the amenities, and Cheryl was knowledgeable and helpful about the area. We would definitely recommend it to others.
    5 of 5 stars Reviewed July 19, 2015
    This beautiful home is absolutely perfect for an escape. It was so clean, comfortable and fully stocked. We really could have cut back on much of our packing. Plenty of room for...
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    1 / 30
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Have a luxury vacation at our Home at the Ocean Edge Resort in Brewster on Cape Cod. Tailor your vacation to meet your needs with No REALTOR Fees. You can stay a minimum of 3 days not the usual 7. Quiet setting without the traffic of main entrance. What makes us unique? Our unit is unattached :... View all property information
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    Brewster, Cape Cod 02631
    1 / 12
    5 of 5 stars (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    24 Old North Road, Brewster MA ~ Firndale Cottage ~ (ID# 21525) Close to Bay Beaches Known as "Firdale Cottage," this lovely Cottage is 7/10ths of a mile to Point of Rocks Beach. Close-by are antique shops, great restaurants including Brewster Fish House and Brewster Coffee House and The Brewster... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed August 19, 2015
    What a nice little home! Great newly remodeled kitchen, nicely sized rooms and a huge backyard, fully equipped with everything you need. We'd never stayed in Brewster before but...
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    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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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    Brewster, Cape Cod 02631
    1 / 21
    5 of 5 stars (5) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This immaculate Cape house was custom-built in 2000 and is conveniently located in desirable East Brewster close to Orleans center. The one-acre plot overlooks a tranquil cranberry bog and Vespers Pond via sun dappled woods, with a rustic country feel of the Cape. Enjoy modern amenities such as... View all property information
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    Brewster, Cape Cod 01863
    5 of 5 stars Reviewed July 23, 2015
    Our family needed a relaxing vacation and this charming home met our need. The house is very clean and extremely spacious. Every cabinet holds supplies such as paper goods...
    4 of 5 stars Reviewed July 20, 2014
    The location of the house is convenient to the entire Cape and the secluded location is overall very quiet. The kitchen was well stocked with utensils and supplies. Linens were...
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    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Secluded ranch set far back off the road in a wooded setting. This meticulous home offers one level living with 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... View all property information
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    Brewster, Cape Cod 02631
    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Wi-Fi
    • Central Heating
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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... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed 1 week ago
    A great place to stay!! Owner was very thoughtful and accommodating! Will definitely stay here again.
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    1 / 29
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    NOTE: Listed rates reflect a $400 reduction for open weeks! Sleeps 10 Near Crosby Landing Beach, Brewster 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... View all property information
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    Brewster, Cape Cod 02631
    1 / 14
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Nice and quiet, clean and updated, 3 bedroom, 2.5 bathroom house is close to wonderful restaurants, great shopping, Cape Cod National History Museum, Brewster General Store and best of all 5/10ths of a mile to Saint's Landing Beach! The master bedroom with queen bed and full bathroom are downstairs... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed August 13, 2014
    Stayed here for a week and could not have been more pleased. Location in perfect, house is amazing and owner very helpfull....will definitely been contacting them again next time...
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    1 / 24
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Sweet Cottage on Private Bayside Beach 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 space with Bay views you'll never... View all property information
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    Brewster, Cape Cod 02631
    1 / 41
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Upscale cottage, right on the beach! $8,500 PRIME SUMMER WEEKLY RATE If you're looking for the ultimate beachfront experience, consider Summerwinds, this one-of-a-kind upscale bungalow on the Bay in Brewster. From the renowned artists' work adorning the walls to the luxurious bed linens and terry... View all property information
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    Brewster, Cape Cod 02631
    1 / 25
    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... View all property information
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    Brewster, Cape Cod 02631
    1 / 37
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Terrace
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    Secluded home on the beach on Cape Cod Bay! $5,500 - $5,700 PRIME SUMMER WEEKLY RATE What a great location! Dune Road is an unpaved quiet road that runs parallel to the beach. The house sits on a private treed lot with fantastic views of the water. There is a small private path from the back yard... 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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    Patio faces golf course ninth tee,short walk to pools ,restaurants ,bike trail,borders Nickerson state park,bay a mile ,bring your own linen or rent, gas grill, parking in front of unit,decor has sea shell ocean theme,light and bright,friendly neighbors,(Ocean Edge is a pristine Resort of 500 acres... View all property information
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    Brewster, Cape Cod 02631
    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    WEEK OF JUNE 25- JULY 2 REDUCED 15%+ -- NOW ONLY $2,950! Directly on the Bay in Brewster with AC Peak Summer Weekly Rate: $4000 It's rare to find a Brewster family cottage with this much seclusion, directly on a private neighborhood beach! Perched atop the dunes and virtually invisible from... View all property information
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    Brewster, Cape Cod 02631
    1 / 33
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Custom Built New Home, 3 Minutes To Beach$5,200 PRIME SUMMER WEEKLY RATE Please Note: This property rents Sunday to Sunday during July and August. See tempting off-season rate reductions for June and September It's a custom built home in the Ellis Landing Beach section of East Brewster with a... View all property information
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    Brewster, Cape Cod 02631
    1 / 13
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    We rent our property by the week, Saturday to Saturday.<BR><BR>This bright, freshly remodeled home in a lovely, quiet setting features something for everyone in your vacationing group...<BR><BR>For the gourmet: a fun, light, stainless and Corian kitchen, fully equipped with new appliances, butcher... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed July 18, 2015
    My family and extended family total 10 people including my 2 year old nephew stayed here July 11-18th and we had a blast! This house is truly charming with its different decor and...
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    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Hot Tub
    • Shared Indoor Pool
    • DVD Player
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    Make our sunny and bright home your vacation retreat. This is a family friendly townhouse. You will appreciate the only 2 minutes walk to the Fletcher indoor/outdoor pool complex ( pool passes included*). Park your car right in front of the house and come in. Enjoy the warmth of this two story... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed August 27, 2015
    The vacation rental is clean, spacious and everything has been thoughtfully provided by the owners. We enjoyed the DVD collection, puzzles for the children and even found beach...
    5 of 5 stars Reviewed September 28, 2014
    This townhouse was a great place to stay as it was well appointed, bright and a good location. There was a nice selection of DVDs and games for all ages. It was easy to get to...
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    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    139 Nelson St., Brewster -(ID# 95702) ~ Private Association Beach 2/10 mile This great vacation home is 2/10 of a mile to a private association beach on Cape Cod Bay! This quintessential beach cottage has distant views of Cape Cod Bay from the front yard, a great screened in porch, a wonderful... View all property information
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    Brewster, Cape Cod 02631
    1 / 29
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Why pay the new Homeaway/VRBO surcharge? Book with confidence and save when you book direct with Pretty Picky. Spacious Home, Walk to Town, Linens Included! (Pets Considered) Peak Summer Weekly Rates: $3,600 - $4,000 Expansive home in the heart of Brewster, north of 6A! The home has 5 bedrooms, 3... View all property information
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    Brewster, Cape Cod 02631
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    NOTE: Rates Listed Have Been Reduced Up to $400 for Available Peak Summer Weeks! New Listing for 2016 One-Minute Walk to Private Beach, Cape Cod Bay View Peak Summer Weekly Rate: $3,800-$4,000 Elevated views of Cape Cod Bay and its sensational sunsets from the second level deck! This upside down... View all property information
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    Brewster, Cape Cod 02631
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    NOTE: Rate Listed for June 25 - July 2 Has Been Reduced $300! Waterfront Brewster Cottage with Private Beach A classic 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 including this one.... 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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    Nice & Roomy, 4-Minute Walk to Sandy Beach Peak Summer Weekly Rates: $4,000 - $4,200 (Sunday to Sunday Rental) There is living space on three levels in this house. There's a good sized living room on the main level, which flows into the open dining area and out to the screened porch. A deck wraps... 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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    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... View all property information
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    Brewster, Cape Cod
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    28 Cross St., Brewster -Property ID: 116479 This lovely home is just 1/10 mile to a private association beach on Cape Cod Bay. Spacious living areas on both 1st and 2nd floors with 5 bedrooms, 2 full baths, plus an enclosed outdoor shower. Close to Brewster restaurants and ice cream after soaking... View all property information
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    Brewster, Cape Cod 02631
    1 / 32
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    NOTE: Rate Listed for June 25 - July 2 Has Been Reduced $500! Togetherness & privacy in big Bayside home It is a house meant for family and friends to gather. There is space to be together as well as space to be apart. There is a living room as well as a family room off the kitchen. Both have... View all property information
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    Brewster, Cape Cod 02631
    1 / 54
    5 of 5 stars (16) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    The perfect vacation home with beautiful water view from the highest point on Sheep Pond!Vacation in winter is also possible."The winter view from our bedroom window shows the pond's unfrozen area, which marks the upwelling of the natural spring feeding Sheep Pond, giving it the cleanest water in... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed June 15, 2016
    Outstanding house! Big enough for our group of 7. Awesome view over Sheep Pond! In the 'middle' of the cape, so can get everywhere quite easily. Really nice...
    5 of 5 stars Reviewed September 24, 2015
    House was clean, comfortable and had great views. Neighborhood was quiet. If we travel to the Cape again we will definitely look to stay there.
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    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Enjoy vacation in a homey ambiance, located just a short drive from Brewster's Bay beaches, ponds, golfing and the Cape Cod Rail Trail. The kitchen has been updated with new appliances and tile work and a colorfully furnished and decorated screened porch leads out to beautifully maintained lawns... View all property information
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    Brewster, Cape Cod
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This two bedroom, two bath, pet-friendly home offers pond views from almost every room and is just a short walk away from the Cape Cod Rail Trail! This newly renovated property is situated on a private, wooded lot and offers an open layout, new hardwood floors and fresh paint. Both the living and... View all property information
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    Brewster, Cape Cod
    1 / 30
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Cheery Cape Beach Cottage Directly on Cape Cod Bay $3,800 PRIME SUMMER WEEKLY RATE $4,000 SUPER PRIME WEEKLY RATE -- JULY 23 - AUGUST 13 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... View all property information
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    Brewster, Cape Cod 02631
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This quintessential beach cottage has views of Cape Cod Bay from the front yard. Gorgeous vacation home just .1 mile to a private association beach on Cape Cod Bay! You will love the screened in porch, a wonderful outside shower, and a simply relaxing and charming atmosphere. Home has 4 large... View all property information
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    Brewster, Cape Cod 02631
    1 / 40
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Renovated beauty on the beach in Brewster $5,800 PRIME SUMMER WEEKLY RATE 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 provides warm calm water and of... View all property information
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    Brewster, Cape Cod 02631
    1 / 19
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    86 Leland Rd, Brewster MA (ID# 127516) This Cape Cod single story home is located in a quiet neighborhood in lovely Brewster near Upper Mill Pond for kayaking. A wonderful deck with Gas Grill, seating and folding awning overlooking private yard short distance to Paines Creek Beach on Cape Cod Bay.... View all property information
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    Brewster, Cape Cod 02631
    1 / 15
    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... View all property information
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    Brewster, Cape Cod 02631
    1 / 13
    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,... View all property information
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    Brewster, Cape Cod 02631
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Great opportunity to rent this 4 bedroom house starting at $1000 per week. This charming home is located less than a mile from Breakwater Beach and a short distance from the Brewster General Store. The first floor offers a kitchen with a separate dining room, ample living room with a flat screen... View all property information
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    Brewster, Cape Cod 02631
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Bay Views, 2 Minute Walk to Beach, Sleeps 10 Adjusted Rates Shown for Open Weeks Reflect Reductions Up to $500! This home is very close to its private neighborhood beach, just to the west of Brewster's public Breakwater Beach. The beach is a two-minute walk along the quiet neighborhood road that... 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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    This charming, immaculately kept Cape is about 2 miles to Captain’s Golf Course, just over a mile to swimming, boating and fishing on Pleasant Bay, and a short drive to Harwich or Orleans shopping centers, theaters, etc. The kids will enjoy the yard by day and the lower level play area/den by... View all property information
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    Brewster, Cape Cod
    1 / 35
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    NOTE: LISTED RATES FOR OPEN WEEKS REFLECT REDUCTIONS UP TO $600! Striking Bay & Crosby Landing Beach Vista 168-B (Pets Considered) 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 a long driveway with plenty of... View all property information
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    Brewster, Cape Cod 02631
    5 of 5 stars Reviewed May 15, 2016
    A wonderful vacation property set on the edge of the flats with panoramic views of Cape Cod Bay. It had everything our family needed to enjoy a restful break, a hidden gem!
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Three Minutes to Beautiful Private Brewster Beach, Big, Roomy, 4 BR, 4.5 Baths OFF-SEASON WEEKS AVAILABLE FROM $1,900! Off-season minimum 3 nights. This house really has something for everyone. We think it is one of the more comfortable and fun houses for a group since there are so many places to... View all property information
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    Brewster, Cape Cod 02631
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Upscale home, 200 feet from private beach near Ellis Landing (Linens included) Peak Summer Weekly Rates: $4,500 - $5,200 (Pets Considered) 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 Landing neighborhood in... View all property information
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    Brewster, Cape Cod 02631
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Attractive, well maintained, comfortable Cape in a quiet neighborhood convenient to Captain's Golf Course, Long Pond, Sheep Pond, Nickerson State Park and the Cape Cod Rail Trail Trail. It has a lovely sunroom, patio, and private backyard - perfect for relaxing after a day at the beach, on the... View all property information
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    Brewster, Cape Cod
    1 / 17
    4 of 5 stars (1) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    This large 4 bedroom house is located on a one acre wooded lot adjacent to Nickerson State Park and close to all the amenities of beautiful Cape Cod. The house has an open space floor plan on the first floor, all hardwood floors and tiled baths. There is a large deck with wrap around benches and a... View all property information
    Location Information
    Brewster, Cape Cod 02631