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Holiday Rentals in Brewster

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    ₹ 19,880 Average
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    Travellers to Brewster are booking July dates now. Secure your holiday home today, and have the perfect trip.
    All 179 Rentals in Brewster
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Rustic yet charming, this lakefront cottage provides privacy and spectacular waterviews from every room. Pets are welcome! Multiple sliding doors open to a private wrap around deck with lounge chairs, dining table, gas outdoor grill and an outdoor shower; all for your entertaining pleasure....
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    RATE REDUCED $1,000 FOR LAST OPEN PRIME SUMMER WEEK -- JULY 9-16! Breathtaking Views Directly On Sandy Beach Please note:  This property 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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Beachfront Brewster with Elevated, Sweeping Bay Views 116-BK $5,100 - $5,300 PRIME SUMMER WEEKLY RATE (Rents Saturday to Saturday during peak season) This two-story beach house is directly on the beach and Cape Cod Bay, with outstanding 180-degree views of the water. For many, when they picture a...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Renovated beauty on the beach in Brewster $5,900 PRIME SUMMER WEEKLY RATE (Rents Saturday to Saturday during peak season) 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....
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    NEW LISTING for 2017 Two Cottages with a Brand New Pool, ½ mile to Private Beach More pictures coming soon! $4,250-$4,500 PRIME SUMMER WEEKLY RATE - Linens Included (Rents from Saturday to Saturday) Be one of the first guests to stay at this two cottage compound that features a brand new in-ground...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Architect Owned & Renovated, Bay Views, One Minute to Beach $7,500 - $7,800 PRIME SUMMER WEEKLY RATE Please note:  This property rents Sunday to Sunday. This is an architect's vacation home tucked away in a very quiet neighborhood in Brewster with Bay views and a two-minute walk to an ideal sandy...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    28 Cross St., Brewster -Property ID: 116479 2017 Season! 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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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 & 4 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, 2 Bathrooms, Sleeps 8 Quick View
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    Renovated, Light & Bright Brewster Beachfront Property PEAK SUMMER WEEKLY RATES: $5,800-$6,000 (Rents Saturday to Saturday during peak season) It's 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    RATES REDUCED $1,000+ FOR REMAINING OPEN PEAK SUMMER WEEKS ONLY! Rates shown reflect adjustments. (Rents Sunday to Sunday during peak season) Seven-night stays only, no weekends or partial weeks. Loads of Living Space at New Brewster Home by the Beach The beautiful house was built in 2007 and...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Great 3 bedroom home located on a cul -de -sac with a very short walk to Linnell Landing Beach and beautiful sunsets. Large screened porch and a covered patio to enjoy those summer evenings. A gas grill is also available. Nearby is Nickerson State Park, bike paths, live theater and Many fine...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Rates Shown Have Been Reduced $300/week for Remaining Open Weeks! 4-Minute Walk to Sandy Beach, Loads of Living Space, In & Out (Rents Sunday - Sunday during peak season) 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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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 (Rents Saturday to Saturday during peak season) 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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. (Rents Saturday to Saturday during peak season) Enjoy a bayside beach vacation in a timeless cottage tucked into the dunes near Ellis...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Spacious, Updated Value, 2 Minutes to Beach Week of July 22 now $2,995! (Rents Saturday to Saturday during peak season) Lock in off-season weekly rates from $1,500. Ask about off-season three-day-weekend and partial week rates. Here's one of the best private home vacation values you'll find in...
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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. $4,800 - $5,000/week in Peak Summer. (Rents Saturday to Saturday during peak season) 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Ranch style home on golf course with loft. Sleeps 8. There are 4 twins, full size sofa sleeper and a king bed. First floor is all tile with area rugs baking it more sanitary than carpeting. Wall mounted air conditioning units in bedrooms and vaulted ceiling living area.
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    RATE REDUCED $900 FOR ONE REMAINING OPEN PEAK SUMMER WEEK ONLY! Rate shown reflects rate adjustment:  $3,900/week June weeks reduced still more! (Rents Saturday to Saturday during peak season) Water views, 150 feet to private beach. It's a two-story vacation home with wonderful views of Cape Cod...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Come stay at: Jack's Little Cape House! Updated Brewster MA Vacation Rentals with Central Air and Wifi. Peak Summer Weekly Rates:  last week of June until the first week in September: $1,600/week. All amenities at our Brewster MA Vacation Rentals including Central AC and flat screens in each room....
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    This newly listed, beautiful 4 bedroom, 4 bath home features breathtaking panoramic views of Paine's Creek and Cape Cod Bay. It's spacious layout offers sleeping for up to 12, so bring the whole family! The first level of the home offers a roomy living area with sliders to the patio, sunroom with...
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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 10 Quick View
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    Custom Built New Home,  3 Minutes To Beach $5,200 - $5,400 PRIME SUMMER WEEKLY RATE (Rents Sunday to Sunday during peak season) 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...
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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 8 Quick View
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    • Washer
    • Balcony
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    Pristine Brewster pond front vacation rental home right on Blueberry Pond. Gorgeous views from almost every room in the house. A/C, WIFI, deck with water views, gorgeous kitchen and plenty of space make this a perfect vacation rental home for the whole family to enjoy. Paddle board or kayak with...
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    Brewster, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Upscale cottage, right on the beach! $8,250 - $8,650 PRIME SUMMER WEEKLY RATE (Rents Saturday to Saturday during peak season) 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 2 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 PRIME SUMMER WEEKLY RATE:  $7,600 - $8,000 (Rents Saturday to Saturday during peak season) 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Price Range $2195-$4320 This 3 bedroom, two bath townhouse is impeccably appointed and the first floor features a living room with LGHD TV, am/fm stereo, and CD player. There is a full bathroom with walk in shower accessible from both the hallway and bedroom, a large kitchen fully stocked with...
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    Brewster, Cape Cod 2631
    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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    Brand New Custom Brewster Home with Pool, 4 Min Walk to Private Beach More pictures coming soon! $4,950-$5,500 PRIME SUMMER WEEKLY RATE - Linens Included (Rents from Saturday to Saturday) Be one of the first guests in this brand new home for summer 2017.  The house is located on a HUGE lot with a...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Sweet Cottage on Private Bayside Beach $3,800 WEEKLY PRIME SUMMER RATE 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Price Range $1925-$2375 The moment you cross the threshold of this standalone Ocean Edge home, your perspective will downshift into vacation gear. All furnishings are exquisite; all seating - from sofa to chairs - are beyond comfortable. Gleaming hardwood floors shine throughout the first floor,...
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    Brewster, Cape Cod 2631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Classic Brewster Cottage Steps from Private Beach, Water Views, Pets Considered. Prime Summer Weekly Rate:  $2,900-$3,200/week (Rents Saturday to Saturday during peak season) A classic Brewster cottage perched overlooking Cape Cod Bay, this property is an ideal beach retreat.  The large open yard...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Charming vacation home in a quiet neighborhood with pedestrian and biking access to abutting Nickerson State Park. Great location for hiking, biking, kayaking, swimming and fishing! Explore the nature trails to nearby Cliff Pond which is less than 1/2 mile away. This 3 bedroom ranch has a finished...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Newly Updated Brewster Cottage, 150 feet from Private Beach PRIME SUMMER WEEKLY RATE:  $1,900 - $2,400/week for remaining open weeks! (Rents Saturday to Saturday during peak season) The new owners of this adorable cottage have completed many upgrades to give the cottage the classic Cape feel with...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Just 1500 ft. to Private Beach!! This gorgeous 4 bedroom, 2 bath Brewster vacation rental home is located just 2/10th of a mile to a fantastic neighborhood beach on Cape Cod Bay. This lovely home is done in and out. The amenities include washer / dryer, A/C, internet, cable TV, DVD, deck, deck...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    #801 Hillcrest House: Family Retreat! 300 Ft. from clear spring fed water at Sheep pond Private association beach. A hop and skip to crystal clear Sheep Pond, spring fed and one of Cape Cods cleanest. Water views and 1-minute walk down the hill to private association beach for swimming, kayaking...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hello & Welcome to my Two Bedroom - Two Bath Townhouse which is an End Corner Duplex and is located in Brewster on the Premier Ocean Edge Resort & Golf Club Property~Sponsored Guest Passes are Available for Swimming Pools - Tennis Courts - Bike Rentals - State of the Art Fitness Gyms and NEW!...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Price Range $1575-$2095 Come to Ocean Edge Resort in Brewster and vacation on Cape Cod in this A Style two bedroom, two bathroom condo with a loft that has access to Ocean Edge Resorts Indoor & Outdoor Pools. This sunny condo features new wood floors in the living & dining room and also has been...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 BEDROOM/ 2 BATH OCEAN EDGE GETAWAY!1 / 32
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Price Range $1370-$2070 Affordable Brewster Getaway! Fletcher Indoor Pool is Open Year Round! Brewster's Desirable Ocean Edge Resort, this "B" Style townhome located in Fletcher Village just a short distance from the Fletcher indoor/outdoor pool, fitness center, tennis courts, has A/C, and much...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    86 Leland Rd, Brewster MA (ID# 127516) 2017 Season! This Cape Cod single story vacation home is located in a quiet neighborhood in lovely Brewster near Upper Mill Pond for kayaking, paddle boarding etc. Close by is the General Store, Shops and Restaurants. Wonderful deck with Gas Grill, seating...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Charismatic Cape Cod house, built in the 20s by the groundskeeper for a nearby estate, shows post and beam construction, rambling New England Extended Architecture accented with all new, sustainable renovation right down to the appliances. Gather your family and friends in this beautiful Brewster...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    We love the cape. Nothing like a warm and balmy day or night on the beach. Our home is in a safe and self-contained environment for family with small children. There are many activities, including swimming, golf, tennis, basketball, biking, hiking, summer camp activities for children. Our guests...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Price Range $1675-$2215 Just listed! Recently renovated with new bedding and furnishings, this 3 bedroom/3 full bath Brewster home sits at the end a super private acre lot only 0.3 miles from a peaceful bay beach. You enter the house from an ample side deck with outdoor dining furniture for 8, a...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Patio home free standing .House has been done over with a new kitchen ,baths,rugs , tiles,windows,Central air.Has a nice open concept with a spiral stair case to an upper bedroom.First floor bedrooms have mounted flat screen tv's with a flat screen in the main room.Enlarged patio with gas grille...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Magical Waterfront Vacation Home on Freshwater Pond. Announcing a kitchen make over for 2014, includes a new floor, counter tops and fresh coat of paint. Three bedroom, 1 and a half bath house offers a tranquil setting for a summer vacation close to beaches, shopping, restaurants, golfing and...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Middlecott Village Patio Home with loft - sleeps 6. Central Air and WiFi! This property currently includes pool privileges which are available at an additional fee.* Spend hours on the over-sized patio and enjoy the excitement of golf right in front of you, or the tranquility of the pond to your...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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