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Brewster Luxury Holiday Rentals

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    Travellers to Brewster are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in BrewsterView all 177 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    On the Dunes Overlooking Cape Cod Bay1 / 17
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Rights to Brewster's Best Private Beach1 / 14
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    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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    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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Custom Beach House Directly on the Water RATES SHOWN REFLECT REDUCTION UP TO $900/WEEK! For remaining open weeks only Prime Summer Weekly Rates:  $5,500-$6,500 Rents Saturday to Saturday Owners have replaced the original cottage on this property with a totally new, two-story vacation home.  From...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Big and Beautiful on the Beach in Brewster -- Sleeps 14+ Peak Summer Weekly Rates: $13,500 - $15,000 Rents Saturday to Saturday during peak season Linens included Please click on the 'Virtual Tour' to see a 3D tour of the home This truly is a special property, the ideal vacation headquarters...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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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:  $6,950 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: central AC,...
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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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    New Construction Right on the Beach, Sleeps 8, Linens Included Peak Summer Weekly Rates:  $7,200 - $7,600 Rents Saturday to Saturday RATES SHOWN REFLECT REDUCTION UP TO $600/WEEK! (For remaining open weeks only) Owners have replaced the original cottage on this property with a totally new,...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    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 a quick 4-5 minute...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 5 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: $7,100 - $7,500 This is the perfect vacation headquarters for your multi-generational or multi-family group. You are privately and ideally situated directly on Brewster's...
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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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    Beachfront, Renovated, Light & Bright  Peak Summer Weekly Rates: $6,000- $6,300 Rents Saturday to Saturday Linens Included   A welcoming 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...
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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 10 Quick View
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    Upscale Cottage Experience, Right on the Beach Peak Summer Rates: $8,750 - $9,200/week Rents Saturday to Saturday Includes Linens, Bedmaking   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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 2 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:  $6200 Rents Saturday to Saturday Linens Included The property is as close to the water as you can get! Four steps from the main level deck brings you to the private stairs down to the private beach only shared by two 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 6 Quick View
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    108 King Fisher Cartway Brewster MA (ID# 18141) ~Waterfront on Cape Cod Bay! 2019 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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Bayside Oceanfront - 3 BR, 3 Bath (Sleeps 6), Central A/C, Private Association Pool, Beach & Tennis BRAND NEW LISTING!! OCEANFRONT BAYSIDE Condo with Central A/C, located on the waterfront of Ocean Edge Drive. Imagine waking up and looking out to see the ocean right outside your door....
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 3 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: $5,750 - $6,800 (plus tax) Rents Saturday to Saturday during peak season Last open week (8/24) just reduced 10% This beautiful custom home is located near Paines Creek Beach, in fact there is...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Street Level, Golf Access, Updated, 3 BR 3 Full Baths, 3 ACs, WIFI, Phone Land Line & 8 Pool Passes (Fees Apply) - Featuring GOLF ACCESS and mostly RENOVATED! This spacious 1600 sq ft, Endicott Village condo has been renovated, updated, refreshed and is well decorated. The condo can accommodate...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Custom Renovation, Bay Views, 1-Minute Walk to Brewster Beach & Flats Linens and Bed Making Included Rents Saturday to Saturday During Peak Season This is what your extended family or two-family group has in mind for your Cape Cod summer vacation. With a complete renovation just completed and...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Impeccable Vacation Home, 200 Feet from Beach. RATES SHOWN REFLECT REDUCTION OF $500 FOR JULY 27 - AUGUST 3 WEEK ONLY! Peak Summer Weekly Rate: $4,900 Rents Saturday to Saturday Linens not included This is an immaculate and beautifully decorated 3 bedroom, 2 ½ bath home about 200' from a private...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 PRICE REDUCTION! $800 OFF! Prices already reflect. Here is a spectacular, renovated and tastefully decorated, contemporary, 4+ bedroom, 4 bath home sleeping 12 featuring panoramic views of Brewster's Paines Creek Beach...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    On the Beach in Brewster Large, Recently Renovated Home, Sleeps 10 $7,100 PRIME SUMMER WEEKLY RATE  Saturday to Saturday rental only Linens not included 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Modern, Magnificent & Private with Heated Pool Sleeps 16, Seven Bedrooms, Five Baths Linens, Bed Making Included, Pets Considered Rents Sunday to Sunday in Peak Summer Remaining Peak Weeks Reduced 15% Please click on the 'Virtual Tour'tab to take a 3D tour of the home Larger vacation groups...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Custom Built New Home, Three Minutes To Beach RATES REDUCED $400 FOR AVAILABLE PEAK SUMMER WEEKS! Rates shown reflect rate reductions for remaining open peak weeks only. Prime Summer Weekly Rates: $4,800 - $5,400 Rents Sunday to Sunday   It's a custom built home in the Ellis Landing Beach section...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Spacious Family Waterfront Home on 260 Acre Lake, Sleeps 14 Linens and towels included for stays of 7 days or more. Rents Sunday to Sunday during July and August MAJOR REDUCTIONS FOR OPEN JULY WEEKS, REDUCED $2500 FOR WEEK OF JULY 21-28.  Perfect for a large group!  This fantastic large...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    10 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    Magnificent Mansion, Privacy, Pool, Water Views in Brewster New Construction, New Listing as of July 29, 2019! Sleeps 22 in 10 Bedrooms, 9.5 Baths Linens and Bed Making Included Rents Friday to Friday in Peak Season   Just completed in 2019, here is the perfect luxury retreat for your discerning...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 22
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