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Brewster Holiday Homes

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    Travellers to Brewster are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 258 Rentals in Brewster
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Open, spacious and airy: All words that best describe this rental in charming Brewster. Located just .5 miles to Crosby Landing Beach, this home is perfectly situated to offer you all the best that the Cape has to offer. Spend the day at the beach, and then explore the Old King's Highway (Route 6A)...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    116 King Philip Road Bfrewster MA (ID# 116159) 2018 Season! Sparkling 3 bedroom home near the bike trail, bay beaches and Nickerson State Park. The house features central A/C with a bright sunroom overlooking the back yard, deck and outdoor shower. The living room has a gas fireplace and flat...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Bayside, King Bed, Central AC, Beach #2, Association Tennis & Outdoor Pool #9 Located on Spicebush Terrace, this desirable Bayside townhome features an updated kitchen, central AC and wood floors on the main floor. The master bedroom is upstairs and offers a king bed, TV with DVD player, a...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    A-Style, 2 ACs & 6 Pool Passes (Fees Apply) Ready to Rent for the 2018 Season. This spacious Billington Village unit features an updated kitchen, and 2 bedrooms plus a loft sleeping area. Up the spiral staircase is the master bedroom with a queen bed, flatscreen TV, AC, and private bath. The...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Edge Townhouse (sleeps 6) with King Bed  & Straight Staircase - BI05481 / 16
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    B-Style, King Bed, Straight Staircase, 2 A/C & 6 Pool Passes (Fees Apply) This tastefully decorated townhouse located at the entrance of Billington Village is a short walk to Arbor pool and features newer carpeting and paint. The master bedroom is located on the first floor and offers a king...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    C-Style, 55' HDTV, Straight Staircase, 3 ACs, WIFI & 6 Pool Passes (fees apply) This very lovely Billington Village townhouse features newly installed ductless AC and a 55' HDTV. The first floor features an air-conditioned living room with a large sofa bed, comfortable accent chairs, a half...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    B-Style, Renovated, King Bed, Straight Staircase, Enclosed Loft, 2 ACs, 6 Pool Passes (Fees Apply) This beautiful, Howland Village townhouse features many updates that include a straight staircase, wood floors, newer carpet, updated kitchen and baths, and newer furniture. Both bedrooms have...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Edge - Upper Level End Unit - EA01411 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Upper Level, End Unit, Updated Kitchen, 1 AC Ready to Rent for the 2018 Season This tastefully decorated, Eaton Village apartment features sunny rooms and private wooded views. The master bedroom has a queen bed, TV with VCR, and private bath. The 2nd bedroom has 2 twins and TV with DVD. Both...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sleeps eight, directly on the beach -- now with air conditioning! Peak Summer Weekly Rates:  $5,500 - $5,900 Rents Saturday to Saturday Linens not included 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Welcome to The Nautical Star! Adorable totally updated cottage with everything new and Slimline Very short walk of 0.3 miles to Paines Creek Beach. Adorable totally updated cottage with everything new and Slimline AC in the bedroom! Very short walk of 0.3 miles to Paines Creek Beach. Enjoy this...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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 Rental with Central Air and Wifi. This home offers Central AC and flat screens in each room. It is located in a residential neighborhood with easy access to the bike trail, bay side, and shopping.  It has hardwood floors through...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Street Level, Solid Flooring, Linens Included, 2 ACs, 6 Pool Passes (fees apply) This Chilton Village apartment features a lovely golf course view and solid flooring throughout. The master bedroom has AC and offers a queen bed, flatscreen TV, ceiling fan, and a private bath. The 2nd bedroom...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Short walk to Upper Mill Pond, 2.3 miles to beautiful Paines Creek Beach on the Bayside Located in a private setting this 3 bedroom 2 bath single level home is just a half mile from a shared private association beach at Upper Mill Pond. The master bedroom has a queen size bed with private bath....
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    B-Style, Renovated, Straight Staircase to Semi-Enclosed Loft, 3 ACs, 6 Pool Passes (Fees Apply) This tastefully renovated townhouse is located in a private area at the end of Billington Village. It features hardwood floors, a beautifully renovated kitchen and dining area, and a living room with a...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Edge Townhouse with A/C & Pool (fees apply) - HO00301 / 18
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A-Style, Renovated, Straight Staircase, 2 ACs, 6 Pool passes (Fees Apply) This spacious, renovated Howland Village townhouse is beautifully decorated and features a straight staircase and Pergo flooring throughout the main floor. You'll find the master bedroom upstairs with a queen bed,...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Paines Creek Beach!! The beautiful and comfortable Cape Cod vacation rental has 3 bedrooms & 2 full bathrooms. At this lovely Brewster rental home you can enjoy a spacious yard with a beautiful deck area. It is located just 1 mile to gorgeous Paines Creek beach on Cape Cod bay and 1 mile to...
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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 8 Quick View
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    • Waterfront
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    B-Style, Solid flooring, 3 ACs & 6 pool passes (fees apply) Located in a quiet part of Billington Village, this lovely townhouse features AC in both bedrooms plus the living room. In 2016, solid flooring was installed throughout the main floor. The master bedroom is on the main floor and...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 Linens not included 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Patio Style, Golf Course Views, 3 ACs, WIFI & 6 Pool Passes (Fees Apply) This Susanna Village patio home is located on the 15th green and offers ductless AC units in both bedrooms. The master bedroom has a queen bed, AC, ceiling fan, flat screen TV, and private bath. The 2nd bedroom has 2...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Private Dock on Lower Mill Pond, Waterviews Built in 2004, this recently painted home faces southwest on Lower Mill Pond for magnificent sunsets in a beautiful, secluded setting. Take a morning dip in the pond from your own private dock just 50 feet from the house. (Use our Virtual Tour to take a...
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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 7 Quick View
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    Upscale home, 200 feet from private beach near Ellis Landing (Linens included) Peak Summer Weekly Rates: $4,100 - $5,200 (Pets Considered) Rents Saturday to Saturday during peak season This is a newer beach house built in 2005. It is a 3 bedroom, 2 ½ bath home about 200' from a private association...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    $1125-$1625 Rates include all agency charges. Ocean Edge bills separately to use the resort amenities. This street level garden villa for 6 guests has a definite beachy feel, and is located within walking distance to Fletcher or Arbor pool complexes as well as the tennis courts and the Linx Tavern....
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 Linens not included 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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    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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    Ocean Edge: St.  Level 2 BR, 2 Bath (sleeps 5), 2 A/C's w/pool (fees apply) - EA01151 / 14
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Street Level, Renovated Kitchen, 2 ACs, 5 Pool Passes (Fees Apply) Ready to Rent for the 2018 Season This Eaton Village apartment features a renovated kitchen and a nice wooded view from the patio. The air-conditioned master bedroom has a newer Simmons Beautyrest queen bed, a ceiling fan,...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    C-Style, Straight Staircase & 4 Pool Passes (fees apply) This Billington Village townhouse is a short walk to Arbor Pool and the Linx Tavern. The 2 bedrooms are upstairs, along with the full bath. The master bedroom has a queen bed, and a ceiling fan. The 2nd bedroom has 2 twin beds, and a...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    C-Style, Renovated, Straight Staircase, Close to Fletcher Pools, 2 Ductless ACs, WIFI & 4 Pool Passes (Fees Apply) Located close to the Fletcher pools, tennis & basketball courts, this desirable Trevor Village townhouse features renovated bathrooms and kitchen, plus new furniture in the living...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Upper Level, Murphy Bed, 2 ACs & 4 Pool Passes (Fees Apply) Ready to Rent for 2018 Season! This bright, updated, Fletcher Village apartment overlooks the golf course from the deck. The air-conditioned bedroom has a queen bed and ceiling fan. The fully equipped kitchen has all the amenities of...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lovely setting at this serene location in Brewster. This well kept home has 3 bedroom, 2 bathrooms and an outdoor eclosed shower. Here you will enjoy a quiet and private location near Nickerson State Park, easy access to the Bike Trail and convenient drive to the best beaches. There is A/C units...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A-Style, Pond & Golf Course Views, 2 ACs This spacious Billington Village townhouse has lovely pond and golf course views that can be seen from the living room and patio. The first level offers a full bathroom, a fully equipped kitchen and dining area, a living room with AC and large, flat screen...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Close to Fletcher Pools, 2 AC's, 6 Pool Passes (fees apply) This sunny B-style townhouse is located at the entrance to Howland Village. The first floor master bedroom has a queen bed, ceiling fan, and flat screen TV. Up the spiral staircase, you will find the 2nd bedroom (open loft) which...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Basement Level, Murphy Bed, 3DTV, 1 AC, 4 Pool Passes (Fees Apply) This basement level (down 12 stairs from the street entrance), Fletcher Village apartment is located across from the Fletcher pools and tennis courts and features a 3D TV and a newer, memory foam mattress in the bedroom. The...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Beachfront Brewster with Elevated, Sweeping Bay Views Peak Summer Weekly Rates: $5,100 - $5,300 Rents Saturday to Saturday Linens not included 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 cottage...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Property ID: 22713 / Key #: 4073 / Property Name: 81 White Oak Trail 2017 Summer Rental! This charming ranch style home is located in a quiet residential neighborhood. Three bedrooms with a full bath, comfortable living room, quiet back deck off dining area to sit and relax. Close to bay beaches...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A-Style, Fully Renovated, 2 King Beds, Straight Staircase to Enclosed Loft, 4 ACs, WIFI & 6 Pool Passes (Fees Apply) Ready to Rent for 2018 Season Wow! This A-Style townhome in Howland Village has just been completely renovated and has all the features that vacationers are looking for: king...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Edge Lovely Patio Style with A/C & Pool (fees apply) - SU00531 / 18
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Patio Style with Full 2nd Floor w/half bath, Golf Course Views, 4 ACs, WIFI & 6 Pool Passes (Fees Apply) Located in Susanna Village with lovely views of the golf course, this unique patio home offers a full second floor with a private bedroom plus a den with a bonus half bath. The owners have...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Street Level, 1 AC, Updated, 4 Pool Passes (Fees Apply) This lovely Eaton Village apartment is located in a quiet area and features peeks of the golf course, solid flooring throughout the entire unit, and an updated kitchen. The master bedroom has a queen bed, TV and private bath. The 2nd...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Breathtaking Views Directly On Sandy Beach Peak Summer Weekly Rates:  $4,900- $5,500 Rents Sunday to Sunday Does not include linens 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 situated to take best advantage of...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    $1925-$2375 Rates include all agency charges. Ocean Edge bills separately to use the resort amenities. 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...
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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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    125 Bog Pond Road (ID #133097) ~ Bayside four Bedroom Home ~ Brewster 2017 Season! This is a spacious open and bright home set in a private location in Brewster. This newly renovated 4 BR/2 BA home has hardwood flooring on the main level, updated furnishings & has been freshly painted. There is an...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    $1575-$2070 Rates include all agency charges. Ocean Edge bills separately to use the resort amenities. 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...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Spacious, Updated, Great Value. Walk Two Minutes to Beach. Peak Summer Weekly Rates:  $3,500 Rents Saturday to Saturday Linens not included 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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Shared Indoor Pool
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    • Housekeeping Included
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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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    Sleeps 10 Near Crosby Landing Beach -- 050-B1 / 30
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Sleeps 8, Walk to Crosby Landing Beach, Brewster. Totally renovated kitchen for 2017. Peak Summer Weekly Rates:  $3,800 - $4,500 Rents Saturday to Saturday Linens not included An 8-10 minute walk from this big and neat-as-a-pin two-story home brings you to sweeping Crosby Landing Beach, considered...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Brewster Home with Pond rights, includes Bikes, Kayaks...Updated Home!1 / 28
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    June Special Rate $1,100 week! At the end of a cul de sac this home is nestled between Canoe Pond and Upper Mill Pond with a deeded beach just steps away! This Comfortable 2 level home has all the comforts that you require. The Open Floor plan boasts a fire placed Living room (Queen size fold out...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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