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Holiday Rentals with Pools in East Dennis

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    29 Matching Rentals in the East Dennis AreaView all 169 rentals
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    The following rentals are within 10 kilometres of East Dennis.
    Townhouse in Brewster, Ocean Edge Resort1 / 14
    (11)Excellent
    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    DETACHED HOME IN THE PERFECT LOCATION AT OCEAN EDGE RESORT!1 / 23
    (1)Excellent
    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Brewster, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Saltwater Pool, 0.3 Miles to Beach, Central AC (Linens Included) $4,250-$5,200 PRIME SUMMER WEEKLY RATE The property rents Saturday – Saturday during July and August This gorgeous 3-bedroom, 2.5-bath house in Brewster is just steps to the beach and has central AC, a spacious back yard,...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Brewster, MA
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Big, Beautiful New Pool for 2019! Walk 3 Minutes to Beach Linens Included, Beach Towels Provided Pets Considered Peak Summer Weekly Rates: $4,900 - $5,200 Rents Saturday - Saturday during peak season Come splash in and relax by the exquisite new 18' x 36' in-ground, heated pool with 8' max...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Brewster, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the loveliest patio homes in Middlecott Village at Ocean Edge Resort, this stand alone house features 3 bedrooms, 2 full baths, Central A/C, an interior living space that is beautifully designed and comfortable, and an oversized patio with outdoor table, umbrella, and chairs for dining or...
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    Brewster, Cape Cod 2631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Two Bedroom Cape Cod Townhouse at Ocean Edge Resort ~ Perfect Get Away1 / 39
    (1)Excellent
    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Shared Indoor Pool
    • Cable/satellite TV
    • DVD Player
    • Sauna
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 January 2018
    Beautifuly furnised and very comfortable.Close to CC bay. Swimming pool and hot tub a plus!A golfers paradise when in season.
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    About this property
    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~Daily and Weekly Sponsored Guest Passes are Available for Swimming Pools - Tennis Courts - Bike Rentals - State of the Art Fitness...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Brewster, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded Brewster Home with Private Pool, Pets Considered, Linens Included Peak Summer Weekly Rate: $4,800 - $5,000 Rents Saturday to Saturday If you're looking for a modern home with plenty of privacy and your own private in-ground pool, look no further! The home is set on 1.8 private acres on a...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely Brewster Ocean Edge Resort patio home couldn't be in a better location! Situated in Middlecott Village directly on the fairway with views of Sol's Pond, you can truly unwind on the patio after a day of fun in the sun. This detached loft home features two bedrooms - one with a queen size...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster, MA
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Listing for 2018! Brand New Custom Brewster Home with Heated Pool, 4 Min Walk to Private Beach Sleeps 10, Linens Included Rents Saturday to Saturday Be among the first guests in this brand new home!  The house is located on a HUGE lot with a private in ground pool. In addition, the house is...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Brewster, MA
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern, Magnificent & Private with Heated Pool Peak Summer Weekly Rates:  $9,500 - $9,900 Sleeps 16, Seven Bedrooms, Five Baths Linens, Bed Making Included, Pets Considered Rents Sunday to Sunday in Peak Summer NEW Listing for 2018! Just Listed! Larger vacation groups will savor this nearly...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Patio
    • Parking
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This saltbox style home abounds with sunny colors and English Country ambience. The first floor features a super comfortable living room with TV & DVD player, fully equipped eat in kitchen with A/C and ceiling fan, a full bathroom with tub/shower combination, laundry, and a queen size bedroom with...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Brewster, MA
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 minute walk to one of Brewster's best beaches! Stunning brand new 5 bedroom, 4.5 bath custom home with in-ground Salt Water Swimming Pool close to Point of Rocks Beach in Brewster. Air conditioning throughout. Large open first floor living. Gourmet kitchen has breakfast bar with 6 stools. Dining...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “We have been coming to Ocean Edge for many years and this is our third time staying in this home. It is very homey and Mary Beth C., guest Enjoy Cape Cod at Ocean Edge Resort in Brewster in this nautically decorated two level town home located in the Village of Billington with 3 ductless A/C...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEST PRICE AT OCEAN EDGE RESORT!1 / 20
    (1)Excellent
    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2018
    Love Ocean Edge! Very clean, well manicured and family friendly resort. Condo is in Great Location between 2 major pool complexes. Fletcher Pools include an indoor pool for...
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    About this property
    This street level garden villa for 6 guests has a definite beachy feel, and is located in Eaton Village is within walking distance to Fletcher or Arbor pool complexes as well as the tennis courts and the Linx Tavern. The nautical décor in the air-conditioned living and dining area is an inviting...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New appliances and updated furnishings! The moment you cross the threshold of this standalone Ocean Edge home located in the Village of Middlecott, your perspective will downshift into vacation gear. All furnishings are exquisite; all seating - from sofa to chairs - are beyond comfortable. Gleaming...
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    Brewster, Cape Cod 2631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Housekeeping Included
    • Shared Indoor Pool
    • Sauna
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated, large, 1,200 square foot, 2 bedroom, 2 bath condominium. with living room and dining area. Unit has cathedral ceilings with bright open design. Unit also includes full modern kitchen, laundry and patio area with grill. Resort is centrally located in beautiful Brewster near...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recent first-floor renovation! Beautiful vacation home located in Trevor Village at the Ocean Edge Resort in Brewster, located in Trevor Village this is a two story town-home located just a couple minutes from the Fletcher indoor & outdoor pools. On the first level of this home, you will find brand...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Brewster, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Indoor Pool
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The family-friendly Villages side puts you footsteps from Cape Cod's only 18-hole Nicklaus Design golf course, pools and tennis courts, kayaking on Blueberry Pond, and the romantic 26-mile Rail Trail. The Beach House Spa, with expert wellness and beauty services, sits conveniently between both...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Brewster, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two Cottages with a Brand New Pool, ½ mile to Private Beach, Linens Included Rents from Saturday to Saturday Come enjoy this two cottage compound that features a brand new in-ground pool! These houses are also just a ½ mile to a private beach on Cape Cod Bay. This sandy stretch of beach is one of...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Grill
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look at the bay from the upper floor deck in this Sea Pines town home. Community has a private beach,tennis courts and outdoor pool. Close to golf courses (3 within 10 miles) and ocean Property wifi ready and in an ideal location 200 paces to the water!
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Ocean Edge Resort—2BR Condo on Golf Course w/ Pools1 / 24
    (1)Average
    Brewster, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    This is a nice condo with a lot of potential, It needs maintenance attention. Sliding glass door does not work. Bath mats need to be replaced. Chair is broken in dining room...
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    About this property
    You can have it all at Ocean Edge Resort & Golf Club. Step out from your 2BR/1.5BA condo and onto the beautiful fairway -- the course was designed by Jack Nicklaus and makes for an incredible backdrop for an afternoon game or a bike ride. Ocean Edge amenities are many: three outdoor pools, an...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Dennis, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PRIVATE POOL AND WATER VIEWS! This 4 bedroom, 2 bath home is what you have been waiting for! Updated furnishings, washer/dryer, wifi, window a/c in each bedroom, and an in ground pool (unheated) will make your vacation memorable. Views of Bass River from your front door. Being one of four...
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    South Dennis, Cape Cod 02660
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely Condo Unit at Ocean Edge Resort in the Village of Chilton in Brewster with 2 bedroom, 2 new bathrooms located in lower level garden villa overlooking the green just a short distance to Fletcher Indoor/Outdoor Pool complex, now with WIFI internet! This warm feeling and comfortably decorated...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully Air Conditioned, King, Queen & 2 Twins & 6 Pool Passes (Fees Apply) 'Ready to Rent' This nicely decorated and well maintained Trevor Village A-sytle townhome features 3 split A/C systems giving it a fully air conditioned cool feeling. Guests will appreciate the central location and...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Dennis, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2.5 bath home is what you have been waiting for! Property was recently purchased. New furnishings, fresh paint, washer/dryer, wifi, window a/c in master bedroom, and in ground pool will make your vacation memorable. Home is at the end of a cul-de-sac abutting conservation area,...
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    South Dennis, Cape Cod 02660
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Edge Upper Level with King Bed, 1 AC & 6 Pool Passes (fees apply) This well decorated and maintained Eaton Village home is an upper level apartment offering 2 bedrooms and 2 baths. The kitchen is well equipped with a dishwasher and a washer/dryer. The bedrooms and living room all have flat...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This nautically-inspired 2 bedroom/2 bath garden level condo located in the Village of Eaton in Ocean Edge is the perfect getaway. The unit is impeccably and comfortably furnished. And it’s situated within walking distance to Fletcher or Arbor pool complexes as well as the tennis courts and the...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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