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South Orleans Vacation Rentals

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    Travelers to South Orleans are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 292 Rentals in South Orleans
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    Large House On Private Acre - Newly Remodeled & New Furnishings1 / 16
    (1)Excellent
    South Orleans
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Topside BoatHouse on Pleasant Bay1 / 10
    (1)Excellent
    South Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    #703:  Estate like home! Waterfront! Chef’s Kitchen & water-top deck!1 / 31
    (1)Excellent
    South Orleans
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    South Orleans
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    5 BR | 2 BA | Sleeps 10 This charming remodeled antique home is only 2/10ths of a mile to a Pleasant Bay beach and a short distance to the five star rated Wequassett Resort. The interior has a brand new kitchen with granite counter tops, stainless steel appliances, wide pine floors and opens up to...
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    South Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    South Orleans
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your kayaks!!! Wonderful vacation home in very exclusive South Orleans neighborhood with a private path to Pleasant Bay private Beach. Home is multi-level with an open floor plan for family entertaining and designed for privacy. Upstairs level includes a living room (with sofa bed), dining...
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    South Orleans, Cape Cod 02662
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Orleans
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Balcony
    • Ocean Views
    • Patio
    • Waterfront
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Six feet of plush lawn separate the MainHouse from the waters of Pleasant Bay. The large garden has plenty of quiet places for reading, relaxing and/or snoozing in the shade or in the sun. Swim or fish from the dock or the nearby beach. Arrangements for a boat mooring are possible. Off-street...
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    South Orleans, Cape Cod 02662
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    South Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Pet Friendly! Spacious family Cape Cod Vacation Rental home in Harwich with A/C, free WiFi, and all the comforts of home. Enjoy a farmer's porch in a peaceful setting with landscaped gardens and yard. It has 3 bedrooms (sleeps 8), 2 baths, and has a lower level that is complete with bar, TV and...
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    South Orleans, Cape Cod 02645
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    52 Forest Way 184231 / 18
    (2)Very good
    South Orleans
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    52 Forest Way, Orleans MA (ID# 18423) 2018 Season! Contemporary home with lots of space, nestled in a quiet wooded area of Orleans. This home is ideal for a casual vacation. 5 Bedrooms (2 Queens, 1 Double, 4 Twins) and 3 Baths. No Pets Accepted. Weekly Rental (7 Night Minimum in Season) _Rent:...
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    South Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Smoking allowed
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    Exquisite Custom Built 5BR Home in Orleans, Tons of Stuff for the Kids! (linens included) Peak Summer Weekly Rates: $6,800 Rents Saturday to Saturday If you're looking for upscale accommodations yet plenty for the kids to do, this stunning new home is the one for you. Situated on a quiet...
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    South Orleans, Cape Cod 02662
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    South Orleans
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Home with Large Private Deck and Hot Tub Overlooking Pond. Peak Summer Weekly Rates: $2,950 - $3,800 Linens Included Rents Sunday - Sunday during peak season If you love nature, privacy and water views this comfortable home is for you. You will wake up each morning to find the water...
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    South Orleans, Cape Cod 02662
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Yard
    • Washer
    • Internet Access
    • Cable/satellite TV
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    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to Pleasant Bay, close to downtown Orleans and Chatham Bring the family together for a memorable summer vacation at this spacious, well appointed home in South Orleans. Filled with natural light and wonderfully furnished with hardwood and tile floors throughout, this 5 bedroom is also...
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    South Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Orleans
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As a vacation rental, this exquisite 5 bedroom/3 full bath home in South Orleans hits all the right notes exactly on pitch. It is both elegant and relaxed, with plenty of indoor and outdoor space to comfortably accommodate 10 guests. The front door opens directly into a living room which is...
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    South Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Orleans
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    22 Little Bay Rd (ID #18416) ~ Oceanside with gorgeous views of Little Pleasant Bay~ 5 Bedroom Home 2018 Season A striking contemporary home only 300 yards to an association beach on Little Pleasant Bay and located in the prestigious East Egg neighborhood of S. Orleans. Open, bright, and very...
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    South Orleans, Cape Cod 02653
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    South Orleans
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    9 Woodridge Road (ID# 99912) ~ Bayside 4 Bedroom Home ~ Pleasant Bay Area 2019 Season! Enjoy a Cape Cod vacation. This 4 Bedroom, 2.5 bath home includes a finished basement great for entertaining and access out to the outdoor shower. There are two Bedrooms and a full bathroom on each floor. All 4...
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    South Orleans, Cape Cod 02653
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    The following rentals are within 5 miles of South Orleans.
    Cape Charmer Near Private Beach!1 / 20
    (2)Very good
    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Patio
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    • Private Yard
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2017
    Wonderful location with the beach a short 3 minute walk away. This home is inviting and comfortable with plenty of room for our family of six. Our contact owner while renting...
    Reviewed August 9, 2016
    This is what it says - a charmer. Lovely wood panelled home surrounded by very large grounds and very, very close to the beach. Yes it maybe a tad old fashioned in parts for...
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    About this property
    Nestled on three lots in private association, only minutes walk from private beach. Perfect for guests to enjoy high and low tides on Cape Cod Bay, finishing the days with brilliant sunsets. Centrally located on the Lower Cape, Brewster has quick access to all that a vacation on Cape Cod has to...
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    Brewster, Cape Cod 02631
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cape Charmer Near Private Beach!1 / 22
    (1)Very good
    Brewster
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
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    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2018
    My family and I had a very satisfying and enjoyable vacation at this house during July 2018. All the facilities were excellently maintained and clean. The beach is very close...
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    About this property
    Nestled on three lots in private association, only minutes walk from private beach. Perfect for guests to enjoy high and low tides on Cape Cod Bay, finishing the days with brilliant sunsets. Centrally located on the Lower Cape, Brewster has quick access to all that a vacation on Cape Cod has to...
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    Brewster, Cape Cod 02631
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (3)Excellent
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 13, 2018
    Great house—-convenient to beach and all Chatham attractions— very responsive owner— comfortably furnished and super clean— great vacation!
    Reviewed September 30, 2016
    We had a lovely weekend here while attending a family wedding. The house was comfortable and equipped with everything a family might need. The neighborhood is quiet and an...
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    About this property
    This bright and airy family-friendly home is just a 1/2 mile walk to this fabulous sandy beach where you can enjoy swimming both on Nantucket Sound or in the milder waters in the adjoining tidal creek. Ridgevale Beach is one of Chatham's most popular destinations for vacationing families. A clean,...
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    Location Information
    West Chatham, Chatham 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated kitchen with quartz “Sea Glass” countertops, backsplash and Nantucket farm sink. Truly a well equipped cooks kitchen. This year round low allergen, open concept home has 3 bedrooms, 2 newly updated baths, a large two level outdoor deck with electric retractable awning, creating a...
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    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beautiful marsh and bay view, secluded beach behind marsh1 / 15
    (2)Very good
    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2014
    The grounds of the home in back are lovely however the interior has not been well miantained; mattresses old and ultra firm, rugs worn, window blinds old and cannot be adjusted...
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    About this property
    West Brewster- Rte 6A -Attractive two story renovated antique barn overlooking serene setting, entire back of house is glass windows- Fabulous views from main living room area and outside deck include Quivett Creek marsh, Cape Cod Bay and hundreds of acres of protected land. secluded Beach access...
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    Brewster, Cape Cod 02631
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Walk to Beach, Beautiful Brewster Home! Crosby1 / 52
    (4)Very good
    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Wi-Fi
    • Washer
    • Patio
    • Porch
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 28, 2017
    Great proximity to the beach, only a 5 min walk for the family. New outdoor shower is great after a lazy beach day. John was very responsive for checkin and questions. Even...
    Reviewed July 21, 2016
    The house was spacious, clean, and perfect for a family get together. Everything we needed was provided, the host was responsive and welcoming. The location was perfect! An easy...
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    About this property
    Very close to the beach for family & pet friendly fun! This magical 4 bedroom 2 bathroom home on a quiet cul-de-sac on Cape Cod in the Sea Captains' town of Brewster. Close to everything including directly across the street from Nickerson State Park and the bike trail. Enjoy lazy summer days in the...
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    Location Information
    Brewster, Cape Cod 02631
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Grill
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2017
    Our stay at Pleasant Forest Shores was awesome! The cottage was very clean, had a sizable living room & kitchen and was located within a quiet neighborhood. It was also about...
    Reviewed July 1, 2017
    We actually stayed in cottage #2 but they appear to fairly similar. I used to vacation in Chatham as a kid in the late 60's and early 70's. These cottages are VERY reminiscent...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    Location Information
    South Chatham, Chatham 02659 1525
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    North Chatham
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
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    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to ChathamBeachCruiser! Relax in our 5 bedroom home with central air. The entire house is equipped with all new furniture in June of 2016 and a few antiques (including a coffee table made from a real ship’s wheel). The house sits at the end of a private drive with plenty of parking. This...
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    North Chatham, Chatham 02650
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Brewster
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
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    • Cable/satellite TV
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    • Ocean Views
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For rent is a 4 bedroom oceanfront house in Brewster, MA. The high tide mark is about 40 feet from face of house, no obstructions or trees to the view. Brewster is the site on the Cape where the tide goes out almost a mile at dead low tide. This exposes sandbars and tide pools which are great fun...
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    Brewster, Cape Cod 02631
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Spectacular Beach Front Home on Cape Cod Bay1 / 24
    (7)Very good
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2016
    This cottage had it all for us. Amazing sunsets, beautiful beach, great location!And a dishwasher. What more could I ask for!
    Reviewed June 2, 2016
    We love this house! Perfect - house is comfortable, well maintained, spectacular setting. Loved the incredible view over Cape Cod Bay, walks along the beach, watching the oyster...
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    About this property
    Located atop the dunes overlooking Cape Cod Bay in Brewster MA this amazing home is the answer to your vacation wish list. Recent renovations include new washer/dryer, fresh paint, new décor and linens, wireless internet and cable. Weeks still available in July, August and September. You will enjoy...
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    Brewster, Cape Cod 02631
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    cape cod charming family friendly chatham cottage .01 mile to Cockle Cove Beach1 / 22
    (1)Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Outdoor Dining Area
    • DVD Player
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    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2016
    We absolutely loved our stay at this charming seaside home, it feels like someones primary residence not a rental. The home is bright, open and beautifully appointed, plenty of...
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    About this property
    0.1 mile from a popular summer Nantucket Sound beach… can walk or ride or /access to private beach via path along marsh just steps away from the house quiet family area… ranch / cottage style house with summer beach flavor with views of Taylor Pond 1 bathroom / eat in kitchen / deck / Weber gas...
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    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream1 / 21
    (6)Excellent
    East Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
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    • DVD Player
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This charming and beautifully renovated cottage was beyond expectations. Great quiet location close to restaurants, beaches and shopping. Jim and Barbara made us feel at home...
    Reviewed September 10, 2018
    Close to Skaket Beach and Orleans, latter for great food. Beautiful house, and so comfortable. The porch is fantastic as is the outside shower. The location cannot be beat - we...
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    About this property
    Our East Orleans cottage has been thoughtfully and lovingly restored, with many unique details. The cottage is bright and airy, and has classic features, including beadboard ceilings, ship lap walls, restored pine floors and classic built-ins. The open living area has cable TV and wi-fi and is...
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    Location Information
    East Orleans, Orleans 02653
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hydrangea House with Cape Charm Near Seymour Pond1 / 13
    (5)Excellent
    Brewster
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Wi-Fi
    • Hot Tub
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 19, 2018
    Great sized holiday home with everything you would need for a holiday. Super sized rooms, plenty of garden & beach chairs and umbrellas. Very well appointed kitchen. Lots of...
    Reviewed July 18, 2015
    My family and extended family total 10 people including my 2 year old nephew stayed here July 11-18th and we had a blast! This house is truly charming with its different decor...
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    About this property
    We rent our property by the week, Saturday to Saturday. This bright attractive home in a lovely, residential setting features something for everyone in your vacationing group... For the gourmet: a fun, light, stainless and Corian kitchen, fully equipped with appliances, butcher block island, gas...
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    Brewster, Cape Cod 02631
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    Reviewed September 24, 2017
    Would totally stay here again. Super clean & comfy, plenty of room for 3 adults & a dog, nice quiet neighborhood with friendly neighbors, close to beach. Had one small...
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Location Information
    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Townhouse in Brewster, Ocean Edge Resort1 / 14
    (11)Excellent
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Hot Tub
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 11, 2016
    Charming unit, very clean, and exactly as described, we loved it.Great communication with the owner; Quick follow-up on our questions / transaction process.We enjoyed our stay...
    Reviewed November 9, 2015
    We usually don't go twice at the same place two years in a row, but for the first we might. My 7 years-old girl, 5 years-old boy, my wife and I loved it. The pools are success...
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    About this property
    - 2 bedroom C-style townhouse in Ocean Edge Resort. 1 1/2 baths, AC, HDTV, Wi-Fi, free phone, washer & dryer and dishwasher. - Private patio with BBQ grill. - Resort swimming pools, whirlpools, fitness center and amenities access. (passes need to be acquired directly at the resort (2015...
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    Brewster, Cape Cod 02631
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Brewster, Cape Cod 02631
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Open & Bright, Clean & Comfy Home Close to beach!1 / 14
    (3)Excellent
    Brewster
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed August 13, 2014
    Stayed here for a week and could not have been more pleased. Location in perfect, house is amazing and owner very helpfull....will definitely been contacting them again next...
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    About this property
    Nice and quiet, clean and updated, 3 bedroom, 2.5 bathroom house is close to wonderful restaurants, great shopping, Cape Cod National History Museum, Brewster General Store and best of all 5/10ths of a mile to Saint's Landing Beach! The master bedroom with queen bed and full bathroom are downstairs...
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    Brewster, Cape Cod 02631
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Minutes to Bay Beaches, Blueberry Pond, Bike Trail, and Ocean Edge Resort1 / 38
    (2)Excellent
    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
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    Reviewed October 6, 2017
    Our family thoroughly enjoyed our trip to the cape,and our stay at the house on Blueberry Pond! The area is beautiful, and the house was very accommodating. There was room for...
    Reviewed October 2, 2015
    This two story home has a downstairs bedroom which is great for those challenged by stairs. The home is in a very quiet area and not hard to find, although a GPS makes that...
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    About this property
    Bike the trail, kayak on the pond, or walk and sun on the bay from this great family house. Newly decorated, spacious, bright, and clean home located in beautiful Blueberry Pond neighborhood. Only 1.5 miles to Brewster Bay Beaches, .5 mile to Cape Cod Rail Trail and Nickerson State Park, walk to...
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    Brewster, Cape Cod 02631
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed September 22, 2017
    I admit I ended up here somewhat by accident, but it was a fortuitous accident. Not only is this small cottage colony (5 cottages) perfectly located to get to a variety of...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    East Orleans
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Private, beautiful family home located on a child-safe street in East Orleans. Three levels of living for a maximum of 10 people. Plenty of room for all. The deck with dining table overlooking private back yard is located off the kitchen. Outside shower and spacious back yard. Garage is where...
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    East Orleans, Orleans 02653
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Waterfront on Black Pond and Long Pond1 / 24
    (1)Excellent
    Brewster
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Waterfront on Black Pond and Long Pond this cottage has 2 docks. Yes, 2 Docks!! 2 bedroom plus sleeping loft cottage. Inside you will find the charm of Cape Cod from the moment you open the door. Nautically inspired interior design with a focus on maximized use of space, this vacation home is a...
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    Brewster, Cape Cod 02631
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Captain's Haven1 / 16
    (1)Excellent
    West Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Yard
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    Reviewed July 29, 2016
    It was a nice little spot for my boyfriend and I to get away for the weekend. Had no issues with the facilities. Please keep in mind the cabin isn't air conditioned. There are...
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    About this property
    An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, one bedroom with 2 twin beds...
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    West Chatham, Chatham 02633
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Friday to Friday Rental This cottage is converted out of an a barn built in 1792. The upstairs bedroom has a full bed and the downstairs bedroom has a day bed (2 twin beds). This cottage is not for everyone. The entrance to the upstairs bedroom is steep and 18' wide. You can see it next to the...
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    South Chatham, Chatham 02659
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Our home “The Sea Glass” is located off historic Tubman Road in the heart of Brewster. The living room is open to a galley kitchen and a dining area on the first floor. There is a spacious deck off the living room overseeing a large, semi-shaded backyard, a perfect place to sit back and relax after...
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    Brewster, Cape Cod 02631
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Our highly rated & reviewed 3 bedroom 1 & 1/2 bath home is nestled on a quiet side street just 3/10 tenths of a mile from one of the best beaches in Chatham...Forest Beach. Our comfortable home is 1100 square feet; and is updated & modern with Air Conditioning, Wi-Fi & a 50'' LCD TV... yet it...
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    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rights to Brewster's Best Private Beach1 / 14
    (3)Excellent
    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Executive Waterfront Luxury Home. A/C; Heated Pool & Elevator1 / 29
    (1)Excellent
    East Orleans
    4 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 22, 2018
    We just had a glorious week enjoying the incredible views, the majestic house and pool, and of course the natural beauty of the Cape. We have rented our fair share of properties...
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    About this property
    This 6000 sq-ft luxury Estate is a gracious oasis of tranquility with mesmerizing views suitable for family vacations & executive corporate retreats. This luxurious estate features four large Master Bedroom Suites, Elevator, A dinning room that seats 16, Large Living Room, Great Room, Game/Media...
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    East Orleans, Orleans 02653
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 16
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    Brewster
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Upscale Lake Front Home with Spectacular Views and Large Private Deck Peak Summer Weekly Rates: $4,800 - $5,200  Rents Saturday - Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home If you love nature, privacy and water views this comfortable home is for...
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    Brewster, Cape Cod 02631
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Two Bedroom Cape Cod Townhouse at Ocean Edge Resort ~ Perfect Get Away1 / 39
    (1)Excellent
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Shared Indoor Pool
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    • Sauna
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    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 25, 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Brewster
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    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
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Walk 4 Min.to Beach, New Custom Home, New Everything, Linens Included Peak Summer Weekly Rates:  $4,500 - $4,800 Rents Saturday to Saturday This newly constructed home will welcome its first guests in the summer of 2018. The custom home has the highest level of amenities including a gourmet...
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    Brewster, Cape Cod 02631
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Ocean Edge Resort Condo 2 Level, 2 Br, Central AC1 / 24
    (1)Very good
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2016
    We found this a very pleasant place to stay. It offered many amenities-the owners seemed to think of everything. It probably is a good place for a couple and 2 children as the...
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    About this property
    Sleeps 6, Private Patio with Grill, option to purchase Pool and Sports passes Purchase of up to 6 pool and sports passes are available with this property. Please see bottom of the listing for details. This is a clean, family-friendly two-floor, 2 bedroom, 1.5 bath townhouse located in private...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Smoking allowed
    About this property
    Welcome to Summer Oasis! Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9.   A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0.6 mile)! Central air, free WiFi, a screened in porch, 3 spacious bedrooms, and open concept...
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    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    North Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks - $2,000 Rents Saturday - Saturday during peak season Please note:  This property is part of a larger estate, and is only available to rent individually in the months outside of July and August...
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    Location Information
    North Chatham, Chatham 02650
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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