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Holiday Rentals in South Orleans

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    Travellers to South Orleans are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 303 Rentals in South Orleans
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    Topside BoatHouse on Pleasant Bay1 / 10
    (2)Excellent
    South Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    South Orleans
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    South Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Orleans
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    South Orleans
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Grill
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    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
    Holiday Rental House - 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
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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
    Holiday Rental House - 4 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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    • DVD Player
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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
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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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  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 sparkle over...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 3 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
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • 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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    The following rentals are within 10 kilometers of South Orleans.
    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 13 July 2018
    Great house—-convenient to beach and all Chatham attractions— very responsive owner— comfortably furnished and super clean— great vacation!
    Reviewed 30 September 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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    West Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    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
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 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 9 August 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    • Parking
    • DVD Player
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2018
    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 10 September 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • 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
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Spectacular Beach Front Home on Cape Cod Bay1 / 12
    (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 30 August 2016
    This cottage had it all for us. Amazing sunsets, beautiful beach, great location!And a dishwasher. What more could I ask for!
    Reviewed 2 June 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
    Holiday Rental House - 2 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 19 July 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 19 July 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Walk to Beach, Beautiful Brewster Home! Crosby1 / 26
    (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 28 December 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 21 July 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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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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 11 January 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 9 November 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
    Holiday Rental House - 2 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 29 July 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    North Chatham
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to ChathamBeachCruiser! Relax in our 5 bedroom 4.5 bathroom 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...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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 Garden
    • Grill
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East Orleans
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • Private Garden
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    • Air Conditioning
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    Smoking allowed
    Reviewed 25 September 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    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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    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Classic home w/ deck, patio & yard - walk to Cockle Cove & Forest Beaches!1 / 26
    (1)Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach-going families will find a welcoming retreat at this three-bedroom South Chatham home, a darling Cape Cod escape with a private deck and patio, a fenced yard, and a wonderful location within a short walk of the beach! This classic home sits a block off Main Street in South Chatham, just...
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    Location Information
    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 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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    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Porch
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 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 2 October 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Sauna
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    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
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Kid friendly
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Please contact Courtney...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    North Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $5350 per week (linens also included) Off-Season: $4400 per week (linens also included) for 8/24 to 9/7 - No Other Off-Season Availability Click for More Photos, Map, and Availability Calendar *Weekly Rentals Only* Gorgeous home in high-end...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    North Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Come stay at: Misty Meadow! Enjoy this lovely condo with all amenities including Central AC mini splits and free WiFi Conveniently located too. Situated in a very quiet area of North Chatham offering private conservation views from this charming one bedroom, first floor, end unit condo. An open...
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    North Chatham, Chatham 02650
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Chatham
    3 Bedrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Waterfront
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    Kid friendly
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    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $3000 per week Call About Off-Season Click for More Photos, Map, and Availability Calendar Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy,...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Kid friendly
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Brewster
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    This quintessential beach cottage has views of Cape Cod Bay from the front yard. Gorgeous vacation home just .1 mile to a private association beach on Cape Cod Bay! You will love the screened in porch, a wonderful outside shower, and a simply relaxing and charming atmosphere. Home has 4 large...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Ocean Edge Upper Level Well Maintained with pool (fees apply) - ED02531 / 14
    (1)Excellent
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2014
    Really pleased with the place. Set on a private golf course - very peaceful. Accommodation was well maintained, comfortable and spacious. Nice outside deck off the kitchen.
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    Upper Level, King Bed, Renovated, 4 ACs, 7 Pool Passes (Fees Apply) Nicely renovated Edinborough Village unit features beautiful wood flooring throughout and is a short walk to the Arbor pool complex and The Linx Tavern & Bar. The master bedroom has a king bed, AC, ceiling fan, TV, private deck,...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Orleans
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    26 Tides End Lane, East Orleans MA (ID# 52984) 2019 Season! Waterfront home with private dock on Meetinghouse Pond and access to Pleasant Bay. Casual living with water views from almost every room. Picturesque grounds and a nice sunny porch is just about everything you need to enjoy your Cape Cod...
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    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    North Chatham
    2 Bedrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $1375 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar Quaint two bedroom cottage surrounded by beautiful gardens! Located in lovely North Chatham, this little cottage is just what the doctor ordered....
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    10 Captain Curtis Way 184361 / 17
    (2)Average
    East Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    10 Captain Curtis Way, Orleans (ID#18436) 2018 Season! Cute as a button with Seaside touches and well equipped for your Cape Cod Vacation! Located on a lovely, quiet street with easy access to Nauset Beach and the Village of East Orleans. Living/Dining/Kitchen Area is centrally located with 2...
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    East Orleans, Orleans 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    North Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Smoking allowed
    About this property
    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 miles to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 1 mile to Main St., Chatham for shopping,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Upper Level, Golf Access, King Bed, 4 ACs, 7 Golf & Pool Passes (Fees Apply) This spacious, Endicott Village apartment is just steps to the Arbor Pool, the Golf Clubhouse and the Linx Tavern & Bar. The master bedroom has a king size bed, AC, TV, deck and private bath. The 2nd bedroom has a queen...
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    Brewster, Cape Cod 02631
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    • Air Conditioning
    • Housekeeping Included
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    North Chatham
    5 Bedrooms, Sleeps 11 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $5350 per week (linens included) ~ June 22-29 and August 24-31: $4400 per week (linens included) Click for More Photos, Map, and Availability Calendar Gorgeous home in secluded North Chatham neighborhood. The home features hardwood floors, WiFi...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    South Chatham
    4 Bedrooms, Sleeps 8 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $2,150 per week Off-Season: $1750 per week Click for More Photos, Map, and Availability Calendar Spacious 4 BR home on quiet street near Cockle Cove Beach. Lots of living space in this private and centrally located home. Minutes from bike trail...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    Sleeps 10 Near Crosby Landing Beach -- 050-B1 / 30
    (1)Excellent
    Brewster
    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   An 8-10 minute walk from this big and neat-as-a-pin two-story home brings you to sweeping Crosby Landing Beach, considered Brewster's...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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