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South Orleans Holiday Homes

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    Travellers to South Orleans are booking July dates now. Secure your holiday 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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    South Orleans
    5 Bedrooms, 2 Bathrooms, Sleeps 10 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
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    Topside BoatHouse on Pleasant Bay1 / 10
    (1)Excellent
    South Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 2016
    I stayed here on my honeymoon many years ago, and have returned every year since then. I could roll out of bed, onto the deck, and into the water without walking 5 steps...
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    About this property
    The BoatHouse is unique. Built and furnished in Cape Cod Cottage style, it sits literally right on Pleasant Bay with deck and stairs leading into the water. In the master bedroom look out across Pleasant Bay before you get out of bed. Full bathroom inside and delightful outside shower. Lounge,...
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    South Orleans, Cape Cod 02662
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    About this property
    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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    52 Forest Way 184231 / 18
    (2)Very good
    South Orleans
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
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    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
    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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
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    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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    South Orleans
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    • 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
    Holiday Rental House - 3 Bedrooms, 3 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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    South Orleans
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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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, 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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    The following rentals are within 10 kilometres 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
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 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 10 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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    North Chatham
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
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    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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    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
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    • 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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    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
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    • 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 / 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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    • 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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    Location Information
    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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 5 weeks ago
    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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    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
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    • 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 3 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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    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
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 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
    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
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    • Cable/satellite TV
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    • Ocean Views
    • Waterfront
    • Washer
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    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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    East Orleans
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • 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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    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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    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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    South Chatham, Chatham 02659
    Holiday Rental House - 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 12 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 10 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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    Brewster
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brewster
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    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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    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
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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 22 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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    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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    Waterfront on Black Pond and Long Pond1 / 24
    (1)Excellent
    Brewster
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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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    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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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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    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 April 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
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 16
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    North Chatham
    2 Bedrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $1325 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT Quaint two bedroom cottage surrounded by beautiful gardens! Located in lovely North Chatham, this little...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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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
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    • Outdoor Dining Area
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    Reviewed 12 July 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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    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    14 Iyanough Road 808401 / 15
    (4)Excellent
    East Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2013
    This is the best maintained rental I have been in. Small, but you can tell the owner really cares about the comfort of her guests—house is clean and well cared for, kitchen well...
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    14 Iyanough Road (ID #80840) ~ Oceanside 2 bedroom charming cottage ~ Nauset Heights 2019 Rental Season! Charming cottage in Nauset Heights just a short distance to Priscilla Landing & Nauset Beach! Great for summer swims, kayaking, shell hunting, and other recreational activities. A patio...
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    East Orleans, Orleans 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Private Garden
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house has been beautifully updated...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    59 Gibson Road Rear Cottage (ID# 18015) ~Central Air~ Town Cove Area ~ 2018 Season! Every reservation includes 2 Lobsters and a Bottle of Wine Complementary! This recently renovated 2 bedroom, 1 bath cottage is nicely appointed in a prime East Orleans location, convenient to Nauset Beach on the...
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    East Orleans, Orleans 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    251 Seaway Brewster 1211231 / 14
    (1)Excellent
    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 6 October 2015
    This location is superb. Views are spectacular. The beach is great even in the fall. Great for walking. Living space (kitchen, dining room and living room) are upstairs and very...
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    251 Seaway Brewster (ID# 121123) ~ Pineland Private Beach Association 2018 Season! Air conditioned beach house, four large bedrooms, and two full baths. Sleeps 8 with two queens, and 4 twins. 100 yards to private Pineland Park Association beach. Custom upside-down design provides great views of...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Brewster
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Newly Updated Brewster Cottage, 150 feet from Private Beach, Linens Included Prime summer weekly rates: $2,500-$2,900 Rents Saturday to Saturday during peak season The new owners of this adorable cottage have completed many upgrades to give the cottage the classic Cape feel with all the modern...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Unit #5 396591 / 14
    (3)Very good
    East Orleans
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 4 September 2012
    had a wonderful stay ,location, westher , cottage great for our needs ..... love orleans and love nauset beach
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    170 Beach Road Unit #5 (ID# 39659) Cottontail Cottage ~ Central Air ~ East Orleans 2018 Season! This cute unit is the left hand side of a duplex in a quaint cottage colony, Cottontail Cottages on Beach Road in East Orleans---less than 1/2 mile to Nauset Beach! Each side has central air...
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    East Orleans, Orleans 02653
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East Orleans
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
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    29 Nauset Road, East Orleans, MA (ID# 18082) ~ Nauset Heights 2018 Season! 'The White Heron' is a wonderful and large Nauset Heights home just steps to Nauset Beach! Spectacular views of the ocean and gorgeous sunrises are enjoyed from every room and both decks! The main floor includes a spacious...
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    East Orleans, Orleans 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Housekeeping Included
    • Shared Indoor Pool
    • Sauna
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    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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    On the Dunes Overlooking Cape Cod Bay1 / 17
    (2)Average
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located atop the dunes overlooking Cape Cod Bay this amazing home is the answer to your vacation wish list. You will enjoy a private stretch of sandy beach near Ellis Landing, gorgeous views of the bay from Plymouth to Provincetown...this is a dream cottage! Main level is very welcoming with a...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Shared Indoor Pool
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    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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    64 Great Oak Road 255281 / 16
    (2)Very good
    East Orleans
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
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    64 Great Oak Road, East Orleans (ID# 25528) 4 Bedroon 2 Bathroom Home near vwith tennis court near village of East Orleans and Nauset Beach 2018 Season! Just 1.5 miles to Nauset Beach on the Atlantic Ocean and close to the Village of East Orleans, this wonderful vacation home has a private tennis...
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    East Orleans, Orleans 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Smoking allowed
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    6 Cedar Land Road, East Orleans (ID#18315) 2019 Season! Adorable home in East Orleans 6/10 mile to Nauset Beach with central air conditioning. This 2 bedroom/1 bath home features an open kitchen/living room and den/TV room leading to the deck and back yard. The bedrooms are furnished with 2 twins...
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    East Orleans, Orleans 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    East Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    31 Fox Ridge East Orleans (ID#18334) Briar Springs-Barley Neck Area 2018 Season! This lovely L-shaped ranch with Central A/C is bright and airy. The kitchen, dining and spacious living area is an open floor plan with a cathedral ceiling. The three-season room off the living area is enclosed with...
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    East Orleans, Orleans 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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