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Holiday Homes 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 601 Rentals in South Orleans
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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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    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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    South Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    • 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, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Grill
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Vacation Home Near Pleasant Bay in East Harwich! This comfortable and conveniently located home is close to Orleans, Chatham and beaches on Pleasant Bay, and only just about a half mile to Wequassett Resort. Enjoy a morning cup of coffee on the bright and sunny enclosed porch or the private...
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    South Orleans, Cape Cod 02645
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Suitability
    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
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • DVD Player
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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
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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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
    Kid friendly
    Smoking allowed
    About this property
    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 a dining area. There are...
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    South Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
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    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    9 Woodridge Road (ID# 99912) ~ Bayside 4 Bedroom Home ~ Pleasant Bay Area 2018 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, 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 kilometres of South Orleans.
    Nauset Beach and Privacy1 / 12
    (13)Excellent
    Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nauset beach is just down the road from this East Orleans Village, sun filled home. The quiet private road and 150 foot driveway opens into a large backyard, surrounded by privacy, tall Cape Cod pines and colorful flower beds. [NOTE TO ALL INQUIRERS - PLEASE SEE THE HOUSE'S UP-TO-DATE...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    • Grill
    • Patio
    • Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    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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    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (1)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 1 October 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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    Charming Beach Front Cottage on Pvt Beach1 / 12
    (4)Very good
    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Central Heating
    • Grill
    • Balcony
    • Ocean Views
    • Parking
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    I paid a premium price to have a place on the beach and to be able to see the beach and ocean. My view from the deck was totally obstructed by overgrown plants. It was clear...
    Reviewed 11 November 2016
    Vacation was good but still have not received refund of $200 per agreement with owner who claimed that he was entitled to half of the $400 deposit I put down for any damage. Can...
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    About this property
    Waterfront on Cape Cod Bay! Completely renovated beach front cottage with gorgeous views and amazing sunsets. Private stairway to the beach to put your toes right in the sand. Exquisite details inside include hardwood floors and fully equipped Kitchen. The space is perfect for entertaining with the...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Brewster
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Hydrangea House with Cape Charm Near Seymour Pond1 / 13
    (4)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 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
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Porch
    • DVD Player
    • Air Conditioning
    Suitability
    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 3 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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    Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only 1.8 miles to Nauset Beach and located In East Orleans Village! This renovated barn is private and cozy. You can walk into the village to get a morning coffee and newspaper, mail a postcard or grab a fresh made sandwich for your day * the beach. Stroll to dinner * one of the fine restaurants,...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are bright and nicely appointed with...
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    South Chatham, Chatham 02659
    Holiday Rental House - 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 24 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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    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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Secure Parking
    • DVD Player
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, well-appointed home has a huge, eat-in gourmet kitchen, along with a large dining room. It was built in 2002, is modern and very comfortable, with A/C upstairs and down. We've been renting every summer for the last 8 years, and all of our renters have been very happy with the...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, 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 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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    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
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    • Patio
    • Porch
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    • Cable/satellite TV
    • Air Conditioning
    Suitability
    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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    Beagle Nest - Large 5br close to best bay beaches1 / 38
    (6)Excellent
    Brewster
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Patio
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    • Washer
    • Sauna
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2016
    This home is wonderful. It was the perfect setting for our family. Spacious, CLEAN, and Welcoming. Would love to return as soon as possible
    Reviewed 9 August 2014
    This house was a great rental! So much to do, and lots of room! Our son got married on the Cape, so we made a vacation out of it. The groom had the best time from the bar room...
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    About this property
    2016 summer rentals are Sunday through Sunday, check in 4 pm, check out 10 am. Full weeks only in June and August through the end of Labor Day week. Weekend rentals only available off season (April, May, late September, October etc.) 2016 Thanksgiving, Christmas, New Years long weekends - $1500....
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    Brewster, Cape Cod 02631
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Orleans
    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
    Charming remodeled 1930s cottage! This home is located in the desirable and scenic Mill Pond area in Orleans with a well kept yard and wrap-around deck. House is very comfortable with single story living. Three bedrooms (brand new mattresses) and 1 and a half baths are located off the main living...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
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    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 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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    Brewster
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
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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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    Brewster
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Recent first-floor renovation! Beautiful vacation home located in Trevor Village at the Ocean Edge Resort in Brewster, located in Trevor Village this is a two story town-home located just a couple minutes from the Fletcher indoor & outdoor pools. On the first level of this home, you will find brand...
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    Brewster, Cape Cod 2631
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    East Orleans
    6 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    Historic 1860's antique Cape Cod home, perfect for groups or families with kids and/or pets! Located in the Pochet area of East Orleans and just a short distance to Nauset Beach, the charming village of East Orleans, and the clear, warm water at Crystal Lake! This Pet Friendly home is set on over...
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    East Orleans, Cape Cod 2643
    Holiday Rental House - 6 Bedrooms, 1 Bathroom, Sleeps 12
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    Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 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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    Orleans, Cape Cod 02653
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Orleans
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This 2 bedroom condo is equipped with kayaks and canoes right on the association dock. (First come first use with a few other condo units.) Renovations include air conditioning, new hardwood floors, new windows, outside shower, and additional half bath. The main level offers a fully stocked kitchen...
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    Orleans, Cape Cod 02653
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, children's books and videos,...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
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    Pet friendly
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    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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    ESTATE OVERLOOKING PILGRIM LAKE IN ORLEANS! LINENS INCLUDED! DOG FRIENDLY!1 / 41
    (1)Excellent
    Orleans
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Reviewed 8 February 2018
    The house is in a truly idyllic and very private setting. From the deck you overlook the gorgeous lake. When the mood strikes it’s a 30 second walk down to private access for...
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    A FEW PAST REVIEWS: 'The beach area behind the house was heaven sent, it's private, beautiful and easy. We also drove to the ocean which was about 5 minutes away. But we stayed at the house most of the time and had everything we wanted.' 2017 guest 'The house is in a truly idyllic and very private...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Orleans
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    SKAKET BEACH is just 3/10th's of a mile away via path at Willie Atwood Rd and Cape Cod Rail Bike trail access is very close to this splendid Orleans home! This 4 bedroom home with Central A/C is set on almost an acre of land down a sandy lane, steps from Cape Cod Bay and the Cape Cod Rail Trail for...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    On the Banks of Rock Harbor Creek1 / 36
    (1)Excellent
    Orleans
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Located on the bank of Rock Harbor Creek, this 5 BR, 4 Bath classic Cape has all you and your family are looking for this summer. The large second floor master suite overlooks the marsh with an attached private bedroom with 2 twins where the little ones can dream away, close to the folks. There is...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Orleans
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    New bedroom suite, recently expanded living room, flat screen TV's and 2nd full bath! This quaint 3 bedroom, 2 full bathroom Cape Cod Vacation Cottage is located on a spacious corner lot located just 3/10 of a mile from beautiful Skaket Beach in Orleans. Enter into cheerful living room, here you...
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    Orleans, Cape Cod 2653
    Holiday Rental House - 3 Bedrooms, 2 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
    • Cable/satellite TV
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    • Sauna
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    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 January 2018
    Beautifuly furnised and very comfortable.Close to CC bay. Swimming pool and hot tub a plus!A golfers paradise when in season.
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    About this property
    Hello & Welcome to my Two Bedroom - Two Bath Townhouse which is an End Corner Duplex and is located in Brewster on the Premier Ocean Edge Resort & Golf Club Property~Daily and Weekly Sponsored Guest Passes are Available for Swimming Pools - Tennis Courts - Bike Rentals - State of the Art Fitness...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Brewster
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
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    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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    IDYLLIC RETREAT NEAR NICKERSON PARK AND PONDS! PET FRIENDLY!1 / 23
    (4)Excellent
    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2017
    My family spent a week in mid September at this cottage. It was a wonderful time of year since we wanted to avoid the busy "high season". The home is centrally located...
    Reviewed 25 May 2017
    My husband and I spent a fantastic week at this Brewster home with our daughter, son-in-law and 2 granddaughters. The home had everything we needed. It is very spacious with...
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    About this property
    “Warm and inviting cape retreat.” “The house has great amenities including plenty of space for guests to be together without being on top of each other, social kitchen, warm fireplace, and awesome outdoor shower. Close to conveniences and beaches. Great location!” Mlandsman, Copenhagen, Denmark....
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Orleans
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Sweeping Bay Views, Privacy, Two Full Kitchens  (Pets Considered)  Peak Summer Weekly Rates: $4,300 - $4,500 Rents Saturday - Saturday during peak season This unique vacation home is nestled between Rock Harbor to the east and Skaket beach to the west. The home has its own private boardwalk...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Charming 3 bedroom, 1 bath cottage with views of Nantucket Sound from the rooftop deck. Forest Beach is just 2/10ths of a mile away. Amenities include a window AC unit in each bedroom, Wi-Fi, cable TV with basic cable only, DVD player, washer, enclosed outdoor shower, a deck with furniture and a...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Brewster
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This saltbox style home abounds with sunny colors and English Country ambience. The first floor features a super comfortable living room with TV & DVD player, fully equipped eat in kitchen with A/C and ceiling fan, a full bathroom with tub/shower combination, laundry, and a queen size bedroom with...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    NAUSET HEIGHTS! A VERY SPECIAL HOME FOR 6 VERY SPECIAL GUESTS.1 / 26
    (2)Excellent
    Orleans
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 12 July 2017
    My husband, three children and I just returned from an incredible week vacationing here — we only wished we could have stayed longer. Beautifully decorated and well located, the...
    Reviewed 14 June 2017
    This is an excellent location for all Orleans beaches with access to the private resident’s beach which is wide open, clean and just stunning. The property itself provides...
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    About this property
    This beach cottage has undergone a face lift to maximize the exterior and interior space and to completely redefine the meaning of rustic from its 20th century images of musty rugs and knotty pine. The new owners have created an oasis that is simple and multi-functional, all while maintaining the...
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    Orleans, Cape Cod 02653
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Waterfront on Black Pond and Long Pond1 / 18
    (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!! 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 dream come true. The living room is bright...
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    Brewster, Cape Cod 02631
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    2018 Rental Rate ~ $2050 per week, including the cleaning fee Off-Season: $1750 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT 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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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