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South Chatham Holiday Rentals

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    Travellers to South Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 43 Rentals in South Chatham
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    2017 Rental Rate: $2775 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Lovely, updated condo with water-views of the Nantucket Sound. Light and bright with comfy upscale furnishings. Located on a quiet side street in...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    cape cod charming family friendly chatham cottage .01 mile to Cockle Cove Beach1 / 22
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 11 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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $3000 per week including the cleaning fee Off-Season Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy, light and bright decor. Finished walkout lower level is the perfect extra...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $1675 per week, including the cleaning fee Off-Season: $975 per week, including the cleaning fee Light and bright 4 bedroom home on quiet cul-de-sac in South Chatham. Comfortable furnishings throughout. Large upstairs bedrooms offer extra seating space too! Nice back deck off the...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Vacation Spot Right up the Road from Pleasant Street Beach in South Chatham! Well appointed and comfortable, this home is convenient to all the area has to offer. Enjoy grilling on the deck in the private backyard after a day enjoying summer on Cape Cod! Four bedrooms and 2 1/2 bathrooms...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (30)1 / 14
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 4 September 2016
    we were searching in a limited area....this fit all of our requirements....4 sleeping areas, large living space, not on main road, quick walk to the beach(car not needed...
    Reviewed 19 August 2016
    Location was very good; close to beach, restaurants and mostly centered to other towns on the cape. Home was clean and easily accommodated our family of 5. Kitchen was stocked...
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    About this property
    Enjoy your Chatham vacation in this 3 bedroom, 2 bathroom house that is only 2/10th of a mile from Pleasant Street Beach on Nantucket Sound. This traditional Cape home features 2 bedrooms on the first floor and 2 bedrooms on the 2nd floor. The living room and kitchen lead to a second light and...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rates: $2600 including the cleaning fee. Off-Season: $1600 including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Wonderful, light and bright summer home located just steps from Taylor's Pond, the Eel River and the warm waters of the Nantucket Sound. Even better, there is a...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    15 Bobbies Lane 430701 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    15 Bobbies Lane CHATHAM Charming and Updated Cottage in South Chatham! A/C, convenient to shopping, beaches, and golf. Only 1/2 mile to Nantucket Sound. Screened in Porch, WiFi, 1 Queen, 2 singles and 2 Queen Sofa beds. Sleeps 6. $1250 per week * $100 Handling Fee * Choice of $55 Damage...
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    South Chatham, Chatham 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    2018 Rental Rate: $3625 per week, including the cleaning fee Off-Season: $2525 per week, including the cleaning fee Wonderful waterfront home, right on Taylor's Pond! This spacious home is light and bright, filled with upscale furnishings, colorful decor, and offers a private, peaceful setting in...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    South Chatham Cape Cod Vacation Rental (8975)1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 23 August 2017
    From the location to the cleanliness of the house, we were impressed. Really having such a wonderful space, and every amenity including chairs and umbrella made our stay on the...
    Reviewed 13 September 2016
    We stayed in this beautiful multi-level immaculate home and enjoyed every bit of it: from the wonderful, spacious, modern kitchen with it's many windows facing the ocean, to...
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    About this property
    Great views of Nantucket Sound from this 3 bedroom, 2.5 bathroom Chatham cottage. This is a newer house with multiple furnished decks and balconies as well as a covered porch and is just a stones throw to a semi-private beach on Nantucket Sound. The master bedroom is detached from the main house,...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There is a sunken dining room off the main living room that opens to a furnished patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath, wet-bar area, two sleep-sofas...
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    South Chatham, Chatham 02695
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    19 Glendon Way, S. Chatham Casual knotty pine summer cottage just 1/2 mile to Pleasant Street Beach. This 3BR/1BA single level cottage is located in a nice quiet neighborhood of South Chatham. Convenient to shopping - just a 10 minute drive into town. $1000 per week * $100 Handling Fee * Choice of...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    #602 - Port View Home1 / 24
    (1)Excellent
    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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    #602 Port View Home: Nantucket sound awaits you in this sweetie beach house. Pull in the driveway, look to the left ... All you see is OCEAN. Magnificent Nantucket Sound with white sandy beach just waiting on you to put down the beach blanket and take a dip! Port view home offers great living space...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Our highly rated & reviewed 3 bedroom 1 & 1/2 bath home is nestled on a quiet side street just 3/10 tenths of a mile from one of the best beaches in Chatham...Forest Beach. Our comfortable home is 1100 square feet; and is updated & modern with Air Conditioning, Wi-Fi & a 50'' LCD TV... yet it...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lovely home with a/c near Ridgevale Beach RIDGEVALE BEACH 7/10 of a mile on Nantucket Sound!! Comfortably sleeps 10!! Cape Cod Bike Trail 8/10 of a mile away. Located at the end of a cul-de-sac and approximately 2 miles to the Village of Chatham for great dining, shopping, Cape Cod League Baseball...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charming 3 bedroom, 1 bath cottage with views of Nantucket Sound from the rooftop deck. There is a good sized backyard and Forest Beach is just 3/10ths of mile away. Amenities include a window AC unit in each bedroom, cable TV (with basic cable only; no NESN, ESPN, Weather Channel, etc.) with a DVD...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    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, WiFi, a screened in porch, 3 spacious bedrooms, and open concept living will make you feel...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 15 in comfort. Kids will love the basement entertainment and sleep area, and you’ll adore the 3-season room. Walk to Forest Beach, and drive to downtown Chatham in 10 minutes! INSIDE THE HOUSE From a drive with parking...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    This gorgeous sprawling home on 3 acres is surrounded by 50 acres of conservation land. It is extremely private, very quiet, has its own pond, and plenty of space for sunbathing and outside play, large, expansive decks, lots of room for entertainment inside and out. It is completely equipped with...
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    South Chatham, Chatham 02659
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3BR, 2BA S. Chatham Family Home. Views of Nantucket Sound – Walk to Beach1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 4 October 2017
    We loved our stay! My wife and I visit Chatham almost every September and this year we took my wife's' parents (80 and 84 yrs old). This was perfect for all of us!The view, the...
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    This 3BR,2BA S Chatham home (sleeps 8) offers beautiful views of the river and marsh, plus a location steps away from family-friendly Cockle Cove Beach and a short drive from dozens of popular Cape destinations. INSIDE THE HOUSE Park in the driveway and enter through a front door into the main...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4BR South Chatham House in Cape Cod!1 / 25
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Begin your Cape Cod adventure by staying in this beautiful 4-bedroom, 3-bathroom saltbox home. Surrounded by natural beauty and close to everything the Cape has to offer, this home is a perfect choice for a group of friends traveling together or a family getaway. Your whole group will love calling...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    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 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Roll out of bed and onto the shore of one of the most beautiful beaches on Cape Cod! Hardings Beach is miles of fun, family friendly, coastline and this beautiful classic turn of the century Chatham rental house is located less than 3 minutes walk to the sand! This charming turn of the century...
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    South Chatham, Chatham 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 12 September 2017
    Our stay at Pleasant Forest Shores was awesome! The cottage was very clean, had a sizable living room & kitchen and was located within a quiet neighborhood. It was also about...
    Reviewed 1 July 2017
    We actually stayed in cottage #2 but they appear to fairly similar. I used to vacation in Chatham as a kid in the late 60's and early 70's. These cottages are VERY reminiscent...
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    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to Forest Beach Cottage. This Cape Cod Vacation home rental in Chatham is just yards out of the back door to Forest Beach. Central AC for those hot summer nights. You can smell the salt water from this ranch-style home with four bedrooms, two baths, and an outstanding family room. (Small...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 22 September 2017
    I admit I ended up here somewhat by accident, but it was a fortuitous accident. Not only is this small cottage colony (5 cottages) perfectly located to get to a variety of...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    About this property
    Come enjoy our spacious 3-bedroom, 2.5 baths home that is just a short walk to Forest Beach and the warm waters of Nantucket Sound. Our home is located on a quiet lane 0.4 mile to the beach, 0.5 to the Cape Cod bike trail, and less than 4 miles to shopping and eating in quaint Chatham Center and...
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    South Chatham, Chatham 24151
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Cape Cod Pine Grove Cottage - 1/2 mile from beach!1 / 15
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2014
    We loved being so close to Cockle Cove Beach. The outside shower was a hit, too. My two teenaged boys loved, loved, loved this place. It would be even better if it had wifi.
    Reviewed 25 August 2014
    I was so happy with our stay! the cottage was very cute and was just enough room! it was close to just about anything you can want to do in the cape. the welcome gift was very...
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    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes....
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to Sea Mist! Spacious Cape Cod Beach House with Central AC and WiFi. Steps to the ocean with deeded access to private beach. Relax and unwind at this 3 bedroom, 2 bath home in Chatham sleeping 6. Enjoy the decks, outdoor shower, and especially the hot tub! Light, bright, and airy. This open...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    Yes, the price is low but that's why so many customers have come for decades! So wanting for a nice clean quiet apartment unit close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    Brand new custom built beauty in South Chatham with water views (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $7,400 - $8,900 Rents Saturday to Saturday during peak season Be among the first to vacation at this wonderful custom-built home in South Chatham. Just finished in...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    2 BR, 1 Bath newly renovated walk/bike to beach and restaurants Renovated in 2017. Our Chatham home is walking/biking distance (0.7 miles) to Forest Beach, Cockle Cove Beach and Pleasant Beach, churches, restaurants, library and the Cape Cod Bike Trail, making it an ideal summer getaway. The...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Charming 4 Bedroom Cape House in a quiet setting that sleeps 10 (5 queen beds). Two good sized family rooms and a spacious back deck provide plenty of space for the family to spread out (complete with outdoor shower) . Easy walk (~ 10 mins) to two beaches (Forest & Pleasant Street). Additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    #607 Whale's Tale: 2-min walk to beach! Water Views from 2ndFloor Master. Private garden and patio! Awake to stunning ocean views from the master bedroom and enjoy morning coffee overlooking the sea from the upstairs balcony, stroll down to the beach or take a ride into nearby downtown Chatham for...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lovely 4 bedroom home less than 300 yards from Forest Beach on Nantucket Sound! Charming 4 bedroom, 2 bath home just 300 yards to Forest Beach on Nantucket Sound! A very comfortable one level home featuring central air conditioning, two separate living areas, a renovated kitchen and a lovely patio...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    2018 Rental Rate: $1675 per week including the cleaning fee. This is a FRIDAY TO FRIDAY RENTAL. ~~ Off-Season: $1275 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Adorable, updated rental located on a quiet street in South Chatham. New furnishings and fresh paint make...
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    South Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    #606 Chatham Charmer: GAME ROOM! Brand new! Large backyard w/deck. 10-min walk to Nantucket Sound beach! Two good sized family rooms and a spacious back deck provide plenty of space for the family to spread out (complete with outdoor shower.) Easy walk (~ 10 mins) to two beaches (Forest & Pleasant...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    #608 Chatham Breeze: Huge yard, large grills, beautiful kitchen, unique vaulted dining! This beautiful architectural home and fully manicured estate has plenty of Cape Cod charm and comfort making it a wonderful place to enjoy a vacation in our seaside community. Located on a quiet cul-de-sac...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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