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Holiday Rentals in South Chatham

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    All 43 Rentals in South Chatham
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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, Sleeps 8 Quick View
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    3 Bedrooms, Sleeps 8 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $3000 per week Call About Off-Season Click for More Photos, Map, and Availability Calendar Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy,...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There are two dining areas, one in the kitchen and another off the main living room that opens to a small patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath,...
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    South Chatham, Chatham 02695
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 7 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,175 per week No Off-Season Click for More Photos, Map, and Availability Calendar Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    South Chatham Cape Cod Vacation Rental (30)1 / 14
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 20 August 2018
    Super location 2 minutes walk from beach, old world charming house with 2 bedrooms on ground floor and upstairs sleeps 6 in one large room! Plenty of indoor and outdoor toys for...
    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...
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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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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Please contact Courtney...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,050 per week Off-Season: $1,750 per week Click for More Photos, Map, and Availability Calendar Spacious 4 BR home on quiet street near Cockle Cove Beach. Lots of living space in this private and centrally located home. Minutes from bike trail...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, 3 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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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    About this property
    Welcome to Summer Oasis! Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9.   A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0.6 mile)! Central air, free WiFi, a screened in porch, 3 spacious bedrooms, and open concept...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 8 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $1675 per week Off-Season: $1325 per week Click for More Photos, Map, and Availability Calendar Adorable, updated rental located on a quiet street in South Chatham. New furnishings and fresh paint make this a very comfortable spot for your...
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    South Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,600 per week Off-Season: $1,600 per week Click for More Photos, Map, and Availability Calendar 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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    South Chatham Cape Cod Vacation Rental (12593)1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 4 weeks ago
    The house was clean and in a great location. The kitchen had everything that we needed and more! The house did have a musty smell, but, other than that, it worked well for our...
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    About this property
    There's a path to Pleasant Street Beach just down from this 3 bedroom 2 bathroom cottage. Enjoy a day at the beach and return to relax on the back deck with dining table and both gas and charcoal grills. The kitchen has been beautifully updated with stainless steel appliances. There is a very...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cape Cod / Chatham HISTORIC FAMILY ESTATE1 / 8
    (2)Excellent
    9 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    • Ocean Views
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    About this property
    Southwesterly ocean breezes flow over this HISTORIC family estate built in the 1930?s by Mr. & Mrs. John Peale Bishop, a classmate and best friends at Princeton of F. Scott Fitzgerald and himself a famous writer and poet. The Gatsby sits on 1.3 acres in Chatham overlooking Nantucket Sound....
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    South Chatham, Chatham 02659
    Holiday Rental House - 9 Bedrooms, 4 Bathrooms, Sleeps 20
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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) 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 January 2017, this...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 9
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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 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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    NEW LISTING! Classic home w/deck & yard - walk to Cockle Cove & Forest Beaches1 / 26
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beach-going families will find a welcoming retreat at this three-bedroom South Chatham home, a darling Cape Cod escape with a private deck and patio, a fenced yard, and a wonderful location within a short walk of the beach! This classic home sits a block off Main Street in South Chatham, just...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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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 6
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    35 John Street 990451 / 17
    (1)Excellent
    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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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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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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    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 - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    15 Bobbies Lane 430701 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    15 Bobbies Lane CHATHAM Charming and Updated Cottage in South Chatham! A/C, convenient to shopping, beaches, town tennis 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...
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    South Chatham, Chatham 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    South Chatham Cape Cod Vacation Rental (8975)1 / 21
    (3)Excellent
    3 Bedrooms, 2 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
    ***Price Reduced for Week of 8/25 - 9/1 to $3,000*** 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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,900 per week Click for More Photos, Map, and Availability Calendar Adorable beach cottage located less than 1/2 of a mile to the peaceful shoreline of Forest Beach and a 1/2 mile stroll to 2 great dining establishments, Pieces & The Talkative...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    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. 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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 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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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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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 2 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 26 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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    About this property
    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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    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 10 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, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Private Garden
    Suitability
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book your stay at this updated and spacious 3-bedroom, 2.5-bathroom vacation rental house in the heart of Cape Cod’s best town, South Chatham. Boasting 2,688 square feet of tasteful living space, an outdoor fire pit with ample seating, a wet bar, 2 gas grills and picnic tables, this property is the...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Friday to Friday Rental This cottage is converted out of an a barn built in 1792. The upstairs bedroom has a full bed and the downstairs bedroom has a day bed (2 twin beds). This cottage is not for everyone. The entrance to the upstairs bedroom is steep and 18' wide. You can see it next to the...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Pleasant Forest Shores cottages #4 : So. Chatham1 / 4
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
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    Smoking allowed
    Reviewed 16 August 2018
    Have vacationed at Pleasant Forest Shores the past four summers. Cottages are perfect location for my hobbies and interests. Close to beach, restaurants, golf, and baseball...
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    About this property
    NOTICE: This listing is missing some pix still as created it quickly due to a recent cancellation so look for more pix elsewhere. Yes, the price is very low but that's why SO many customers have come for years/decades/generations and why I have so few openings, ESPECIALLY during the mid-July to...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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 group of 10 friends and family...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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