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Chatham House Rentals

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    420 Matching Rentals in ChathamView all 450 rentals
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Welcome to Harding's Beach Hills, where you will find Three Cheers, this charming cottage by the sea! This Chatham Cape Cod Vacation Rental offers ranch style living with A/C units in all 3 bedrooms, wireless internet, and expanded cable with flat screen TV in both the living room and master...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet Friendly! Located in a prime in-town location. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a few blocks to beautiful Lighthouse Beach. This desirable and newly renovated family compound built by...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Welcome to: Endless Summer. Views-Views-Views! Pet Friendly Cape Cod Vacation Rental home with rooftop deck is just .2 to Ridgevale Beach. Pet friendly! Enjoy water views from the main floor living areas and the upstairs master bedroom rooftop deck. Sit-Relax and breathe while taking in the amazing...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    8 Bedrooms, 11 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    Rising majestically over Eldridge Point, overlooking Oyster River, Harding’s Beach, and Nantucket Sound, this extraordinary estate features the largest private shoreline in Chatham. Watch glorious sunsets while swimming in your infinity edge pool; or cook dinner in the outdoor kitchen while friends...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 8 Bedrooms, 11 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    This landmark property has the most remarkable views anywhere! After a day at the beach relax and take in one of the prettiest views on the Cape. Three bedrooms, bonus sleeping area, one full and two half baths and on a quiet cul-de-sac, at the very end of the road and sitting on just over an acre...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet Friendly! Located in a prime in-town location! This Cape Cod Vacation Rental Cottage complex offers deeded access to the Mill Pond (a saltwater inlet of Nantucket Sound) and is just a few blocks to the beautiful Lighthouse Beach in Chatham's Old Village. This desirable and newly renovated...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    This perfectly situated Chatham rental is welcoming to you and your four legged friends. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to town on sidewalks and enjoy the amazing shops and restaurants. Head to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    241 Training Field Road PET FRIENDLY Charming and updated 3 bedroom air conditioned ranch style home, just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1900 per week in season * $160 Cleaning Fee * $100 Handling Fee * $55 Damage Insurance OR $500 Security Deposit Please contact...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 10 Quick View
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    2017 Rental Rates: $4725 per week, including the cleaning fee Weekly rentals ONLY No Off-Season Walk to the water in minutes from this light and bright 4 BR home located in Harding's Shores! The location is fabulous, and the home features a large private fenced in back yard and enclosed outdoor...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Pet Friendly! Located in a prime in-town location. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a few blocks to the Beautiful Lighthouse Beach. This desirable and newly renovated family compound...
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    Chatham, Cape Cod 02633
    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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    • Wi-Fi
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    Pet friendly
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    About this property
    Welcome to: Seaside Stroll! Beachfront Condo! 3 Bedrooms, sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor, Little Beach, or bike up to the village of Chatham. Easy bike ride to Lighthouse Beach and Monomoy Wildlife Refuge!  Central AC...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 10 Quick View
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    2017 Rental Rates: $5800 per week, including cleaning fee Off-Season: $4100/wk, including the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Location Location Location! This wonderful, family rental is a short walk or easy bike ride into downtown Chatham and offers swimming/sunbathing...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    3 Bedrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2150 per week, including the cleaning fee Off-Season: $1525 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious three bedroom ranch in quiet neighborhood near Hardings Beach. Recently updated, it is filled with comfortable furnishings and has...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham! Offering Central AC & Wifi - like most of our Cape Cod Vacation Home Rentals - with over 1600 sq. ft. of finished living space, 3 bedrooms, 2 full bathrooms, and a large den there is plenty of space for you to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    • Hot Tub
    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Imagine walking through the front door to a stunning view of the water overlooking Chatham pier and your own heated pool. Relax in the hot tub or sit on the back patio and take it all in. This waterfront vacation home has magnificent views from every angle. With four bedrooms, this sophisticated...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    14 Capri Lane Chatham Cape Cod1 / 28
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Coastal, seaside home offering Central air has plenty of room for 3 couples or 2 families. Walk to beach and town! This Cape Cod Vacation Rental in Chatham has an open floor plan with 3 bedrooms on the main floor and a fully finished lower level game/family room with extra sleeping. Deeded access...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $2100 per week, including the cleaning fee, including the cleaning fee Call about September and October This is a well maintained property located in a quiet area in W. Chatham. Spacious bedrooms, one with two double beds. Updated kitchen, with a skylight, opens to dining area &...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. Located in a residential area and convenient to the Cape Cod Bike trail, and the Chatham Airport and restaurant (Hanger B eatery).  It has 3 a/c units in main floor bedrooms and wifi too....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Come stay at: Seashell Beach Cottage! Beach front vacation rental cottage in Chatham! Stay at this 2 bedroom cottage located right on the beach in Chatham, the best of Cape Cod. Beautiful views! Perfect for a relaxing getaway, this romantic cottage is just steps from the sand, Find your pathway to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Your perfect vacation starts here in this 2017 renovated 4-bedroom home close to Shore Rd and downtown Chatham. Easy walk to restaurants, shops, Oyster Pond, Chatham Bars Inn, Fishing Pier, playground, and A's ball field. Patio with grill, outdoor shower, huge lawn, half basketball court. Both a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    • Private Garden
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    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, Sleeps 10 Quick View
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    2017 Rental Rate: $2825 per week including the cleaning fee ~~~ Off-Season: $2225 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean from large deck. Short walk to...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    When only the best will do, head straight to this indulgent 2BR/2BA vacation rental in North Chatham, where high-end furnishings and an inviting outdoor haven offer a vacation experience that’s second to none. Inside, find granite countertops and stainless steel appliances in the kitchen and...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Lovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated kitchen and an awesome location! The beach is just a walk across the street from this beautifully landscaped Shore Road home. This home is located on the first fairway of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    On the Water! With Central Air and Wireless Internet-Pet Friendly too. Pet friendly for Dogs only-ask your rental specialist for details. This Cape Cod Vacation Rental home in North Chatham has expansive views of Pleasant Bay from both a lower and upper deck, both living areas, the dining room and...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8 Quick View
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    2017 Rental Rates: $2600 including the cleaning fee. Off-Season: $1700 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, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Come stay at: The Cozy Beach Cottage! Chatham Vacation Rental Cottage at the beach! Get away to this 1 bedroom cozy cottage located right at the beach in Chatham, the best of Cape Cod-Sleeps 4. Perfect for a relaxing, romantic getaway, this cottage is steps from the sand, and is ready for your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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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    A "Shore Thing" in Chatham!1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Cape Cod Dreaming by the Beach - Perfect for families to share! Relax by escaping to our newly refurbished and decorated classic Cape Cod cottage, just a short walk, 4/10 of a mile, to sandy Pleasant Street Beach on Nantucket Sound. It is walkable to Forest Street and Red River Beaches. Swim,...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 11 Quick View
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    2017 Rental Rate: $8600 per week including the cleaning fee Off Season: $6650 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    17 Palmer Drive Chatham Cape Cod - The Little Caper1 / 27
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Welcome to The Little Caper. This updated 4 bedroom, 2 bath vacation rental home in Chatham is well maintained and a great spot for making family memories. Just under a mile to town, this coastal Cape is located in a quiet, family neighborhood. The home offers open living with plenty of space to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $2475 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Take advantage of an easy walk to Hardings Beach from this light and bright updated ranch. The kitchen has been opened up with new appliances and finishing touches. There is a fantastic screened in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2300 per week, including the cleaning fee ~Off-Season: $1200 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Light and bright 4 BR home, in a great central location! This recently updated home is across from the school tennis courts and playing fields,...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    61 Eliphamets Lane Chatham Cape Cod - Milhaven1 / 29
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    WATERFRONT! Come stay at: Milhaven, This Cape Cod Vacation Rental is located in Chatham's Old Village and is right on Mill Pond. The Old Village is popular for its historic nature and architectural beauty.  Witness beautiful sunset views from the patio.  It is a short walk to Chatham Village...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beachfront townhome! Sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor and Little Beach. Bike to town or the Monomoy Wildlife Refuge. Central AC and WiFi too. Come stay at: 'Outermost Condo' a coastal 2 bedroom/2 bath townhouse right on...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    2017 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL! ~~ Off-Season: $1400 per week including the cleaning fee !!! Weekly rentals from mid-JUNE to mid-SEPT Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    2017 Rental Rate: $1725 per week, including the cleaning fee ~~ Off Season: $1125 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Parking
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    Pet friendly
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    Smoking allowed
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    Welcome to The Cape Escape! Walk to Hardings Beach from this Chatham Vacation Rental Home. 4 Bedrooms, sleeps 8. Access to association dock and picnic area in Harding's Hills Association.  A/C units in 3 bedrooms and the main living area- there is cable and Wifi too. Calling all beach goers!! You...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    201 Main Street Chatham Cape Cod - Sandpiper1 / 38
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Hot Tub
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    Smoking allowed
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    Experience the Sandpiper! Pet Friendly! Nothing beats this luxury 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! BONUS: LINENS INCLUDED IN SEASON. Whether you are soaking in the hot tub on the private patio or enjoying an outdoor shower after you've come...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 9 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    2017 Rental Rate: $4270 per week including the cleaning fee. Weekly rentals from mid-JUNE to mid-SEPT Charming Cape-style home on Main Street in Chatham's Old Village. Located just blocks from the shops and Lighthouse Beach, this is a great location! This home offers comfortable interior space for...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 9
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    3 Bedrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
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    2017 Rental Rate: $3625 per week, including the cleaning fee ~~~~~Off-Season: $2525 with cleaning fee included ~~~~~ Fabulous updated home located in North Chatham, convenient to town and many of Chatham's beaches! High ceilings & hardwood floors throughout and a screened in porch off of the...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
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    2017 Rental Rate ~ $4200 per week, including the cleaning fee ~ Off-Season ~ $2000 per week, including the cleaning fee ~ Charming, antique, 5 BR home located on Chatham's 'loop', steps to the water and Stage Harbor Yacht Club. Enjoy the breathtaking views of Stage Harbor and Stage Harbor...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    3 Bedrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
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    2017 Rental Rate: In Season, $3175 per week, including the cleaning fee No Off-Season Weekly rentals from mid-JUNE to mid-SEPT Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home offers...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    2 Captains Row E Chatham Cape Cod1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a community pool & tennis court (Only 130 steps from your door!). Also offering Central AC, garage,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    • Balcony
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    Pet friendly
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    Smoking allowed
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    Take in panoramic views of the shimmering Atlantic from this 4-bedroom, 2-bath luxury house beside a beautiful wetlands conservation area. Built on Chatham's highest point, the house has incredible views, a touch of opulence, room enough for 8, and is just a 2 minutes from gorgeous ocean beaches...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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
    Welcome to Sea Glass! This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Warm water, sunsets, and miles of beach on Nantucket Sound awaits you just around the corner. This family friendly updated Cape Cod ranch has a large deck for outdoor entertaining...
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    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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