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Chatham House Rentals

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    Travellers to Chatham are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    431 Matching Rentals in ChathamView all 462 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    2017 rental Rate: $7850 including the cleaning fee~~***Owner Special Week of 7/8 Only: $6900 including cleaning, Call Now!!*** Off-Season: $3900 per week, including the cleaning fee ~ For 10 people only, lower level not available for Off-Season rentals~~ A large recently renovated 6 bedroom home...
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    North Chatham, Chatham 02650
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $1975 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning fee Enjoy the simple life in this classic, Chatham cottage. Located in the popular Hardings Hills neighborhood, a quick walk down to Hardings Beach! The newly enclosed porch overlooks the...
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    Chatham, Cape Cod 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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    • Private Outdoor Pool (Heated)
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    Experience "Chatham Coastal Charm". Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (.3). Sleeps 10! Peak Summer Weekly Rates:  last week of June until the first week in September: $5800-$7,000/week. Don't...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (6495)1 / 12
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    This rental property boasts both a main house and fully equipped cottage, great for extended family or friends. The main house has 3 bedrooms and 1 full bath. Amenities include central AC on the first floor and window AC units in the upstairs twin bedroom, washer, dryer, dishwasher, TVs with...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Come stay at: Donnadune. Pet Friendly! Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Peak Summer Weekly Rates:  last week of June until the first week in September: $4800 - $5,500/week Steps onto the large deck lead you to the entryway of this Cape home....
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    SUPER AFFORDABLE 2 BEDROOM 1 BATH COTTAGE IN CHATHAM1 / 17
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Price Range $1275-$1625 Rates include all charges; no hidden fees! NEW LISTING! Super affordable 2 bedroom/1 bath cottage! Walk to three Chatham beaches! Pet Friendly! This enchanting 2 bedroom/1 bath cottage sleeps 6 guests in a classic Cape within scenic walking distance to Scatteree Beach,...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    3 Bedrooms (King Master w/ Ensuite), 3 Bathrooms, Sleeps 8 - Sofa Sleeps 2 Addl Newly renovated (March 2016), quaint and charming in the heart of Chatham Village Center. Enjoy the full benefit of being steps away from the hustle and bustle of Main Street in one direction, or the scenic beaches and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    Short Drive to Everything! Our cape home offers lots of space for your family. 3/4 mile to Pleasant Bay Beach, 1 minute walk to Ryder’s Cove boat yard, few minutes walk to tennis courts and Cape Cod bike trail. 5 minutes drive to town center. Close to playground and baseball field - home of the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
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    Paradise Found at this special retreat in this Cape Cod Vacation home Rental in Chatham called the Heron's Nest! Peak Summer Weekly Rates:  last week of June until the first week in September: $4,450 - $4,600/week. This spacious , Four Bedroom, 3 bath luxury Chatham Rental will surely delight you...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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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, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Located in Chatham, this 4 bedroom 2 bath Cape Cod vacation rental home is only 0.3 miles to Ridgevale Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,800/week. This home has window AC units in the upstairs bedrooms as well as the 1st floor bedroom and...
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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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    This 3 bedroom cottage is the perfect location for your family stay in Chatham. The 3 bedrooms have one king room with a spacious en suite bathroom with Jacuzzi, and the other two with a queen sized bed in each. There are 2 sleeper sofas, one in the living room and the other in the family room. The...
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    Chatham, Cape Cod 02633
    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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    64 Waveland Chatham Lovely home in excellent condition located just a short drive to Hardings Beach. This home has been well cared for and features two separate living areas with DVD players, large flat-screen TV s and expanded cable for Red Sox games. The town landing on Oyster River is just...
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    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham Cape Cod Vacation Rental (4643)1 / 12
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    This adorable, updated and meticulously maintained 2 bedroom, 1 bathroom quintessential Chatham vacation cottage has views of Nantucket Sound. This rental is only 2/10ths of a mile to Forest Beach and Pleasant Street Beach. (The rental does not included access to the beach shown in the photos which...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, 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, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Lovely bright home with waterviews and central A/C in North Chatham ALSO AVAILABLE FOR HOLIDAY VACATIONS! Stunning, beautifully furnished home with central A/C and views of Pleasant Bay! Located in lovely North Chatham, this home is truly a special spot. The reverse floor plan maximizes views and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This rental is a comfortable 3 bedroom, 2 bath that sleeps 8. It sits on a pretty lot with a big backyard just 7/10th of a mile to Forest Beach in Chatham. A sunporch off the kitchen is great for that morning cup of coffee and the large deck has a gas grill for evening barbeques. The kitchen is...
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    South Chatham, Chatham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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.​ Peak Summer Weekly...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This recently renovated 4 bedroom, 2 bath house has a bright open floor plan with new furnishings throughout. This comfortable home is situated in a wonderful neighborhood with a great yard for children and is only 5/10ths of a mile from Nantucket Sound Beaches. A queen bedroom and a twin bedroom...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Whether you're settling in for a sun-filled beach vacation or seek a quiet seaside escape over the cooler months, this picturesque 3-bedroom, 2-bathroom home promises a charming and relaxing stay on the Cape year-round. Beautiful pine floors and old-world wood furnishings are set off by soft,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    ON THE WATER ...<BR><BR>* Beautiful water views! <BR>* Back decks open to mesmerizing views of Emery Pond <BR>* Hammock and patio furniture chosen for comfort and relaxation!<BR>* Direct access to pond from backyard. <BR><BR>* Clean swimmable pond.<BR>* Bass fishing plentiful!<BR>* Gas grill.<BR>*...
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    Chatham, Cape Cod 02633
    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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    About this property
    Enjoy a timeless beach vacation in this lovely Chatham home, 3-bed 2-bath, set near the beach with beautiful private gardens. Here, you’re only a mile from the beach, close to biking trails, and surrounded by fishing opportunities. Not to mention the shops and restaurants on Main Street! There’s a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Patio
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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 close to the water and close to Main Street. Walk to town on sidewalks and enjoy the amazing shops and restaurants. Walk to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This adorable 3 bedroom 1.5 bathroom Chatham vacation cottage has views of the Cockle Cove salt marsh and is just steps to Cockle Cove beach on Nantucket Sound. Amenities include two window AC units (one in the living room and one in the bunk bed room), cable TV (includes sports and...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Panoramic views of Nantucket Sound from this traditional 4 bedroom, 2 full bath Cape beach house with direct access to a private beach. Living space abounds on the first floor with multiple sitting areas, large dining area and furnished deck. A master bedroom with queen bed is also located on the...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Come Stay at: Good Times! Welcome to your Beach House! This Cape Cod Vacation rental home is located in Chatham in the Harding's Beach Hills (just .3 mile to Harding's Beach and .2 mile to The Buck's Creek Association dock and picnic area). Peak Summer Weekly Rates:  last week of June until the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Come Stay at: Chatterbox! Location! Location! Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,000 - $4,200/week. Whether you enjoy cocktails on the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Enjoy staying in the heart of Chatham Village in this new, tastefully appointed 2 bedroom, 2.5 bath 1,300 sq. ft. home. Downtown Chatham is just steps away where you can enjoy shopping, fine restaurants, band concerts, ball games and much, much more. This home is only 2/10th's of a mile to Oyster...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    About this property
    This peaceful 3BR, 2BA woodland Chatham home (sleeps 6) is located right on the Monomoy River. Patio doors open to the travertine stone terrace, where a hot tub overlooks the water. Large windows, cathedral ceilings, soft colors, and modern conveniences make this home oh-so-inviting. INSIDE THE...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 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 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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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh water ponds and just a short drive to Pleasant Bay! The property offers four comfortable bedrooms and two baths, sleeping up to 8. The first floor has a fully equipped kitchen, cozy...
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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 6 Quick View
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    2017 Rental Rate: $2675 per week, with the cleaning fee ~~September: $1925 per week, including the cleaning fee~~ Take advantage of the quick walk to the Chatham A's Ball Field, the playground and Main Street from this pristine three bedroom ranch! There are two living spaces, great for the kids...
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    Chatham, Cape Cod 02633
    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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    About this property
    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Welcome to #25 Stones Throw. This sunny end unit has everything you need for a relaxing vacation. There is a pool in the complex. There are no less that four beaches within a five minute drive. Salty's market is just down the hill, past the Truro Winery - also a great place for wine tasting. If...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    South Chatham Cape Cod Vacation Rental (8975)1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    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. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2000-$2,600 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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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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! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,000/week. Get away to this 1 bedroom cozy cottage located right at the beach in Chatham, the best of Cape Cod-Sleeps 4. Perfect for...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    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!! Peak Summer Weekly Rates:  last week of June until the first week in September: $9,100 - $9,400/week Whether you are soaking in the hot tub on...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, 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, 4 Bathrooms, Sleeps 10
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    Chatham Cape Cod Waterfront Vacation Rental (10325)1 / 42
    (2)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    A traditional Cape Cod pond-front compound set on a beautifully landscaped 2-acre lot with lovely views of Black Pond. Enjoy summer breezes while relaxing on one of the many patios in this very private yard perfect for lawn games, barbeques or simply stargazing. The main home has 4 bedrooms and 3.5...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    2017 Rental Rate: $1650 per week, including the cleaning fee~~No Off-Season Updated and light two bedroom home, on Hitching Post Rd near the ball field and the playground! Great yard for kids to play while you enjoy spending time in the sunroom! It is a short walk to the Rotary at the beginning of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This recently updated 4 bedroom, 2 bathroom home is located in the desirable Stage Harbor area of Chatham. On the ?loop,' this home is just a short walk to Battlefield Landing on Stage Harbor and only 1 mile to the shops and restaurants in downtown Chatham or to the warm waters of Oyster Pond. This...
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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 6 Quick View
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    Kid friendly
    Smoking allowed
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    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,400-$3,975/week. 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2016 Rental Rate: $1050 per week, including the cleaning fee ~~Off Season: $750/wk, with cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Quaint 2 bedroom cottage surrounded by beautiful gardens! Sitting on .5 acre in lovely North Chatham, this private getaway is just what the doctor ordered....
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    Chatham, Cape Cod 02650
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chatham  Cape Cod Waterfront Vacation Rental (6520)1 / 22
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Beautiful water views of Pleasant Bay from this charming, sprawling ranch which has 4 bedrooms and 3 baths. There is a spacious living room, dining room, large deck, all with spectacular views overlooking Pleasant Bay. Amenities include AC (central throughout + wall unit in master queen), washer,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This is a terrific, newer, bright 3 bedroom, 2 full bathroom Chatham rental home situated only 2/10ths of a mile from popular Ridgevale Beach. This home is nicely decorated with newer, tasteful furnishings. Amenities include central AC, washer, dryer, dishwasher, cable TV (includes sports and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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