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House Rentals in Chatham, MA

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 9
    North Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate $1575 per week with the cleaning included! No Off season FRIDAY TO FRIDAY rental 2016 Bright, cheerful home with a peek of Pleasant Bay from the back deck. Swimming in Pleasant Bay is nearby at Jackknife Beach! This charming year-round home is impeccably maintained and has a... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Enjoy in-town living. This bright two bedroom, two bath condo is a short walk to town, golfing, tennis, beaches and Chatham A's baseball games. This second level corner unit features a bright living room with eat-in dining room, kitchen and sliding doors to a walk-out balcony. The furnishings give... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    North Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    2016 Rental Rate: $5050 per week including linens and cleaning! ~~ Off-Season: $3900 per week including cleaning and linens Weekly rentals from mid-JUNE to mid-SEPT Gorgeous five bedroom home in secluded North Chatham neighborhood. This home features hardwood floors, WIFI and central air. Upscale... View all property information
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    North Chatham, Chatham 02650
    1 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    $7,800/week Peak Season (July 2 - September 2) $5,800/wk for the weeks of (6/25 and 9/3) $5,200/week Shoulder Season (6/18 and 9/10) $5,000/week Shoulder Season (6/11 and 9/17) $4,000/wk (before June 11 and after September 24) This beautiful newer 4 bedroom, 3 bathroom custom-built, Cape-style home... View all property information
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    Chatham, Cape Cod 02633
    1 / 23
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This beautiful, newer 4 bedroom, 3 bath custom home has an expansive deck and custom built patio area with plenty of outdoor seating, a fire pit and a gas grill. It is only 6/10ths of a mile to Forest Beach and even closer to a public tennis court and basketball hoop. The interior is open, bright... View all property information
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    Chatham, Cape Cod 02659
    1 / 29
    5 of 5 stars (2) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This 5 bedroom, 3 bath Chatham rental home has incredible water views of Taylor's Pond and is only 6/10ths of a mile to Cockle Cove beach by path. It is surrounded by oak trees creating a very private setting. There is a wonderful deck to lounge on, bbq on the gas grill or just take in the... View all property information
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    Chatham, Cape Cod 02659
    1 / 13
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $2275 per week including the cleaning fee Off Season: ~~ $1850 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious 3 bedroom with large yard on cul-de-sac, with deeded rights to Taylor's Pond! This wonderful summer home offers several living... View all property information
    Location Information
    South Chatham, Chatham 02659
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    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    You'll be only 5/10th's of a mile to popular Cockle Cove Beach at this 4 bedroom, 1.5 bathroom Chatham house. Amenities include washer, dryer, dishwasher, window a/c units in each bedroom and one in the living room, cable TV (includes sports and weather),DVD player, Wi-Fi, gas grill, deck with... View all property information
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    Chatham, Cape Cod 02659
    1 / 8
    North Chatham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2016 Rental Rate: $3225 per week, with the cleaning fee ~~Off-Season: $2225 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Spacious 5 bedroom on quiet cul-de-sac in prestigious North Chatham. Walk to beach, Band concerts, baseball games, Movies, and fish pier. House has... View all property information
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    North Chatham, Chatham 02650
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2016 Rental Rate: $3225 including the cleaning fee~~~ Off Season: $2225 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Private, traditional style cape house in the Sears Point area of Chatham. It has a lovely sun porch, a large living room and a large yard with lots of... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    OWNER VERY NEGOTIABLE... Additional amenities include: outdoor shower: enclosed, dist. to downtown: 2 miles, toaster/toaster oven, 1/2 bath: 1, square footage: 1800, lobster pot, area: west chatham, a/c units: 5- all br's & livingroom, outside furniture, allow pets, number of full and half baths:... View all property information
    Location Information
    Chatham, Cape Cod 02669
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $1650 per week, including the cleaning fee ~~No Off-Season~~ Light and bright ranch in Chatham's Countryside neighborhood. Hardwood floors throughout, on a nice quiet street. This charming ranch features central air and high speed internet! Located on a wooded lot, with a nice,... View all property information
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    Chatham, Cape Cod 02633
    1 / 29
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Tucked in the private Cannon Hill setting, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large 40 x 20 heated salt-water pool offers tons of comfort and is perfect for your summer getaway. Just a short 3 minute stroll away, on the calm waters of Pleasant Bay, a private... View all property information
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    Chatham, Cape Cod
    1 / 13
    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    2016 Rental Rate: $6300 per week, including the cleaning fee Off-Season:$4500 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely home in sought after Stage Neck area! This spacious home offers a private setting on just over an acre of land. It is about 2 miles from... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2016 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... View all property information
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    South Chatham, Chatham 02659
    1 / 6
    6 Bedrooms, 5 Bathrooms, Sleeps 13 | Quick View
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    Spend the summer on one of Chatham's most exclusive streets in this beautiful home. Located close to the beach, and to Main Street Chatham, the property at 61 Shore Road will please any discerning traveler. Graciously appointed with six bedroom and five full bathrooms, this home is well suited to... View all property information
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    Chatham, Cape Cod
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    393 STONY HILL ROAD CHATHAM Charming and completely renovated cottage, 7/10 of a mile to Scatteree Beach and the Cow Yard Landing and under 2 miles to Main St., Chatham for shopping, dining, and ice cream! This adorable one bedroom, air conditioned cottage has vaulted ceilings, exposed beams, a... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    122 CHATHAM CREST DRIVE Four bedroom three bath home located in a quiet part of Chatham. Two queen beds and 4 single beds this home sleeps 8. Outdoor shower, high speed internet, wifi and cable tv are some of the attributes of this vacation home. Three quarters of a mile from Ridgevale beach.... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Enjoy the convenient location of this 3 bedroom, 2 full bathroom classic Cape style Chatham rental home close to downtown Chatham, Oyster Pond, and Clafflin Landing. There is a spacious and private landscaped yard great for lawn games and barbeques. The kitchen has been updated with granite counter... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A very well maintained 3 bedroom, 2 bath cottage located just over 1/2 mile to Ridgevale Beach on Nantucket Sound. There is an open and spacious back yard that is great for games and bbq's. Amenties include central AC, washer, dryer, dishwasher, 2 TVs (includes sports and weather), 1 DVD player,... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Property ID: 107883 / Key #: 107883 / Property Name: 77 Bayview Road 2 bedroom, 1 bath home in South Chatham, sleeps 4. First bedroom has a double bed and second has 2 twins. WIFI and outdoor shower. $925 per week in season plus $60 handling fee & Either $55 vacation rental damage fee OR $500... View all property information
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    South Chatham, Chatham 02646
    1 / 9
    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    2016 Rental Rate: $4525 per week including the cleaning fee ~~ Off-Season: $3025 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT ~Experience a true Old Cape Cod vacation in this rambling home located about 2/10 of a mile from a private beach at Stage Harbor. Great views... View all property information
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    Chatham, Cape Cod 02633
    1 / 29
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Schoolhouse Pond just 1/10 mile! Charming custom remodeled Cape Cod home, 1/10 mile to Schoolhouse Pond Beach--perfect for freshwater beach lovers. First floor offers open kitchen / living area with AC unit and one first floor queen bedroom with a ceiling fan. Second floor has three bedrooms all... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    2016 Rental Rates: $5250 per week, including the cleaning fee FRIDAY TO FRIDAY Rental. ~~ Off-Season: $2750 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Gorgeous beach house on a quiet street just steps to Ridgevale Beach! "Beachy" decor and furnishings throughout!... View all property information
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    Chatham, Cape Cod 02633
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Waterfront / pond front with Private Access right from house to Schoolhouse Pond in Chatham. This home is located with fantastic access to a beautiful freshwater pond. It has gorgeous views from the deck and living area. It is also so convenient to Chatham Village, the best village on Cape Cod.... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    52 PLEASANT STREET NEW for 2015 SEASON CENTRAL a/c. Easy access to Pleasant Street Beach. The property has 3 bedrooms, two with 2 single beds and one with a queen size bed all on one level. Amenities include an enclosed porch, outside shower and WIFI. This property rents for $1700 per week in... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $2675 per week, including the cleaning fee Off-Season: $1925 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    OWNER'S SPECIAL - Book before July 4th and get $200 off weekly rate! Beautiful Chatham Get-away! Located on a sandy, dead end lane, this cottage is the perfect summer get-away. A large screened in porch fronts the cottage and is the perfect place for meals or evening game nights! Beautiful... View all property information
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    South Chatham, Chatham 02659
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Enjoy fantastic, unobstructed views of Red River Beach and Nantucket Sound from this 3 bedroom, 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. The property comfortably accommodates 8 people however can take up to 10 with the use of the full-size sleep... View all property information
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    Chatham, Cape Cod 02659
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    454 Training Field Road CHATHAM Lovely updated 3 bedroom home in close proximity to Pleasant Bay and Jackknife Cove beach. Just a few minutes drive to the quaint downtown village of Chatham. This home rents for $1600 per week in season. All rates plus $60 Handling Fee and $55 Vacation Damage... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $2175 per week, including the cleaning fee ~~Off-season: $1525/wk, including cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely updated cottage located in the popular Harding's Hills neighborhood. Spacious master bedroom with cathedral ceiling and private bath. The... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Cape cottage near wonderful Hardings beach Nice location about a third of a mile to popular, scenic Harding s beach. Typical knotty pine style cottage with central living room and enclosed rear porch open to the picnic patio. Has a small front deck too. Sleeps 6. $1500 per week plus $60 handling... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $2700 per week, with the cleaning fee~~~ Off-Season: $2200/wk, with the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great family rental located on a quiet street in the Ridgevale Beach area of Chatham. Not far from the beach, it offers a spacious back deck overlooking... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    196 Joshua Jethro Road This great new listing in Riverbay has been freshly rejuvenated with a new granite ktichen, hardwood floors, fresh baths and central a/c. This ranch has a master bedroom with a lovely ensuite bath with a new tile step-in shower. The other 2 bedrooms share a hall bath with... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    The location of this cottage is ideal ~ it's nestled off the main road between downtown Chatham and Andrew Hardings Beach. This is a quaint 2 bedroom 1.5 bath house. Close to fine restaurants, Chatham band concerts, ball games, the beach, the lighthouse and much, much more. Amenities include... View all property information
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    Chatham, Cape Cod 02633
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • Satellite TV
    • Patio
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rate: $1525 per week including the cleaning fee ~~ Off-Season: $925 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Light and bright two bedroom condo near Lighthouse Beach. New carpeting, new furniture, and new hardwood floors really brighten up the decor.... View all property information
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    Chatham, Cape Cod 02633
    1 / 40
    5 of 5 stars (1) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 2.5... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • DVD Player
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1375 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an... View all property information
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    Chatham, Cape Cod 02633
    1 / 7
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rate: $2800 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will love this 4 bedroom home near Ridgevale Beach! Located at the end of a dirt road with water views of a freshwater pond and... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy your Cape Cod vacation in this tastefully decorated, comfortable home. It is located in Hardings Beach Hills, only 4/10ths of a mile from Harding's Beach. There are 3 bedrooms, 2.5 bathrooms, a newer kitchen with granite countertops and stainless steel appliances as well as newer bathrooms.... View all property information
    Location Information
    Chatham, Cape Cod 02669
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    North Chatham
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2016 rental Rate: $7700 including the cleaning fee~~ Off-Season: $3850 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 located in the exclusive Cannon Hill Estates of North Chatham. This location... View all property information
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    North Chatham, Chatham 02650
    1 / 10
    6 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Porch
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the "loop" just around the bend from Stage Harbor. Wonderful area for walking and biking and a tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy yard is... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rate: $2175 per week, including the cleaning fee~~ Off-Season Rate: $1675 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Cozy saltbox located only a couple of blocks from Chatham's popular Harding's Beach. The first floor has a spacious bedroom with a... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    • DVD Player
    • Satellite TV
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rate: $2275 per week, including the cleaning fee Off-Season (June only): $1675/wk including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Located in a quiet neighborhood, 1/4 mile from Forest Beach. Charming home with a comfortable living room. Bright & spacious sun room... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Enjoy your vacation and be close to Nantucket Sound at this adorable 2 bedroom cottage only 3/10ths of a mile from Nantucket Sound beaches. This property has one portable AC unit in the Queen bedroom, washer, dryer, digital cable TV (includes sports and weather), DVD player, Wi-Fi, gas grill,... View all property information
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    Chatham, Cape Cod 02659
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rate: $1925 per week, including the cleaning fee *10 Day Special Aug 27-Sept 6 $1925!* ~~NO OFF SEASON~~ Wonderful, well-maintained home only a few minutes to Hardings Beach by car, without fighting Route 28 traffic; only 500 yards to the town landing on Oyster River (see photo on... View all property information
    Location Information
    Chatham, Cape Cod 02633