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Holiday Rentals in Chatham, MA

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    €6,677
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2015 Rental Rate: $1950 per week including the cleaning fee ~~ Off-Season: $1400 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL!!!! Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and sitting area with sofa bed as well as a... View all property information
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    €1,948
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2015 Rental Rate: $3375 per week including the cleaning fee ~~ Off-Season: $2275 per week including the cleaning fee Comfortable ranch located in the popular neighborhood of Hardings Shores. This beach house offers central air, wireless internet and upscale furniture and appliances. Enjoy the... View all property information
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2015 Rental Rate: $2275 per week including the cleaning fee Off Season: ~~ $1850 per week including the cleaning fee Spacious 3 bedroom with large yard on cul-de-sac, with deeded rights to Taylor's Pond! This wonderful summer home offers several living areas, a huge deck and more! You can easily... View all property information
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    €1,391
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    1 / 16
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2015 Rental Rates: $2400 including the cleaning fee. This a FRIDAY TO FRIDAY RENTAL. Off-Season: $1700 including the cleaning fee 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 short... View all property information
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    €2,597
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    1 / 10
    North Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2015 Rental Rate: In Season Rental Rate ~~ $3000 per week, plus a mandatory $200 cleaning fee~~~ Off Season Rate: ~~ $2800 per week, plus a mandatory $200 cleaning fee~~~ Beautiful neighborhood including 1300 ft. walk down private path to lovely, sandy ocean beach on Bassing Harbor. If you prefer... View all property information
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    €2,689
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    1 / 11
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    SUNDAY TO SUNDAY RENTAL 2015 Rental Rate: ~~ $3075 per week including the cleaning fee Classic beach house steps from the private beach of Harding Shores, where you can enjoy the views of Nantucket Sound from almost every room! Brand new living room couch and chair for the 2015 rental season!. The... View all property information
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    €5,564
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    1 / 10
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2015 Rental Rate: $8300 per week, including the cleaning fee~~ ~Off-season: $6300/wk including the cleaning fee Location is the name of the game for this sprawling Cape-style home in the Old Village. This lovely home is four doors down from Lighthouse Beach and 10 minute walk to Main Street. There... View all property information
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    €1,484
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    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2015 Rental Rate: $2450 per week including the cleaning fee ~~ Off Season: $1750 per week including the cleaning fee Charming year-round home, with central air conditioning, within walking distance to the warm waters of popular Ridgevale Beach! Recently updated, it is filled with new furnishings... View all property information
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    €1,090
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    About this property
    The Priscilla House is a lovely historic vacation home nestled on Main Street in the charming town of Chatham, Massachusetts on Cape Cod. Built by a sea captain for his daughter, Priscilla, this large vacation home sleeps 10-20+. Priscilla House is ideal for groups - family reunions, holidays, and... View all property information
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    €4,173
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    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    2015 Rental Rate: $8225 per week, including the cleaning fee Off-Season: $4725, including the cleaning fee Your Summertime memories begin in this lovely home overlooking Mill Pond and steps to the shops and restaurants on Main Street! Beautiful light and bright furnishings throughout and views from... View all property information
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    €2,782
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    1 / 11
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2015 Rental Rate: $4225 per week, including the cleaning fee ~~~Off Season $3225 per week, including the cleaning fee You will LOVE this beautiful home located in the Bailey's Path neighborhood, a lovely year round residential complex. The house is filled with gorgeous furnishings and upscale... View all property information
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    €2,782
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    About this property
    This 3 bedroom 3 full bath Chatham rental property is located down a quiet dirt road and has some views of Nantucket Sound. Forest Beach on Nantucket Sound is only 7/10ths of a mile away. This home boasts a finished basement with spare bedroom with a twin and futon, updated kitchen for the 2015... View all property information
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    €649
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    1 / 10
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    About this property
    Just Listed -- Immaculate Chatham Center Renovation. Walk to Beach & Village. $7500 Prime Summer Weekly Rate Your quintessential Chatham vacation awaits! This masterfully restored classic is situated in the heart of Chatham with the beach across the street and a 5 minute walk to town. The home... View all property information
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    €1,020
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    COMFORTABLE HOME WITH SO MUCH TO OFFER! Central air conditioning, cozy living room, sunny family room and dining room, wireless internet , flat screen television, deck with outdoor furniture and gas grill, nice private setting. Large patio and enclosed outdoor shower. Lovely home, nicely furnished... View all property information
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    €510
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    1 / 11
    North Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    About this property
    4550 per week to owner 3500 OFF SEASON 400 cleaning linen fee PETS ALLOWED WITH EXTRA DEPOSIT Additional amenities include: bedding rm1: king 1st floor master, a/c units: central, number of full and half baths: 4.5, shower only: 2, outdoor shower: enclosed, toaster/toaster oven, sleep cap: 11,... View all property information
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    €13,911
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    1 / 12
    6 Bedrooms, 8 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Cleaning $600 Checker $100 Linens $300 Additional amenities include: outdoor shower: enclosed, a/c units: central, toaster/toaster oven, number of full and half baths: 6 full 2 half, 1/2 bath: 2, bedding rm3: queen, priceclass: 10,000-15,000, lobster pot, distance to beach: within 2 blocks, open... View all property information
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    €487
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    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Paradise Found at this special retreat in this Cape Cod Vacation home Rental in Chatham called the Heron's Nest! This spacious , Four Bedroom, 3 bath luxury Chatham Rental will surely delight you in every way. Just a half mile to the warm waters and gentle waves of Ridgevale beach - this home is... View all property information
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    €2,736
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    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This 4 bedroom 2 full bath Chatham vacation rental is located just 1/10th of a mile from popular Ridgevale Beach. Amenities include washer/dryer, dishwasher, central A/C, cable TV (includes NESN) with DVD, WiFi, deck with furniture, gas grill, an outdoor enclosed shower and a new shed to store... View all property information
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    €1,067
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    About this property
    View Nantucket Sound from this 2 bedroom 1 bath traditional Cape cottage. Outside there is a charcoal grill and picnic table, while inside you'll find a microwave, a window a/c unit in the living room and cable TV (includes NESN). This property is only 1/10th of a mile from Ridgevale Beach. You can... View all property information
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    €1,206
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    1 / 10
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    About this property
    You'll be under 1/10th of a mile from Pleasant Street Beach at this cute two bedroom cottage. Amenities include cable TV (includes NESN, ESPN, Weather Channel, etc.) with DVD, WiFi, one window a/c unit in the living room, a deck with furniture and a gas grill, and an enclosed outdoor shower. This... View all property information
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    €533
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    1 / 18
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2015 Rental Rate: $6950 plus a mandatory $300 cleaning fee for one week, and $450 cleaning fee for a two week lease ~~June & September ~~ $5000/week, plus the cleaning Off-Season: $4000 per week, plus same cleaning fees as above. Fabulous renovated Cape located in the heart of Chatham with... View all property information
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    €3,431
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    1 / 11
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2015 Rental Rate: $3915 per week, JUNE THROUGH AUGUST 1, including the cleaning fee~ ~Mandatory $500 Security Deposit~ Adorable, nicely decorated 3 bedroom home located on the water's edge of White Pond. Stay cool with central air, and wake up and go for a swim from this very tranquil vacation... View all property information
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    €1,113
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2015 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1375 per week, including the cleaning fee Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an association picnic table and dock - great... View all property information
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    €417
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    1 / 34
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Take in views from almost every room at this updated Cape Cod Vacation Rental Home in Chatham. This home sits high on a hill overlooking both the Nantucket sound and the tidal marsh with its natural wildlife. Enjoy spacious outdoor decks with all around views of the ocean and it is a short walk to... View all property information
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Great views on Oyster River. Minutes to Hardings Beach. Two bedrooms on first floor and three upstairs. There is also a living area up on the second level with beautful relaxing views of boaters and swimmer enjoying beach time on Oyster Pond. Additional amenities include: single beds(2), bunks(3),... View all property information
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    €377
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    1 / 20
    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This Cape Cod Vacation home Rental in Chatham is just yards out the back yard to Forest Road Beach. Central A/C 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 crib with sheets & a bumper... View all property information
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    €3,246
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    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2015 Rental Rate ~ $5225 per week, including the cleaning fee ~~ Off-Season: $3725, including the cleaning fee~~ Gorgeous home located in a secluded yet convenient area of Chatham and overlooking Oyster Pond. The house is almost surrounded by waterviews! Open floor plan throughout with first floor... View all property information
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    €1,577
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Spend your summer vacation in this 3 bedroom 2 bath South Chatham vacation cottage. It is close to the beach and located in a quaint, beachy neighborhood. It has many convenient amenities such as central a/c, cable TV (includes NESN), WiFi, washer/dryer, dishwasher, enclosed outdoor shower, gas... View all property information
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    About this property
    Spend your Cape Cod vacation sunbathing by the pool at this 3 bedroom, 2 1/2 bath Chatham vacation rental home. This home is located at the end of a cul-de-sac within 3/10ths of a mile to Pleasant Street Beach and Forest Beach on Nantucket Sound. Amenities include a deck with deck furniture, a... View all property information
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    €1,252
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    About this property
    This South Chatham rental cottage has a newer kitchen with granite countertops and dishwasher, and an updated bathroom. Other amenties include 2 TV's with expanded cable (includes NESN), DVD,Wi-Fi, washer/dryer, enclosed outdoor shower, deck with furniture and gas grill. It is nicely appointed and... View all property information
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    €172
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    1 / 9
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This newly renovated house overlooks White Pond in Chatham and consists of 4 bedrooms and two full bathrooms. Located on the first floor is the master bedroom with king size bed, bathroom with washer/dryer, full kitchen, living room with cable television, enclosed sun porch, and screened porch. The... View all property information
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Location - Location-Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Whether you Enjoy cocktails on the traditional front porch, read a good book in the cozy sun room, eat outdoors on the mahogany deck or take in an outdoor shower - you... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
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    • Elder access
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    About this property
    2015 Rental Rate: $1950 per week, including the cleaning fee ~~ No Off-Season Great beach cottage, recently updated with new paint, new beds, and renovated bathrooms! Lovely new hardwood laminate flooring throughout! Located within walking distance to the kid-friendly warm waters of popular... View all property information
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    • Dishwasher
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Chatham, Newly Remodeled, One Mile to Main Street $2,850 PRIME SUMMER WEEKLY RATE This newly remodeled home is conveniently located under a mile from Chatham Village and set on a good sized lot in a quiet neighborhood. The home will be completed in early 2015. The home will have hardwood floors... View all property information
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    1 / 10
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    2014 Rental Rate: $7325 per week, including the cleaning fee 2015 Rental Rate $7325 per week including the cleaning Fabulous home with all the bells and whistles, with deeded access to Stage Harbor beach. Professionally decorated, this 4 bedroom home is full of new high-end furniture, fresh paint,... View all property information
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
    • Dishwasher
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    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    2015 Rental Rate: $4200 per week, including the cleaning fee ~~No Off-Season~~ Lovely home in the heart of Chatham Village! This beautiful home, filled with upscale furnishings, is a wonderful family rental in the perfect location. Walk out your front door and your are IN TOWN! Just steps to all... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    2015 Rental Rate: $3600 per week including the cleaning fee ~~ Off-Season: $2800 per week including the cleaning fee Spacious three bedroom home on Hall's Bluff, overlooking Nantucket Sound! This is a wonderful family rental - lots of space and just steps down a private path to popular Hardings... View all property information
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    On the Water! With Central Air and Wireless Internet-Pet Friendly too (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 the master... View all property information
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
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    • Elder access
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    About this property
    2015 Rental Rate $6425 with the cleaning included Off season $4425 per week with the cleaning included Entirely remodeled home, with new furniture and appliances throughout, located in the heart of Chatham! Walk to Chatham's downtown, or enjoy Chatham's famous band concert right around the corner.... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Dishwasher
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    • Internet Access
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    • Pets allowed
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    • Suitable for children
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    About this property
    JUST 1/10 OF A MILE TO TOWN!! Updated rental property that is just a short walk into town. Also a short walk to Oyster Pond beach area. Around the corner from Chatham Angler's ballgames, town playground, restaurants and shops! Nicely furnished, extremely comfortable interior, two bedrooms first... View all property information
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    €1,298
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Dryer
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    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    2015 Rental Rate: $1550 including cleaning fee ~~~~Off Season Rate: $1150, with cleaning fee Comfortable cottage located in the Harding Beach area. The perfect spot for your family's summer vacation! Relax on the screened in porch or take a quick walk down to Harding Beach! A great, affordable... View all property information
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    €4,544
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    5 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
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    • Internet Access
    • Satellite TV
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    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    2015 Rental Rate: $7540 per week including the cleaning fee ~~ Off Season Rate: $5240 per week including the cleaning fee $1500 Mandatory Security Deposit This Lovely antique home overlooking the Oyster Pond Harbor has just completed a fabulous renovation! The first floor has 2 open seating areas,... View all property information
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    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Dishwasher
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    • Pets allowed
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    • Suitable for children
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    • Elder access
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    About this property
    OWNER WILL ALLOW TENANTS TO BRING A DOG!! Charming antique home which is just a 5 minute walk to Stage Harbor. Just around the corner from Stage Harbor Marina and Yacht Club. Expansive farmers porch off the back and very large front yard. Owner offers use of tennis court next door from 10 AM to 5... View all property information
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    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Overview
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Great views of Nantucket Sound from this 3 bedroom 2.5 bathroom Chatham cottage. This is a brand new house with multiple furnished decks and balconies as well as a covered porch. You'll have all the amenities you'll need including washer/dryer, dishwasher, central a/c, multiple TVs with expanded... View all property information
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    €2,226
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    Overview
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    • ?
    About this property
    This lovely and bright South Chatham rental home is situated in a great neighborhood and only 3/10ths of a mile to Forest Beach on Nantucket Sound. There are four bedrooms with newer beds and two and a half baths, a family room upstairs and an open kitchen/dining area. Enjoy a barbeque on the... View all property information
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