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Holiday 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.
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    From
    €2,457
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    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    €625
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    4 Bedrooms / 3 Bathrooms / Sleeps 6
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    €1,072
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    €3,127
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    1 / 12
    4 Bedrooms / 5 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Pets allowed
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    About this property
    2015 Rental Rate: $5000 per week, including the cleaning fee Off-Season $3750 per week, with the cleaning fee Beautiful North Chatham home with peeks of Crows Pond and three decks! This year-round home is filled with upscale furnishings and decor. It offers two large separate living spaces, a... View all property information
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    €1,340
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    1 / 10
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    2015 Rental Rate: $2350 per week, including the cleaning fee ~~Off-Season: $1650/week, including the cleaning fee. Light and bright cottage just steps to the warm Nantucket Sound waters of Pleasant Street Beach! Tasteful, traditional furnishings throughout. New appliances and stone counters in... View all property information
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    €3,440
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    1 / 17
    North Chatham
    5 Bedrooms / 5 Bathrooms / Sleeps 11
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    • Dryer
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    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
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    • Suitable for children
    • ?
    • x
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    About this property
    2015 Rental Rate: $4950 per week including linens and cleaning! ~~ Off-Season: $4250 per week including cleaning and linens Gorgeous new home in secluded North Chatham neighborhood. This home features hardwood floors, WIFI and central air. Lots of games, puzzles, sports and beach gear for the kids.... View all property information
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    €331
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
    • Dishwasher
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    • Washer
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Swim, fish, bike or just plain relax at this private,comfortable retreat in Chatham. In a quiet, wooded setting, cooled by the breezes from the pond,and ceiling fans, the home's open floor plan is well suited for gathering. The first floor of this home includes the living room, dining room, well... View all property information
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    €1,206
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    1 / 8
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate ~~ $1500 per week, with the cleaning fee ~ Off-Season is the same rate ~ OFF Season is negotiable Enjoy everything Chatham has to offer from this perfect, small home centrally located to beaches and downtown. Light and bright furnishings. A fantastic deck in the back of the home... View all property information
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    €536
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    1 / 11
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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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
    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: Pre-season (May 23-June20) $1,200 per week ~~~IN SEASON: $1800 per week (June 20-Sept 12) ~~~Post-season (Sept 12-Oct 17th) $1,200 per week Off-season (subject to Owner's prior approval) $600 week $175 MANDATORY cleaning fee per lease Light and airy - hardwood floors, lots of... View all property information
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    €1,206
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    1 / 10
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
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    About this property
    PERFECT GETAWAY THAT IS SO CLOSE TO THE BEACH AND PET FRIENDLY!!! This cozy, comfortable beach cottage is located in the Horne Cottage area and is a five minute walk to beautiful beach just south of Lighthouse Beach near Outermost Marina. Lighthouse Beach is also about a 10 minute walk from this... View all property information
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    €603
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    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Dryer
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    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    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). Don't miss this 'fan favorite' Cape Cod Vacation Rental home in Chatham with heated pool that is very close to Hardings Beach (.3 Chatham's most popular... View all property information
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    €2,323
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    1 / 14
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Spend your beach vacation in this 3 bedroom 3 bath Chatham home on Mill Creek in a pleasant neighborhood. This Chatham rental overlooks Mill Creek and has views of Nantucket Sound. You can launch a kayak to paddle into Nantucket Sound right from the deck on the property. It's only 5/10th's of a... View all property information
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    €2,144
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    1 / 14
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    WALK TO TOWN LOCATION!! Spectacular rental property located just a short walk to restaurants, shops, Chatham Bars Inn, Seaside Links 9 Hole Golf Course, Chatham Angler's Ballfield, town playground and Oyster Pond beach area. This immaculate rental has so much to offer....four bedrooms/2.5 baths,... View all property information
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    €382
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    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • ?
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    About this property
    Classic North Chatham Escape, Pet Friendly $3,300 PRIME SUMMER WEEKLY RATE This home has 4 bedrooms and classic Cape Cod decor. All of the modern amenities are included: AC units in all bedrooms, WiFi, flat screen TV with digital cable, washer/dryer, and a completely updated kitchen with granite... View all property information
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    €737
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    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: $1225 per week including the cleaning fee ~~ Off-Season: $950 per week including the cleaning fee Adorable one bedroom unit just steps to Lighthouse Beach! A quick walk to downtown Chatham for dinner, shopping and more, this charming condo is perfect for a two people, but there is... View all property information
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    €983
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    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: $1725 per week including the cleaning fee ~~ Off-Season: $1225 per week including the cleaning fee Charming three bedroom cottage located at end of dead end street near Cockle Cove Beach. Quiet setting and you can enjoy the cozy deck overlooking the salt marsh. Ride bikes down to... View all property information
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    €849
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    1 / 11
    South Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Grill
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    UPDATED HOME THAT HAS DEEDED RIGHTS TO TAYLORS POND. Short drive to Nantucket Sound beaches. Tastefully furnished ranch style home with wireless internet, 3 bedrooms, 2 baths, hardwood floors, open floor plan, nice kitchen! Nice deck to enjoy outdoor dining and relaxing after a day at the beach,... View all property information
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    €715
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    1 / 7
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: $1500 per week, including the cleaning fee~~~NO OFF-SEASON~~~ Enjoy your Chatham summer vacation in this light and bright pet-friendly home on a quiet side street, on the way to Ridgevale Beach, one of Chatham's most popular family beaches! Filled with bright colors and comfy... View all property information
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    €2,502
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Dryer
    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • x
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    • Wheelchair access
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    About this property
    You'll have fantastic views of Nantucket Sound from this 3 bedroom 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. It offers a washer/dryer, dishwasher, a gas grill, central air conditioning, WiFi, and cable TV (includes NESN) with DVD. There is a... View all property information
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    €2,859
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    1 / 29
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Dryer
    • Grill
    • 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
    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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    €1,429
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    1 / 11
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: $2800 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee 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 surrounded by conservation land, it is quiet and... View all property information
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    €1,787
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
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    About this property
    Enjoy your summer vacation in this charming bright contemporary home just 5/10ths of a mile to Pleasant Street and Red River Beaches. This 3 bedroom, 2 bath home was fully renovated in 2007 including bathrooms, kitchen and flooring. Enjoy furnished multi-level decks with a gas grill, nice yard and... View all property information
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    €737
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    1 / 5
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    2015 Rental Rate: $1800 per week, including the cleaning fee ----Off Season: $975 per week, including the cleaning fee Cute 3 bedroom ranch, walking distance to town and Oyster Pond. A great new 2nd family room just finished in the lower level! No deck, but there is a picnic table in the backyard.... View all property information
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    €1,340
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    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    2015 Rental Rate: $2375 per week including the cleaning fee ~~ Off-Season: $1675 per week including the cleaning fee Updated rental close to downtown Chatham and all it has to offer! Central Air Conditioning throughout! Walk down to the Chatham Playground or Chatham's A's baseball games too.... View all property information
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    €893
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • Suitable for children
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    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 A/C unit in the bedroom with Queen, washer/dryer, digital cable TV (includes NESN, ESPN, etc..) with DVD, WiFi, gas grill,... View all property information
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    €1,206
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    1 / 13
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Satellite TV
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    About this property
    ID #PATT41 Chatham Vacation home, only 0.1 miles to Ridgevale Beach which is next to Cockle Cove Beach on Nantucket Sound, with beach access from Bucks Creek Bridge from Nantucket Drive. [~]Catch views of Buck Creek and the Ocean beyond from the living room of this vacation cottage that has a... View all property information
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    €849
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Satellite TV
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    • Smoking allowed
    • Suitable for children
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    • x
    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: $1325 per week, including the cleaning fee ~~~ Off-Season: $1075 per week, including the cleaning fee Charming cottage in the woods and only 2 minutes to Oyster River Public Boat Landing. Small screened-in porch attached. A great vacation cottage for a small family. Each bedroom... View all property information
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    €1,787
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    1 / 8
    North Chatham
    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    2015 Rental Rate: $3225 per week, with the cleaning fee ~~Off-Season: $2225 per week, with the cleaning fee~~ 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 just been completely renovated with... View all property information
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    €3,350
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    1 / 20
    5 Bedrooms / 5 Bathrooms / Sleeps 11
    Overview Make Enquiry
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    • Air Conditioning
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    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
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    About this property
    2015 Rental Rate ~~ $5325 per week including cleaning Off Season $4,075 per week included cleaning Gorgeous, newer home located just a quick walk to Hardings Beach. All the upscale furnishings throughout this home are brand new for the 2012 season! Plenty of bedrooms for a large group, including a... View all property information
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    €5,092
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    1 / 13
    5 Bedrooms / 5 Bathrooms / Sleeps 11
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    • Air Conditioning
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    • Grill
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    • Satellite TV
    • Washer
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    2015 Rental Rate: $6000 per week, including the cleaning fee 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 downtown Chatham, and a walk to Oyster River landing for kayaking. Built on three levels, it... View all property information
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    North Chatham
    3 Bedrooms / 3 Bathrooms / Sleeps 9
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 mile to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 2 miles to Main St., Chatham for shopping,... View all property information
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    €3,127
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    1 / 12
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • Suitable for children
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    About this property
    Lovely renovated home with central air just steps away from Lighthouse Beach. Lovely renovated home just 5 doors down from beautiful Lighthouse Beach- you don t have to worry about parking! This home features many upgrades including central air conditioning and lovely, comfortable living spaces. So... View all property information
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    €715
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Dishwasher
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    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
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    About this property
    2015 Rental Rate: $1525 per week including the cleaning fee ~~ Off-Season: $925 per week including the cleaning fee Light and bright two bedroom condo near Lighthouse Beach. New carpeting, new furniture, and new hardwood floors really brighten up the decor. Many updates in 2013, including new... View all property information
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    €1,206
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    SHORT DRIVE TO THE BEACH AND AROUND THE CORNER TO THE BIKE PATH!! This immaculate 4 bedroom, 2 bath home was completely renovated in 2010, with central air conditioning, master bedroom suite with private bath, wireless internet, washer/dryer, fully equipped kitchen with dishwasher, sunny dining... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    About this property
    $3,800/week Peak Season (July 18 - August 28) $3,300/week Shoulder Season (June 27 - July 17) $3,300/week Shoulder Season (August 29 - September 4) $2,400/week Off Season (anything prior to June 27 and anything after September 5) This beautiful newer home is located in Hardings Beach Hills 5/10ths... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Satellite TV
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    • Smoking allowed
    • Suitable for children
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    About this property
    Located in Chatham, this 4 bedroom 2 bath Cape Cod vacation rental home has window A/C units in the upstairs bedrooms as well as the 1st floor bedroom and living area to keep you cool and offers WiFi to keep you connected. .3 miles to Ridgevale Beach. Through the side door off of the driveway,... View all property information
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    South Chatham
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Suitable for children
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    About this property
    This gorgeous sprawling home on 3 acres is surrounded by 50 acres of conservation land. It is extremely private, very quiet, has its own pond, and plenty of space for sunbathing and outside play, large, expansive decks, lots of room for entertainment inside and out. It is completely equipped with... View all property information
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    South Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    This ranch style Cape Cod Vacation Rental home in Chatham has undergone a complete refresh with all new --paint, new bathroom, kitchen, flooring, furniture and landscaping. A/C units in the bedrooms on the main floor and wifi too.​ This home is South of Route 28 and you have your choice of Pleasant... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    2015 Rental Rate: $2175 per week, including the cleaning fee ~~Off-season: $1475/wk, including cleaning fee Lovely updated cottage located in the popular Harding's Hills neighborhood. Spacious master bedroom with cathedral ceiling and private bath. The kitchen is also updated, light and open. There... View all property information
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    €7,147
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • Satellite TV
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    • Waterfront
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    About this property
    2015 Rental Rate ~~ FRIDAY TO FRIDAY: $12,550 per week, including the linens and cleaning fee Off season $8550 per week including the cleaning and linens This one of a kind secluded residence overlooking a stunning Chatham Seascape exudes timeless elegance and charm. Set within a spectacular... View all property information
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    €625
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    4 Bedrooms / 4 Bathrooms / Sleeps 11
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    • Air Conditioning
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    • Satellite TV
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    • Water Views
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    • Pets allowed
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    • Suitable for children
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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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    €2,234
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • x
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    About this property
    Spend your vacation in this newer 2+ bedroom 2.5 bath Chatham rental home situated on a lovely country lane 3/10ths of a mile to Pleasant Street beach on Nantucket Sound. This home boasts nearly every possible amenity including central air, washer/dryer, dishwasher, cable TV (includes NESN) with... View all property information
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    €2,144
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    You'll have everything you need at this 4 bedroom 3 bathroom Chatham rental home less than a mile from Chatham Village. It has nearly every amenity including washer/dryer, dishwasher, central a/c, cable TV's (includes NESN) with DVD players, Wi-Fi, a ping pong table, deck with furniture, an outdoor... View all property information
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    €1,385
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Suitable for children
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    About this property
    This 3 bedroom 1 bath cottage is across from (and has deeded rights to) fresh water Emery Pond. It's a good spot to put in a kayak or canoe. There's a nicely, manicured back yard with furnished deck and charcoal grill. Amenities include a 'Smart' TV with NetFlix access, WiFi, window a/c units (one... View all property information
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    €1,340
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Air Conditioning
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    • Satellite TV
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    • Smoking allowed
    • Suitable for children
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    About this property
    255 Tanglewood Drive CHATHAM This Chatham home is conveniently located within a short drive to many salt water beaches and fresh water ponds. The Chatham Bike Path is less than 1 mile away. Home is also convenient to down town Chatham and Harwich Port offering many shopping and restaurant choices.... View all property information
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    €290
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
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    • Satellite TV
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    • Pets allowed
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    • Suitable for children
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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... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    DEEDED PATH THAT LEADS RIGHT TO BEACH JUST SOUTH OF LIGHTHOUSE BEACH AREA! The property is also about a 1/2 mile to beautiful Lighthouse Beach. Great neighborhood for those that love walking to the beach! Just come and go without having to pile in the car. Three portable air conditioning units in... View all property information
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    €4,690
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    4 Bedrooms / 5 Bathrooms / Sleeps 11
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    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    2015 Rental Rate: $7300, including the cleaning fee This is a FRIDAY TO FRIDAY RENTAL Off Season: $5550 per week, including the cleaning fee $1500 Refundable Security Deposit Required Gorgeous, upscale home located in the heart of Chatham, close to Main St and Shore Rd. Nice, private back yard and... View all property information
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    €2,859
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Satellite TV
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Classic old-style Cape Cod home overlooking Chatham Harbor with private stairs leading down to Lighthouse Beach. SUNDAY arrival and departure this Classic old-style Cape Cod living in a simply spectacular location. This 4 bedroom home inside the Old Village Historic District overlooks gorgeous... View all property information
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    €893
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    IMMACULATE THREE BEDROOM/TWO BATH CAPE THAT IS A SHORT WALK TO TOWN! Just about 7/10's of a mile to Chatham Angler's ballfield!! Cozy fireplaced living room, updated kitchen and family room are perfect for up to six people. Property has window air conditioning units in the bedrooms, wireless... View all property information
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