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Vacation Rentals in Chatham, MA

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    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 17
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 29
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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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    Chatham, Cape Cod 02659
    1 / 26
    North Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Completely renovated condo in North Chatham. Enjoy this lovely condo with all amenities including Central A/C mini split, wifi, and new furnishings. Sleeps 4. Peak Summer Weekly Rates:last week of June until the first week in September: $1,275/week. Conveniently located in a very quiet area of... View all property information
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    North Chatham, Chatham 02650
    1 / 27
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This newer 3 bedroom, 2 bath Chatham vacation home, located in a quaint neighborhood on a private street, has water views of Nantucket Sound and Red River Beach as well as conservation area. It is only 200 yards to the small, semi-private Association beach and a short distance to Pleasant Street... View all property information
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    Chatham, Cape Cod 02659
    1 / 24
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Enjoy your Cape Cod vacation in this updated, bright and airy 5 bedroom, 3 bath Chatham rental property. This home is located in a lovely setting, with a terrific deck overlooking a saltmarsh and just 4/10ths of a mile from popular Ridgevale Beach. Multiple spacious living areas with many windows... View all property information
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    Chatham, Cape Cod 02633
    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 / 11
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This Chatham rental home has 3 bedrooms and 1.5 baths. It's situated in a private setting, abutting conservation and convenient to both downtown Chatham and beaches. This property is only 1/2 mile to White Pond, a large fresh water pond which is great for fishing, swimming or paddle boarding.... View all property information
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    Chatham, Cape Cod 02633
    1 / 18
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This recently renovated 4 bedroom, 2 bath house has a bright open floor plan with new furnishings throughout. This comfortable home is situated in a wonderful neighborhood with a great yard for children and is only 5/10ths of a mile from Nantucket Sound Beaches. A queen bedroom and a twin bedroom... View all property information
    Location Information
    Chatham, Cape Cod 02659
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    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    RENOVATED very bright, beachy condo, 2bdrms/2bths. This unit comes equipped with AC, fully stocked kitchen and 2 decks to enjoy your wine/coffee. The decks overlook Little Mill Pound. This condo is located in town and the famed, kid friendly Oyster Beach & Lighthouse Beach are a 10 minute... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beautiful views of Nantucket Sound abound from this 2 bedroom, 1.5 bath traditional Chatham vacation rental only 4/10ths of a mile to Red River Beach and 6/10ths of a mile to Pleasant Street Beach. There is a sun room off the living room with a full-size sleep sofa and the full bath was recently... View all property information
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    Chatham, Cape Cod 02659
    1 / 27
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spend your Chatham vacation in this beautiful 4 bedroom, 2.5 bath home located 500 feet from Pleasant Street Beach. This is a truly unique, custom home featuring gorgeous woodwork throughout, a first floor master bedroom with Jacuzzi tub, a bright and beautiful kitchen with granite and silestone... View all property information
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    Chatham, Cape Cod 02659
    1 / 14
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    This 3 bedroom 1 bath rental is located within walking distance to two fresh water ponds and is just a mile from downtown Chatham. Emery Pond is perfect for kayaking while the much larger White Pond is great for swimming and paddleboarding. The bike path is also adjacent to the neighborhood making... View all property information
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    Chatham, Cape Cod 02633
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Patio
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    About this property
    16 ELLIS Pet friendly home in Chatham sleeps 4. Two bedrooms one with a queen and bedroom two has a queen and a single bed. Outdoor seating on the deck is spacious. Enclosed outside shower. One and a half baths. WiFi. A/C in the bedrooms. A short drive to Harding beach. FRIDAY arrival and... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 16
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    About this property
    64 Waveland Chatham Lovely home in excellent condition located just a short drive to Hardings Beach. This home has been well cared for and features two separate living areas with DVD players, large flat-screen TV s and expanded cable for Red Sox games. The town landing on Oyster River is just... View all property information
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    West Chatham, Chatham 02669
    1 / 8
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Come stay in this lovely, light, bright and open 2+ bedroom, 2.5 bath home with newly installed wall mounted AC unit on the first floor and window units in each bedroom. The deck overlooks a very private backyard with enclosed outdoor shower and charcoal grill. This rental is convenient to... 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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    04/01/17 - 06/24/17 $1,700 06/24/17 - 07/01/17 $2,100 07/01/17 - 08/26/17 $2,900 08/26/17 - 09/02/17 $2,000 09/02/17 - 10/28/17 $1,700 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 24
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Enjoy your vacation in this well maintained, bright, contemporary 4 bedroom, 2.5 bathroom Chatham rental home situated in a lovely neighborhood located along the popular Chatham 'Loop' and only 1/10th of a mile to Stage Harbor town landing where you can stroll along the water's edge, kayak, paddle... View all property information
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    Chatham, Cape Cod 02633
    1 / 25
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This recently updated 4 bedroom, 2 bathroom home is located in the desirable Stage Harbor area of Chatham. On the ?loop,' this home is just a short walk to Battlefield Landing on Stage Harbor and only 1 mile to the shops and restaurants in downtown Chatham or to the warm waters of Oyster Pond. This... View all property information
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    Chatham, Cape Cod 02633
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    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This 4 bedroom, 2.5 bathroom house is within walking distance to downtown Chatham with some of the best restaurants and shopping that Cape Cod has to offer. The living room offers plenty of new, comfortable seating and the kitchen, with granite countertops and stainless appliances, is fully stocked... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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 only 3/10ths of a mile to Pleasant Street Beach on Nantucket Sound. The master bedroom with queen bed is located on the first floor. The second floor bedroom has a queen and a twin bed and... View all property information
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    Chatham, Cape Cod 02659
    1 / 23
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 both gas and charcoal grills. It is only 6/10ths of a mile to Forest Beach and even closer to a public tennis court and basketball hoop. The interior... View all property information
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    Chatham, Cape Cod 02659
    1 / 22
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There is a sunken dining room off the main living room that opens to a furnished patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath, wet-bar area, two sleep-sofas... View all property information
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    South Chatham, Chatham 02695
    1 / 12
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Enjoy this classic 3 bedroom, 1 full bath Cape beach cottage only 3/10ths of a mile to popular Ridgevale Beach. Amenities include washer, dryer, dishwasher, two window AC units (one in the Queen bedroom and one in the bedroom with 2 Twins), cable TV (includes sports and weather), DVD player, Wi-Fi,... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy your vacation in this bright, open 3+ bedroom, 2 bath Chatham home on a cul-de-sac in a pleasant neighborhood. This home is only one-half mile to Cockle Cove Beach or 2/10th's of a mile to Taylor's Pond where you can launch a kayak to paddle into Nantucket Sound. New furnishings include a... View all property information
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    Chatham, Cape Cod 02659
    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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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    Chatham, Cape Cod 02659
    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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    Chatham, Cape Cod 02633
    1 / 47
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    ON THE WATER ...<BR><BR>* Beautiful water views! <BR>* Back decks open to mesmerizing views of Emery Pond <BR>* Hammock and patio furniture chosen for comfort and relaxation!<BR>* Direct access to pond from backyard. <BR><BR>* Clean swimmable pond.<BR>* Bass fishing plentiful!<BR>* Gas grill.<BR>*... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stay in the heart of Chatham Village in this well-maintained 3 bedroom 1.5 bathroom home. Situated in a quiet neighborhood only 4/10ths of a mile from the shops and restaurants on Main Street, baseball field, playground and the Fish Pier. This traditional Cape home features a queen bedroom on the... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This 3 bedroom, 3.5 bath home is situated at the end of a cul-de-sac and only 8/10ths of a mile to popular Ridgevale Beach. The spacious master bedroom with queen bed is on the first floor while the other 2 bedrooms and full bathroom are on the 2nd floor. The finished lower level has a sitting area... View all property information
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    Chatham, Cape Cod 02659
    1 / 18
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy your Chatham vacation in this well appointed, light and bright, updated 4 bedroom, 3 1/2 bath, water-front home with breathtaking views of Pleasant Bay, North Beach and the Atlantic beyond. The comfortably furnished patio overlooks a small cove in Pleasant Bay were you can easily launch your... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    A very well maintained 3 bedroom, 2 bath home 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), DVD players, Wi-Fi,... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Charming 3 bedroom, 1 bath cottage with views of Nantucket Sound from the rooftop deck. There is a good sized backyard and Forest Beach is just 3/10ths of mile away. Amenities include a window AC unit in each bedroom, cable TV (with basic cable only; no NESN, ESPN, Weather Channel, etc.) with a DVD... View all property information
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    South Chatham, Chatham 02659
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Enjoy your summer vacation in this charming 3+ bedroom 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches. Situated just 2/10ths of a mile to Mill Creek which is great for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include washer, dryer, dishwasher,... View all property information
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    Chatham, Cape Cod 02659
    1 / 38
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    ​Pet Friendly! Updated 4 Bedroom home sleeps 10-walk to Harding's Beach with Deck-Outdoor shower- A/C units. Wifi too. Peak Summer Weekly Rates:(last week of June until the first week in September) $2,600 Walk to Harding's Beach from this Cape Style home! Enter into the open dining room with... View all property information
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    West Chatham, Chatham 02669
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    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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    Chatham, Cape Cod 02659
    1 / 15
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Less than a mile from Chatham Village this 4 bedroom, 3 bathroom rental home has all the comforts of home. The master bedroom with queen bed and a second bedroom with 2 twins are located on the 1st floor. The other two bedrooms and a bathroom are located on the second floor. Amenities include... View all property information
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    Chatham, Cape Cod 02633
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:last week of June until the first week in September:$2,000/week. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket Sound) in Chatham's Old Village and a few blocks... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    North Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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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    North Chatham, Chatham 02650
    1 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Panoramic views of Nantucket Sound from this traditional 4 bedroom, 2 full bath Cape beach house with direct access to a private beach. Living space abounds on the first floor with multiple sitting areas, large dining area and furnished deck. A master bedroom with queen bed is also located on the... View all property information
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    Chatham, Cape Cod 02659
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    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rates: $2600 including the cleaning fee. Off-Season: $1700 including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Wonderful, light and bright summer home located just steps from Taylor's Pond, the Eel River and the warm waters of the Nantucket Sound. Even better, there is a... View all property information
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    South Chatham, Chatham 02659
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This 3 bedroom, 2 bath house is in a quiet neighborhood abutting a wooded backyard. You'll be 7/10ths of a mile from Pleasant Street Beach and just a smidge further to Red River Beach. Amenities include window AC units in all three bedrooms, washer, dryer, dishwasher, Wi-Fi, cable TV (includes... View all property information
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    Chatham, Cape Cod 02659
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    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Pet Friendly! Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Peak Summer Weekly Rates:last week of June until the first week in September: $5,200 - $5,500/week Steps onto the large deck lead you to the entryway of this Cape home. Welcome back in time to... View all property information
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    North Chatham, Chatham 02650
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    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    0.1 mile from a popular summer Nantucket Sound beach… can walk or ride or /access to private beach via path along marsh just steps away from the house quiet family area… ranch / cottage style house with summer beach flavor with views of Taylor Pond 1 bathroom / eat in kitchen / deck / Weber gas... View all property information
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    South Chatham, Chatham 02659
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Enjoy your summer vacation in this charming 3 bedroom, 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches and just 2/10ths of a mile to Mill Creek which is great for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include central AC, washer, dryer,... View all property information
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    Chatham, Cape Cod 02659
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    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $1675 per week, including the cleaning fee Off-Season: $775 per week, including the cleaning fee Light and bright 4 bedroom home on quiet cul-de-sac in South Chatham. Comfortable furnishings throughout. Large upstairs bedrooms offer extra seating space too! Nice back deck off the... View all property information
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    South Chatham, Chatham
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This turn of the century Chatham rental house is located just 2/10th of a mile from Oyster Pond and 4/10ths of a mile from the downtown area where you can enjoy shopping, fine restaurants, outdoor band concerts, ball games and much, much more. It is a 4+ bedroom, 3 bath property. Amenities for a... View all property information
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    Chatham, Cape Cod 02633
    1 / 38
    West Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    ACCOMMODATIONS: 3 bedrooms plus den with 2.5 baths. Accommodating 8-10 people. Master suite: king bed w/en suite Guest room 1: queen bed Guest room 2: four twin beds (2 bunks) Guest room 3: den w/full bed Living room Dining room seats 8 (addition kitchen table seats 2) Two full baths total... View all property information
    Location Information
    West Chatham, Chatham 02633