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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
    €3,462
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    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    €3,206
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    3 Bedrooms / 4 Bathrooms / Sleeps 10
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    €1,740
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    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    €1,649
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    251 Joshua Jethro PET FRIENDLY Wonderful three bedroom three bath Cape-style home in the Riverbay community of Chatham with central A/C. The kitchen and all three bathrooms have been recently renovated and the first floor bathroom includes a whirlpool jet bathtub. The first floor bedroom has a... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    WATERFRONT RENTAL PROPERTY!! This rental has a stairway that leads down to a lovely private sandy beach area on Pleasant Bay and a Shared Float Dock for your boat! Relax and enjoy the lovely water views from the expansive deck and the house. Spectacular views of Ryders Cove, Pleasant Bay and the... View all property information
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    North Chatham, Chatham 02650
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    1 / 19
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Lovely bright home with waterviews and central A/C in North Chatham Stunning, beautifully furnished and decorated home with central A/C and views of Pleasant Bay out to the Atlantic is located in a lovely area of North Chatham. This reverse floor plan home with the living areas on the second floor... View all property information
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    Chatham, Cape Cod 02633
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    €1,237
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    1 / 10
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    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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    Chatham, Cape Cod 02633
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    1 / 16
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Charming, updated sea captain's home in Old Village just off Main Street, with views of Little Mill Pond. Short walk to Lighthouse Beach, Friday night band concerts, shopping and restaurants. Beautifully furnished and appointed, surround-sound entertainment, gas fireplace, outdoor shower, and... View all property information
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    Chatham, Cape Cod 02633
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    €1,351
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    1 / 7
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    COZY AND COMFORTABLE!! This Chatham home has three bedrooms and two baths with central air conditioning, wireless internet, flat screen television, master bedroom with private bath. Enjoy peace and tranquility in this quiet residential neighborhood of Chatham. This home is centrally located and a... View all property information
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    Chatham, Cape Cod 02633
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    €2,290
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
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    About this property
    Lovely 2 bedroom home located in a prime location between Lighthouse Beach and Chatham Village. Charming, well maintained home in a fabulous location in Chatham s Old Village. The home is less than 1/2 mile to both Lighthouse Beach and the quaint village of Chatham s shops and restaurants. This... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    The Avenues;, a very desirable, popular summer area with a private association beach area on a tidal salt water inlet. The house has recently had renovations. Freshly painted, floors refinished, nicely appointed and furnished. Very large lot, large front porch, a.c. units in some rooms. 1 Queen... View all property information
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    South Chatham, Chatham 02672
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    €1,099
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    SHORT WALK TO TOWN AND CAPE LEAGUE BASEBALL GAMES! This 3 bedroom/2 bath home is located on a quiet side street and is just 7/10's of a mile to the Chatham Angler's ballfield, town playground and just a bit farther to Main Street. This well maintained home is bright and updated with remodeled... View all property information
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    Chatham, Cape Cod 02633
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    €4,030
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    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    A RENTAL PROPERTY THAT YOU WILL WANT TO RETURN TO YEAR AFTER YEAR! Beautiful four bedroom/3.5 bath home loaded with charm and comfort. Property has central air conditioning, lovely furnishings and beautiful decor, updated kitchen with center island and double ovens, lovely dining room, comfortable... View all property information
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    Chatham, Cape Cod 02633
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    €160
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Smoking allowed
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    • x
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    About this property
    Our Cranberry Way home is a charming 2 bedroom, 2 bath (one new) year-round home which is located at 47 Cranberry Way in South Chatham and it can comfortably accommodate up to 6 people. It is only 0.6/mi. to Nantucket Sound, the warm water side of Cape Cod! It is a pet-friendly home (with an... View all property information
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    Chatham, Cape Cod 02659
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    €641
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    1 / 37
    4 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    180+ photo gallery available upon e-request. This exquisitely furnished four bedroom home is located on the Ocean side of Shore Road with an easy walk to Chatham's beaches, Fish Pier, Lighthouse, town center, outdoor band concerts and fine restaurants. Just minutes walk from The Chatham... View all property information
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    Chatham, Cape Cod 02633
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    €1,099
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    1 / 19
    South Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    SIMPLY ADORABLE! Updated rental property located at the end of a quiet cul-de-sac. Two minute walk to bike trail access (no need to drive to get on the bike path) and 9/10's mile to beautiful Nantucket Sound - Cockle Cove Beach area. Cozy and comfortable with many new furnishings and so many... View all property information
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    Location Information
    South Chatham, Chatham 02659
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    €1,832
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    1 / 12
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Shared Outdoor Pool...
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    About this property
    185 Indian Hill Road -Property ID: 99369 SUMMER RATE REDUCED FOR 2015 .Gorgeous home very close to the Cape Cod Bike Trail and School House Pond! This home offers access to pools, tennis courts, fitness center, and activities at Ocean Edge Resort & Golf Club in Brewster, MA at an additional charge... View all property information
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    Chatham, Cape Cod 02633
    From
    €1,466
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    1 / 11
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    About this property
    Pet friendly home with central air Comfortable 4 bedroom cape on a quiet street in Riverbay Estates. Convenient to Schoolhouse Pond and Jackknife Cove beach on Pleasant Bay. This home has central air conditioning, an enclosed outside shower, and is PET FRIENDLY. This property rents for $1400 -... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    3 Bedrooms / 4 Bathrooms / Sleeps 9
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    • Dishwasher
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    About this property
    WELCOME TO SUMMER! This property just screams Summer and is just under 1/2 mile to Forest Beach! This enchanting home is light and bright and is nicely furnished. Spectacular first floor master bedroom with cathedral ceiling, loads of light, comfortable window seat and cozy reading area with two... View all property information
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    South Chatham, Chatham 02659
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    €2,840
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    1 / 21
    South Chatham
    5 Bedrooms / 5 Bathrooms / Sleeps 11
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    • Air Conditioning
    • Balcony
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    • x
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    About this property
    148 Stage Coach Drive, South Chatham -Property #79285 WEEKLY RATE REDUCED $600.Beautiful spacious 5BR/4.5BA located in South Chatham. Convenient to shopping, golf and movies. Close to beach, 1.3 miles. Main level has large open kitchen and dining area, office, sunroom, seating area with fireplace... View all property information
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    South Chatham, Chatham 02659
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    1 / 14
    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    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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    Chatham, Cape Cod 02633
    From
    €916
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    1 / 13
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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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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    Chatham, Cape Cod 02633
    From
    €177
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    1 / 4
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Conveniently located South of Route 28 and less than a mile to popular Ridgevale Beach, this 2 bedroom, 2 bathroom Town House style condominium is absolutely pristine. The unit has been totally renovated with features including Pella sliders to the two decks, tiled bathrooms, a spacious living room... View all property information
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    Chatham, Cape Cod 02669
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    €1,099
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    West Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    SHORT DRIVE TO BEACH AND BIKE PATH!! This rental property is a gem! It has so much to offer! Located on a quiet cul-de-sac and just one mile to Hardings Beach (beautiful Nantucket Sound beach) and 2.5 miles to the center of town. Also short ride to the bike path! Window air conditioning units in... View all property information
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    West Chatham, Chatham 02669
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    €824
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    South Chatham
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Address: 50 Cockle Cove Ridge, South Chatham -Property ID: 95538 This nicely kept South Chatham Condo is located in the Cockle Cove Ridge complex---right off of Route 28 and just under a mile to Cockle Cove Beach on Nantucket Sound. The first floor offers a living room and an eat-in kitchen. Slider... View all property information
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    South Chatham, Chatham 02659
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    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    • x
    • x
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    About this property
    455 Shore Road, Chatham - Property ID: 105467 Wonderful Captains House located on the highly desirable Shore Road in Chatham with water views of Chatham Harbor and walking distance to Claflin Landing Beach and Chatham Village! Wonderful Captains House located on the highly desirable Shore Road in... View all property information
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    Chatham, Cape Cod 02633
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    €3,206
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    1 / 15
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Waterfront
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    • Pets allowed
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    About this property
    105 Wood Carver Knoll, Chatham - ID# 106342. Spectacular waterfront home in Chatham overlooking Oyster Pond! Central Air, gourmet kitchen with espresso machine, keurig and more. Enjoy the deck with incredible views of Oyster Pond, the church steeples of Main St, tidal marshes and bird life. Bright... View all property information
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    Chatham, Cape Cod 02633
    From
    €1,924
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    WALK TO TOWN AND LIGHTHOUSE BEACH....LOCATED IN THE HEART OF THE OLD VILLAGE! this charming renovated antique home is just a short walk to Lighthouse Beach and to Town! The perfect location in Chatham! Central Air Conditioning, wireless interent access, comfortable interior with new living room... View all property information
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    Chatham, Cape Cod 02633
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    €1,008
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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
    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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    Chatham, Cape Cod 02633
    From
    €2,473
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    GREAT IN TOWN LOCATION!!! Walk to restaurants, shops, Chatham Angler's ballgames, town playground and Oyster Pond Beach area. CENTRAL AIR CONDITIONING! Master bedroom with private bath, cable television and gas fireplace. Master bath with new shower and large tub. Great mahogany deck and outdoor... View all property information
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    Chatham, Cape Cod 02633
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    €1,466
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    COMFORT AND AFFORDABILITY! Reserve this three bedroom/2.5 bath rental and you will enjoy the true Summer feel of this house! Property is very light and bright, well maintained and nicely furnished. Offers central air conditioning, wireless internet, master bedroom with private bath and lower level... View all property information
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    Location Information
    Chatham, Cape Cod 02633
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    Schoolhouse Pond just 1/10 mile! Charming custom remodeled Cape Cod home, 1/10 mile to Schoolhouse Pond Beach--perfect for freshwater beach lovers. First floor offers open kitchen / living area with wall AC unit and one first floor queen bedroom with a ceiling fan. Second floor has three bedrooms... View all property information
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    Chatham, Cape Cod 02633
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    €962
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
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    11 CHATHAM BARS AVENUE Very attractive and spacious second story condominium. Located in the true heart of the village, and just a short walk to Claflin Landing beach. $1750 per week in season + $120 cleaning fee and $55 Vacation Rental Damage Coverage Fee (VRD), $60 Handling Fee, (fees... View all property information
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    Chatham, Cape Cod 02633
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    €2,565
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    1 / 25
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
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    68 Summer Hill Lane CHATHAM Charming Large Post and Beam Cape Style home privately nestled on a quiet lane. 4 bedrooms and 3 bathrooms. Open kitchen/dining/living room floor plan. Spacious Great Room with cathedral ceilings, central A/C, master suite away from main living area. Private courtyard,... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    Beautifully updated ranch in Chatham Gorgeous fully renovated home in a quiet neighborhood. Open floor plan with a lovely kitchen featuring granite countertops. Central air conditioning, hardwood floors and wireless internet are just a few of the amenties for a comfortable vacation. Lovely... View all property information
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    Chatham, Cape Cod 02633
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    €16,030
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    6 Bedrooms / 7 Bathrooms / Sleeps 12
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    Rare, Elegant Chatham Waterfront Compound $18,500 PRIME SUMMER WEEKLY RATE This exquisite North Chatham estate is located in one of Chatham's most premier neighborhoods on Old Harbor Road. Set far back from the road on over 2 acres, this property provides stunning elevated views of Chatham Harbor,... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    Short Walk to Private Association Beach. This is a spacious 3 bedroom, 4 ½ bath home contemporary home on Stage Island with central air conditioning, wireless internet, washer/dryer, fully equipped updated kitchen with granite countertops, dining area, living room with comfortable furnishings, tv... View all property information
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    Chatham, Cape Cod 02633
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    €870
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    GREAT LOCATION DIRECTLY ACROSS FROM LIGHTHOUSE BEACH!! Sought after Old Village location, immaculate 1 bedroom condo with one bedroom/one bath, open small kitchen/living room area, queen size bed in the bedroom and pullout queen sofa in the living room. Enjoy the waterviews of Light House Beach,... View all property information
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    Chatham, Cape Cod 02633
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    €2,519
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    6 Bedrooms / 2 Bathrooms / Sleeps 11
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    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the 'loop' just around the bend from Stage Harbor. Wonderful area for walking and biking and a tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy yard is... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    454 Training Field Road CHATHAM Lovely updated 3 bedroom home in close proximity to Pleasant Bay and Jackknife Cove beach. Just a few minutes drive to the quaint downtown village of Chatham. This home rents for $1600 per week in season. All rates plus $60 Handling Fee and $55 Vacation Damage... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    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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    Chatham, Cape Cod 02633
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    €2,931
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    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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    Chatham, Cape Cod 02633
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    $1150/week–High Season–lower other times Foote-steps Chatham Charmer - Weekly Rentals The charm of a Cape Cod cottage with all the amenities of home. Relaxation and conveniences on a private circle with idyllic nature views... Enjoy our enclosed porch overlooking the salt marsh and a short (4/10... View all property information
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    Chatham, Cape Cod 02659
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    €392
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    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    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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    Chatham, Cape Cod 02633
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    North Chatham
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Be one of the lucky ones to enjoy the picturesque waterviews and great location of this North Chatham rental property. Located on a quiet cul-de-sac with a path that leads down to the water (sorry no beach area!) with a lovely spacious yard and a picket fence covered with roses...a true Cape Cod... View all property information
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    North Chatham, Chatham 02650
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    €4,214
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    155 LIME HILL ROAD CHATHAM Large and lovely 4 bedroom home built to a very high standard. Just a short distance to Chatham Village and all it has to offer. Beautiful yard and grounds, this home is a joyful place in the summertime. Offering 4 comfortable bedrooms, a generous kitchen and central... View all property information
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    Chatham, Cape Cod 02633
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    €641
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    4 Bedrooms / 4 Bathrooms / Sleeps 11
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    • Air Conditioning
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    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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    Chatham, Cape Cod 02633
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    €1,649
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    South Chatham
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    THIS IMMACULATE HOME HAS SO MUCH TO OFFER! FOREST BEACH IS JUST 9/10'S MILE AWAY. It is very light and bright, well maintained and full of charm! Portable air conditioning units for each bedroom, wireless internet access and new flat screen television above the mantle in the living room plus... View all property information
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    South Chatham, Chatham 02492
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    South Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Spacious 3 bedroom with large yard on cul-de-sac! Sunny and breezy rental property with plenty of living space. Close to Cape Cod Rail/Bike Trail. Large air conditioned famly room/dining room, opens to a fully equipped kitchen with new stove, microwave and eat-in area. Sunny, comfortable living... View all property information
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    South Chatham, Chatham 02659
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    €1,145
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
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    190 Countryside Drive - ID# 104736. Lovely 4 bedroom home in Chatham Charming 4 bedroom home in a peaceful area with a lovely fenced in yard. Just a short drive to Jackknife Cove beach on Pleasant Bay and a short distance to Monomoy River for kayaking and canoeing. School Houe Pond is a half mile... View all property information
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    Location Information
    Chatham, Cape Cod 02633