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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 / 18
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come to the Cape and enjoy this 3 bedroom, 2 bath Chatham rental home. Take time to relax on the expansive deck with wonderful views of Mill Creek and Nantucket Sound or enjoy a BBQ on the gas grill. The open floor plan with adjoining kitchen, dining and living rooms creates a spacious area perfect... View all property information
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    Chatham, Cape Cod
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $1725, including the cleaning fee Off Season: $1225, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Traditional Cape Cod ranch with three bedrooms and central air conditioning. Great neighborhood for kids and about one mile bike ride down to Hardings Beach.... View all property information
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    Chatham, Cape Cod
    1 / 21
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom. Enjoy an outdoor dinner in your central courtyard accessed... View all property information
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    Chatham, Cape Cod
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Light and bright home with pretty marsh views! Great, central location, close to Hardings Beach and a quick drive into downtown Chatham! You will love the screened porch or back deck for relaxing. AC units in every bedroom for the hot days, if you aren't at the beach! One bedroom on the first level... View all property information
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    Chatham, Cape Cod
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2016 Rental Rate: $3225 including the cleaning fee~~~ Off Season: $2225 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Private, traditional style cape house in the Sears Point area of Chatham. It has a lovely sun porch, a large living room and a large yard with lots of... View all property information
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    Chatham, Cape Cod
    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    You will be just steps away from Forest Beach in this 3 bedroom, 3 bath home which boasts wonderful views of Nantucket Sound from the 3 decks, main living area and the 2 upstairs bedrooms. There is an adorable cottage/studio in the back that holds the 3rd bedroom along with the 3rd bathroom and a... View all property information
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    Chatham, Cape Cod
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate $1575 per week, including the cleaning fee! No Off season FRIDAY TO FRIDAY Bright, cheerful home with a peek of Pleasant Bay from the back deck. Swimming in Pleasant Bay is nearby at Jackknife Beach! This charming year-round home is impeccably maintained and has a finished lower... View all property information
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    Chatham, Cape Cod
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    1 / 1
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $3200 per week including the cleaning fee ~~ Off Season: $2000 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Location, location, location! A little over 1/2 mile to the Village of Chatham and 1/2 mile to the closest Beach~~kid-friendly Oyster Pond... View all property information
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    Chatham, Cape Cod
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Enjoy the views of Nantucket Sound from every floor of this recently updated, lovingly and meticulously maintained, 3 bedroom, 2 bathroom Chatham rental property. It is a perfect balance between having all of the modern amenities, with an open, light and bright feel while still maintaining the true... View all property information
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    Chatham, Cape Cod
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    2016 In Season Rental Rate... $3225/week, including the cleaning ~~ Off Season, $1725/week, including the cleaning. Classic, Cape Cod Home located in a peaceful, wooded setting but not far from the center of Chatham or the waters of Stage Harbor! Large & sunny kitchen, equipped with everything for... View all property information
    Location Information
    Chatham, Cape Cod
    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
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $2575 per week, with the cleaning fee~~~~Off-Season: $1775 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT FRIDAY TO FRIDAY RENTALS DURING SUMMER MONTHS Updated, light & bright home located about 1/2 mile from downtown Chatham & Oyster Pond. New kitchen... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 34
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    One of the most photographed Wind Mill homes on Cape Cod. Classic old world charm, coupled with all modern conveniences located near the beach and town. The Stony Hill Mill, constructed with 100 year old beams, river rock and barn board, is truly Cape Cod at its finest. This large stately home is... View all property information
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    North Chatham, Chatham
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This wonderful 4 bedroom 2 bathrooms vacation home is located at a cul de sac just off Old Queen Anne Road near Main Street Chatham. Enjoy the spacious deck on a nice summer night, roast marshmallows or fix you a s'more by the fire pit or enjoy the ping pong table or foose ball table at the game... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 15
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2016 Rental Rate ~ $4200 per week, including the cleaning fee ~ Off-Season ~ $2000 per week, including the cleaning fee ~ Charming, antique, 5 BR home located on Chatham's 'loop', steps to the water and Stage Harbor Yacht Club. Enjoy the breathtaking views of Stage Harbor and Stage Harbor... View all property information
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    Chatham, Cape Cod
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $2100 per week including the cleaning fee ~~ Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great four bedroom home located close to Chatham's Bike Trail, and near a fresh water pond. Located at the end of a cul-de-sac with a nice... View all property information
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    Chatham, Cape Cod
    1 / 12
    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    2016 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
    Location Information
    South Chatham, Chatham
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    1 / 11
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
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    • x
    About this property
    2016 Rental Rate: $2275 per week including the cleaning fee SPECIAL RATES FOR: Aug 20th...$1875, including cleaning Aug 27th....$2075 per week with cleaning included Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Wonderful, clean, and comfortable home... View all property information
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    South Chatham, Chatham
    1 / 10
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    • x
    About this property
    2017 Rental Rate: $2275 per week, including the cleaning fee Off-Season (June only): $1675/wk including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Located in a quiet neighborhood, 1/4 mile from Forest Beach. Charming home with a comfortable living room. Bright & spacious sun room... View all property information
    Location Information
    South Chatham, Chatham
    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
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Waterfront
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    • x
    About this property
    2016 Rental Rate: $3925 per week including the cleaning fee ~~ Off-Season: $2260 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious home with fabulous views of Little Mill Pond, next to Chase Park, and just a few blocks from Chatham Village! This rental has... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    2016 Rental Rate: $2100 per week, with the cleaning fee ~~No Off-Season~~ Welcome!! This roomy Cape sits up on a hill located just off of Cockle Cove Road on a quiet one way drive. Just .4 mi to Cockle Cove Beach. There are three bedrooms and 2 full and one half baths. The master BR is en-suite... View all property information
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    Chatham, Cape Cod
    1 / 12
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    2016 Rental Rate: $3975 per week including the cleaning fee No Off Season Classic Cape walking distance to Harding's Beach; the entire family can handle the quick walk down to popular, kid-friendly Hardings Beach. This home has six air conditioning units as well as high speed internet. A giant... View all property information
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    Chatham, Cape Cod
    1 / 23
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This ideally situated, spacious 5 bedroom, 4 bathroom classic antique home is just steps away from gorgeous Lighthouse Beach and just a short distance to downtown Chatham as well as the famous Mitchell River bridge where fishing is bountiful. Outside, you can enjoy the deck overlooking your own... View all property information
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    Chatham, Cape Cod
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Terrace
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    • x
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    About this property
    4 Bedroom, very bright, beachy home with SEPARATE guest house! This home comes equipped with AC, fully stocked kitchen and deck to enjoy your wine/coffee. Not to mention a private enclosed lawn to relax or play on. Located in the HEART OF TOWN. Walk out the driveway and you will find yourself... View all property information
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    Chatham, Cape Cod
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    2016 Rental Rate: $2000 per week, including the cleaning fee Off-Season: $1425 per week, including the cleaning fee Wonderful two bedroom summer rental, just steps to the center of Chatham! Filled with comfortable upscale furnishings, it offers plenty of living space and a great location near the... View all property information
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    Chatham, Cape Cod
    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    2016 Rental Rate: Pre-season (May 28-June 18) $1,200 per week ~~~IN SEASON: $1800 per week (June 18-Sept 10) ~~~Post-season (Sept 10-Oct 15th) $1,200 per week Off-season (subject to Owner's prior approval) $800 week $175 MANDATORY cleaning fee per lease Weekly rentals from mid-JUNE to mid-SEPT... View all property information
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    Chatham, Cape Cod
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    2016 Rental Rate: $1900 per week including the cleaning fee ~~ Off Season: $1400 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Comfortable home in a wonderful location near Chatham Village! Let the children play in the huge yard or walk the short distance to Chatham's... View all property information
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    Chatham, Cape Cod
    1 / 9
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This traditional 2 bedroom 1 bathroom Chatham cottage is located in a quaint neighborhood and is just 4/10ths of a mile to Pleasant Street Beach. Amenities include a window AC unit in each bedroom, cable TV (with basic cable only), microwave, outside dining table with gas grill and an enclosed... View all property information
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    Chatham, Cape Cod
    1 / 12
    4 of 5 stars (1) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    This rental property boasts both a main house and fully equipped cottage, great for extended family or friends. The main house has 3 bedrooms and 1 full bath. Amenities include central AC on the first floor and window AC units in the upstairs twin bedroom, washer, dryer, dishwasher, TVs with... View all property information
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    Chatham, Cape Cod
    1 / 17
    5 Bedrooms, 6 Bathrooms, Sleeps 11 | Quick View
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    • ?
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    • x
    About this property
    2016 Rental Rate: $7550 per week including the cleaning fee Off Season: $5850 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It... View all property information
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    Chatham, Cape Cod
    1 / 15
    5 of 5 stars (6) Excellent
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Satellite TV
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    • Outdoor Dining Area
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    • ?
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    • x
    About this property
    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes.... View all property information
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    South Chatham, Chatham
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    2016 Rental Rates ~ In Season, $1100 including cleaning fee Clean rental home located just 1/2 mile to Hardings Beach or Oyster River Boatyard. Fresh paint and furnishings throughout make this small yet comfortable rental a great buy! Good size living room with high ceilings make it appear larger... View all property information
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    Chatham, Cape Cod
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    2016 Rental Rates: $2475 per week, including the cleaning fee ~~ Off-Season: $1375 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Bright and cheerful summer cottage, walking distance to the warm waters of Hardings Beach! Located in Hardings Hills, there is also an... View all property information
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    Chatham, Cape Cod
    1 / 10
    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    About this property
    2016 Rental Rate: $9350 per week, including the cleaning fee The entire family will enjoy this gorgeous, newly built 4+ BR home with a private association path down to Ridgevale Beach! The beach is close, there is a path across the street that takes you to a bridge to the beach; the heated pool in... View all property information
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    Chatham, Cape Cod
    1 / 25
    5 of 5 stars (2) Excellent
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • Smoking allowed
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    About this property
    Lovingly renovated in winter 2013 and designed by a New York couple, this 4-bedroom, 3-bathroom colonial saltbox home evokes the style and taste of classic Americana, decorated with vintage finds and unique antique pieces. Whether you’re on a family vacation, couples getaway, or a reunion with... View all property information
    Location Information
    South Chatham, Chatham
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Patio
    • Satellite TV
    • Washer
    • Internet Access
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
    • x
    About this property
    2016 Rental Rate: $1775 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Here is a great deal!! Clean and spacious 3 bedroom, home that sleeps 8 people comfortably, with plenty of room to spread out. This centrally located home is convenient to the bike trail, South... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Patio
    • Satellite TV
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    2016 Rental Rate $2975 per week, including the cleaning fee Off Season, $1975 per week, including the cleaning fee Gorgeous, light & bright beach home located right down the street from family-friendly Hardings Beach. Plenty of room to relax and enjoy your Chatham vacation with two living areas and... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Secure Parking
    • Washer
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Outdoor Dining Area
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Chatham, Cape Cod
    1 / 15
    4 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our Pleasant Street home is a charming 3 bedroom, 2 bath year-round home which is located at 320 Pleasant Street in South Chatham and it can comfortably accommodate up to 8 people. It is only a 2 minute walk to Nantucket Sound, the warm water side of Cape Cod! There is no beach sticker required... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 17
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This 3 bedroom, 3.5 bath Chatham rental cottage is situated at the end of a cul-de-sac abutting conservation land and only 8/10ths of a mile to popular Ridgevale Beach. Enjoy your day at the beach and then relax on the deck overlooking a wooded area. Amenities include central AC, washer, dryer,... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Porch
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Short Drive to Everything! Our cape home offers lots of space for your family. 3/4 mile to Pleasant Bay Beach, 1 minute walk to Ryder’s Cove boat yard, few minutes walk to tennis courts and Cape Cod bike trail. 5 minutes drive to town center. Close to playground and baseball field - home of the... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Waterfront
    • DVD Player
    • Grill
    • Parking
    • Internet Access
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our home is the perfect spot for your family to enjoy beautiful Cape Cod and award winning Chatham. Located on a picturesque and VERY quiet street you can stroll to Pleasant Street Beach or Forest Street Beach. The yard offers the perfect place for the kids to play, the upper and lower decks offer... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Washer
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    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
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    • Smoking allowed
    • ?
    About this property
    2016 Rental Rate: $6250 per week, including the cleaning fee Off-Season $4450 per week, including the cleaning fee The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings and bed sets. The spacious open floor... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 15
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rates: $5850 per week, including the cleaning fee ~~ Off season: $2850 per week, including the cleaning fee (last 2 weeks of June $3850 per week, including the cleaning fee) Weekly rentals from mid-JUNE to mid-SEPT This spacious, fully equipped home on 3 acres is completely surrounded... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 15
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    2017 Rental Rate: $3225 per week, including cleaning fee No Off Season Beautiful, clean beach home located a quick half mile to Chatham's Ridgevale Beach. Plenty of space to spread out with the open floor plan, as well as the newly finished walk out basement. Huge, grassy back yard...perfect for... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 5
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • DVD Player
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    2016 Rental Rate ~ $3050 per week including the cleaning fee. ~~ Off-Season: $2200 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This recently renovated four bedroom beach cottage is in the heart of the beautiful and kid-friendly Hardings Hills area. It offers a... View all property information
    Location Information
    Chatham, Cape Cod