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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.
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Gorgeous ocean views and a large sunroom await at this comfortable and roomy Cape Cod home. Even better, the beach is just across the street! Set in a peaceful, family neighborhood, this house is near Tom's Neck, has easy access to the popular preserve with a hiking trail and native wildlife.... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Cape cottage near wonderful Hardings beach Nice location about a third of a mile to popular, scenic Harding s beach. Typical knotty pine style cottage with central living room and enclosed rear porch open to the picnic patio. Has a small front deck too. Sleeps 6. $1500 per week plus $60 handling... View all property information
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    Chatham, Cape Cod 02633
    1 / 9
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 7
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    73 Main Street, Unit #8 Charming second-story condominium apartment located right across the street from Lighthouse Beach. Views of the beach from deck off the living room. Walk across the street to Lighthouse Beach and also within walking distance to the Village. NO pets accepted. $1350 per week,... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Well maintained two bedroom home that sleeps 4.One queen and 2 twins with a pullout in the den. Located in scenic North Chatham. A five minute drive from downtown Chatham, Chatham Bars Inn, the Lighthouse, Chatham Seaside Links golf course and the baseball field which hosts the Cape Cod Baseball... View all property information
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    Chatham, Cape Cod 02650
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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 02633
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    393 STONY HILL ROAD CHATHAM Charming and completely renovated cottage, 7/10 of a mile to Scatteree Beach and the Cow Yard Landing and under 2 miles to Main St., Chatham for shopping, dining, and ice cream! This adorable one bedroom, air conditioned cottage has vaulted ceilings, exposed beams, a... View all property information
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    Chatham, Cape Cod 02633
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    1 / 13
    West Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Near Hardings Beach Just a short distance to Harding s Beach (2/10 of a mile) from this charming 4 bedroom, 3 bathroom Cape Style home. Deeded path over the dunes to the Beach! $3500 per week in season with a $200 Cleaning Fee plus a $60 Handling Fee and tenant has choice of either a $55 Vacation... View all property information
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    West Chatham, Chatham 02669
    1 / 11
    West Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Short walk to Oyster River Boatyard this two bedroom two bath home is just about a mile to Harding Beach. Sleeps 4 to 6 with one king, one queen, one single and one queen sleep sofa. Wireless internet, central a/c, enclosed outside shower and private deck for outside dining. Weekly summer... View all property information
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    West Chatham, Chatham 02669
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham! Peak Summer Weekly Rates:last week of June until the first week in September: $2,200/week. Offering Central AC & Wifi with over 1600 sq. ft. of finished living space, 3 bedrooms, 2 full bathrooms, and a large... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Roll out of bed and onto the shore of one of the most beautiful beaches on Cape Cod! Hardings Beach is miles of fun, family friendly, coastline and this beautiful classic turn of the century Chatham rental house is located less than 3 minutes walk to the sand! This charming turn of the century... View all property information
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    South Chatham, Chatham 02633
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Lovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated kitchen and an awesome location! The beach is just a walk across the street from this beautifully landscaped Shore Road home. This home is located on the first fairway of... View all property information
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    Chatham, Cape Cod
    1 / 14
    5 of 5 bubbles (1) Excellent
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    15 Bobbies Lane CHATHAM Cottage is charming and updated. Located in South Chatham. Central A/C, convenient to shopping, beaches, and golf. Only 1/2 mile to Nantucket Sound. Screened in Porch, WiFi, 1 Queen, 2 singles and 2 Queen Sofa beds. Sleeps 6. Please contact Courtney Blankenship at... View all property information
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    South Chatham, Chatham 02633
    1 / 11
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    16 SEA STRAND LANE (ID#109551) CHATHAM Charming and comfortable! Located in a quiet area within a short driving distance to both Hardings and Ridgevale Beaches. Air conditioning cools the home with units in every bedroom, including first floor master bedroom. WiFi, outdoor shower, washer/dryer,... View all property information
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    West Chatham, Chatham 02669
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Experience Cape Cod living at our 4-bed, 2-bath Chatham vacation rental in a quiet, quaint wooded neighborhood. Hop on your bike (or into the car) and be at the beach or downtown Chatham in minutes! The home’s wooded deck/backyard and its finished basement—with a pool table, foosball, playroom and... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 25
    5 of 5 bubbles (2) Excellent
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    South Chatham, Chatham 02659
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Whether you're settling in for a sun-filled beach vacation or seek a quiet seaside escape over the cooler months, this picturesque 3-bedroom, 2-bathroom home promises a charming and relaxing stay on the Cape year-round. Beautiful pine floors and old-world wood furnishings are set off by soft,... View all property information
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    Chatham, Cape Cod 02633
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    1 / 20
    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This Cape Cod Vacation home Rental in Chatham is just yards out the back yard to Forest Road Beach. Peak Summer Weekly Rates:last week of June until the first week in September: $2,850/week. Central A/C for those hot summer nights. You can smell the salt water from this ranch style home with four... View all property information
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    South Chatham, Chatham 02659
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. Peak Summer Weekly Rates:last week of June until the first week in September: $3,400/week. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm summer sun, you are sure to have a... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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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    4.5 of 5 bubbles (4) Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    Pet Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. Peak Summer Weekly Rates:last week of June until the first week in September: $6,500/week. This spot is a boater’s paradise! From kayaking to... 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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    **NEW WEEK JUST MADE AVAILABLE.** Monday, August 1 - Monday, August 8th. Located in one of the most desirable areas of Chatham, this 3 bedroom, 2 bathroom classic Cape home is just a short walk to Chatham Light and has direct access to a path that winds through the dunes to Lighthouse Beach and... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Cute cottage only 1 mile to Hardings Beach! Genuine 2 bedroom, 2 bath Cape Cod Cottage! Well maintained and appox. 1 mile to Hardings Beach in Chatham. Relax and dine in the screened porch which expands across the front of the cottage. This neighborhood is located off Barn Hill and a short... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This tastefully furnished 3 bedroom, 3 bathroom home is situated in a lovely neighborhood in Chatham Village. It is less than a mile from the shops and restaurants on Main Street and even closer to the Chatham Fish Pier and Chatham Bars Inn. This home is open and airy and beautifully decorated with... View all property information
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    Chatham, Cape Cod 02633
    1 / 35
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Tradition and modern luxuries collide at this lovely Cape Cod home. You'll find high-end furnishings inside and beach access nearby! You're on a quiet lot near a salt marsh and just a half mile from Forest Beach and less than two miles from lovely Taylors Pond. Post-and-beam construction can be... View all property information
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    Chatham, Cape Cod 02659
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
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    This wonderful house located in beautiful North Chatham is a great place to spend your Cape Cod vacation! It is decorated with classic and clean taste and completely ready for you to arrive and enjoy! The porch is a great spot to enjoy a cup of coffee in the morning- there is a nice backyard area... View all property information
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    Chatham, Cape Cod
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    52 PLEASANT STREET NEW for 2015 SEASON CENTRAL a/c. Easy access to Pleasant Street Beach. The property has 3 bedrooms, two with 2 single beds and one with a queen size bed all on one level. Amenities include an enclosed porch, outside shower and WIFI. This property rents for $1700 per week in... View all property information
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    Chatham, Cape Cod 02633
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:last week of June until the first week in September: $3,875-$3,975/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... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Recently renovated cottage in sought after Cockle Cove beach neighborhood. Walk or bike 4/10ths mile to warm, sandy & family friendly town beach on Nantucket Sound. Direct waterfront location on tidal Taylors Pond, with stunning views and access to owner's private dock for kayaking & boating into... View all property information
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    South Chatham, Chatham 02360
    1 / 13
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    122 CHATHAM CREST DRIVE Four bedroom three bath home located in a quiet part of Chatham. Two queen beds and 4 single beds this home sleeps 8. Outdoor shower, high speed internet, wifi and cable tv are some of the attributes of this vacation home. Three quarters of a mile from Ridgevale beach.... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    19 Glendon Way, S. Chatham Casual knotty pine summer cottage just 1/2 mile to Pleasant Street Beach. This 3BR/1BA single level cottage is located in a nice quiet neighborhood of South Chatham. Convenient to shopping - just a 10 minute drive into town. $1150 per week in season. Please contact... View all property information
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    South Chatham, Chatham 02659
    1 / 39
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    $13,500.00/week Peak Season (7/15 - 8/19) $12,500.00/week On Season (7/1 - 7/15 and 8/19 - 9/2) $11,500.00/week Off Season Gorgeous panoramic views of Stage Harbor, Nantucket Sound and Outermost Harbor from every room in the house. Private dock, multiple decks, a swimming pool and an incredibly... View all property information
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    Chatham, Cape Cod 02633
    1 / 29
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    This very spacious 4 bedroom, 4.5 bathroom newer home includes use of the association pool and tennis court. There is a 1st floor en suite bedroom with a king sized bed. The 3 other 2nd floor bedrooms are also en suite. Enjoy your meals outside on the beautiful deck in a private setting. Other... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    North Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks: $2,000 Please note: This property is part of a larger estate, and is only available to rent individually in the months outside of July and August Located in historic North Chatham and just 0.2 miles... View all property information
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    North Chatham, Chatham 02650
    1 / 32
    North Chatham
    7 Bedrooms, 5 Bathrooms, Sleeps 24 | Quick View
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    Historic North Chatham Estate. Sleeps 20, private beach! (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $15,200 - $16,900 "Shore Acres", an extra-large historic Chatham estate...a spectacular venue for family vacations, extended families, multiple families vacationing together,... View all property information
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    North Chatham, Chatham 02650
    1 / 37
    North Chatham
    8 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    Chatham Family Compound Sleeps 16 Walk to Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900 Located just 0.2 miles from the beach, this is an ideal estate for multi-generational families or other large groups to spend time together with plenty of space on nearly three acres to... View all property information
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    North Chatham, Chatham 02650
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Shore Road, Chatham. Sleeps 12, harbor views, walk to everything! NEW Listing for 2017! Peak Summer Weekly Rates: $5,850 - $6,500 Quintessential Chatham home located in a highly desirable area. Enjoy beautiful views of Chatham Harbor from the large upper level deck. This property features 4... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Spacious Cape Cod Beach House with Central air and WIFI. Steps to the ocean with deeded access to private beach.​ Peak Summer Weekly Rates:last week of June until the first week in September:$3000-$3200/week. Special deal $1275 off season! Relax and unwind at this 3 bedroom, 2 bath home in Chatham... 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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    2017 Rental Rates: $3275 per week, including the cleaning fee Off Season: $2275 per week, including the cleaning fee Walk to town in minutes from this recently updated ranch on Highland Avenue! Light and bright with new furnishings throughout, this adorable home features wireless internet, central... View all property information
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    Chatham, Cape Cod 02633
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2017 Rental Rates ~~ In Season: $2650 per week, including the cleaning Off Season: $1950 per week, including the cleaning Enjoy all Downtown Chatham has to offer but also enjoy the peace and quiet of staying off the beaten path! This darling rental sits about 1 block from the shops and restaurants... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Sunny and Bright Condominium in North Chatham! What a great spot to base yourself from while visiting Chatham! Large windows let in lots of sun to the open floor plan second level condo in Nickerson Corners. Convenient to restaurants, town, shopping, beaches and the bike trail, you will easily... View all property information
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    North Chatham, Chatham 02650
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $3500 per week including the cleaning fee Off-Season: $2200 per week including the cleaning fee WEEKLY RENTALS FROM MID-JUNE TO MID-SEPTEMBER Three-night minimum during the Off-Season: $350 a night including the cleaning Light and bright, this spacious four bedroom is walking... View all property information
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    Chatham, Cape Cod 02633
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    ref Additional amenities include: outdoor shower: enclosed, bedding rm2: twin day bed w/trundle ~ 1st floor, bedding rm1: queen ~ 1st floor, bedding rm4: queen ~ 2nd floor, beach umbrella, a/c units: 5: 1 in lr, and 1 in each bedroom, tub and shower: 1 ~ 2nd fl., priceclass: under $3000, lobster... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $2800 per week including the cleaning fee ***FRIDAY TO FRIDAY RENTAL*** ~~~ Off-Season: $2200 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean... View all property information
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    North Chatham, Chatham 02650
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $3,500/week Off Season (5/1 - 6/30 and 9/2 - 10/31) $5,200/week Peak Season (7/1 - 8/18) $4,900/week Shoulder Season (8/19 - 9/1) Enjoy your vacation in this private setting with a water view and only a short walk to downtown Chatham. This well appointed, light and bright, 4 bedroom, 2 1/2 bath... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Outdoor Dining Area
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    Paradise Found at this special retreat in this Cape Cod Vacation home Rental in Chatham called the Heron’s Nest! Peak Summer Weekly Rates:last week of June until the first week in September: $4,600/week. This spacious , Four Bedroom, 3 bath luxury Chatham Rental will surely delight you in every... View all property information
    Location Information
    Chatham, Cape Cod 02633