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House Rentals and Beach Rentals in Chatham, MA

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    Travelers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 19
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 47
    5 of 5 bubbles (16) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 45
    5 of 5 bubbles (3) Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 9
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village. View all property information
    Location Information
    Chatham, Cape Cod 02633
    4 of 5 bubbles Reviewed October 1, 2014
    We enjoyed our stay at the condo in Chatham. It was comfortable for 3 people. It was clean and the kitchen was well stocked. Kris gave us excellent directions and suggestions.
    5 of 5 bubbles Reviewed August 14, 2014
    Having coffee each morning on the deck of this adorable cottage was one the highlights of my stay in Chatham. The view is terrific - of a lovely harbor that is called Mill Pond...
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    1 / 23
    5 of 5 bubbles (1) Excellent
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This bright and airy family-friendly home is just a 1/2 mile walk to this fabulous sandy beach where you can enjoy swimming both on Nantucket Sound or in the milder waters in the adjoining tidal creek. Ridgevale Beach is one of Chatham's most popular destinations for vacationing families. A clean,... View all property information
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed September 30, 2016
    We had a lovely weekend here while attending a family wedding. The house was comfortable and equipped with everything a family might need. The neighborhood is quiet and an easy...
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    1 / 41
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of quiet and accessibility for... View all property information
    Location Information
    Chatham, Cape Cod 02650
    5 of 5 bubbles Reviewed September 23, 2014
    Amazing home with a great owner who was 100 percent accessible our whole trip. Huge house, our party of 10 didn't even know one another was there. Highly recommend the location...
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    1 / 14
    5 of 5 bubbles (2) Excellent
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Chatham Beach house... walk to Harding's Beach in Chatham. Wonderful home, great for families! Outdoor Shower, wrap-around porch with patio furniture and grill, hammock to relax, Cable TV, DVD player (family movies on site), wifi included, full kitchen, laundry, garage, plenty of parking. Just... View all property information
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed October 8, 2016
    I had no idea how large my family had grown until I set out to organize a weekend in Chatham, MA. We started as a family of 3; 2 little girls and a dad. Now we're a family of 10...
    5 of 5 bubbles Reviewed August 19, 2016
    What a perfect rental! From the beginning, owner Sue was extremely helpful and responsive. The beautiful pictures on the website don't even do it justice- the house was beautiful...
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    1 / 20
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy this spacious home on the Monomoy River with glimpses of Pleasant Bay. Recently renovated, our home boasts a gourmet kitchen with granite counters, 6 burner Wolf cooktop and Sub Zero refrigerator and wine frig . The kitchen opens to a deck perfect for al fresco dinners watching the sunset.... View all property information
    Location Information
    Chatham, Cape Cod 02148
    5 of 5 bubbles Reviewed August 21, 2015
    This was a really beautiful home. An exciting mix of old and new, set on a lovely property, overlooking a lake. Sunrises and sunsets are breathless. Room enough for eight. State...
    5 of 5 bubbles Reviewed August 7, 2015
    Joy was a pleasure to work with. She was prompt with her communications to us. She explained everything we needed to do (having never done this before). The house was great...
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath home in Hardings Beach Hills is available to rent this season. With access to Buck's Creek flowing to Nantucket Sound, you can launch your kayak, fish or crab from the private association neighborhood dock and picnic area just... View all property information
    Location Information
    Chatham, Cape Cod 02669
    1 / 24
    North Chatham
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    #601 - The Salty Seashell: Great Holiday Deal! Beautiful private Chatham home in great location with a deck, patio, grill & yard!  You will fall in love with this bright and cheery Cape! Wide planked Pine Hardwood floors in Living room and Dining room. Wide Galley Kitchen, fully equipped, including... View all property information
    Location Information
    North Chatham, Chatham 02650
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    1 / 14
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible two bedroom, three full bathroom end-unit with gorgeous direct water views of Oyster Pond. Beautifully decorated with charming interior decor.... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 4 weeks ago
    Great property & perfectly located. Close to beaches, shopping & restaurants. The house is very beautiful and spacious. Quick check in and check out & quiet & secluded property.
    5 of 5 bubbles Reviewed February 17, 2017
    Our family visited Chatham numerous times over the years. We stayed at Chatham Bars Inn, Wequassett Resort, and other rentals. By far, Oysterpond Townhome Unit 32 was the best...
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    1 / 36
    North Chatham
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Come stay at: Donnadune. 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.... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 36
    North Chatham
    Studio, 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 (Rents Saturday - Saturday during peak season) 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... View all property information
    Location Information
    North Chatham, Chatham 02650
    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
    Location Information
    Chatham, Cape Cod 02633
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this traditional, yet well-appointed... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Location, location, location!! New, lovely furnished home in a quaint little Cape Cod village off Main Street. Minute(s) walk to shops, restaurants, movie theater, library, Chatham Bars Inn, Oyster Pond, Claflin Landing and Lighthouse Beach. Won't need to get in your car to vacation here! Chatham... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 16
    5 of 5 bubbles (1) Excellent
    West Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
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    About this property
    An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, one bedroom with 2 twin beds... View all property information
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed July 29, 2016
    It was a nice little spot for my boyfriend and I to get away for the weekend. Had no issues with the facilities. Please keep in mind the cabin isn't air conditioned. There are...
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    1 / 34
    5 of 5 bubbles (1) Excellent
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    ID #LAKE110 Lake front vacation home on Lovers Lake in Chatham in the Great Hill Neighborhood. [~]Heron Haven is a peaceful, spacious home in a beautiful lake front setting with many sought after features. This home sleeps 10 guests and boasts Central A/C and 4 living areas to spread out and... View all property information
    Location Information
    Chatham, Cape Cod 2633
    5 of 5 bubbles Reviewed June 16, 2014
    Our extended family stayed here last summer. We did a lot of research to find a place suitable for three families (grandparents, parents, and kids). We did site visits for the...
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    1 / 20
    Studio, 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
    Location Information
    Chatham, Cape Cod
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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
    Location Information
    Chatham, Cape Cod 02633
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    1 / 8
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    2017 Rental Rates ~ In Season, $1125 including cleaning fee No Off-Season 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 21
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, children's books and videos,... View all property information
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    South Chatham, Chatham 02659
    1 / 15
    4.5 of 5 bubbles (4) Very good
    Private Room, 5 Bathrooms, Sleeps 12 | Quick View
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    This lovingly restored Greek Victorian former bed and breakfast has 6 bedrooms and 5 full baths. Sleeps 12. Local lore has it that this property was floated over from Nantucket many years ago to its present site. Amenities include a Wolf range, granite counter tops, dishwasher, 2 cable TVs... View all property information
    Location Information
    Chatham, Cape Cod 02659
    3 of 5 bubbles Reviewed August 31, 2013
    Pros:1-Location few miles from the center of town, 2-Walking distance from forest beach (not good for swimming). 3-Accomedate large groups. Cons:1-It is an old...
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    1 / 25
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Location - Location - Location! Run, walk, or skip the loop in Chatham from this Family Cape Cod Vacation Rental home. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,700 - $3,250/week. It's just a 5 minute stroll to the town landing to put your kayak or canoe in... View all property information
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    Chatham, Cape Cod 02633
    1 / 33
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to: Endless Summer. Views-Views-Views! Pet Friendly Cape Cod Vacation Rental home with rooftop deck is just .2 to Ridgevale Beach. Peak Summer Weekly Rates:  (last week of June until the first week in September) $4,050/week Pet friendly! Enjoy water views from the main floor living areas... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $1775 per week with the cleaning fee ~~ Off Season Rate: $1050 per week with the cleaning fee. Weekly rentals from mid-JUNE to mid-SEPT This three bedroom home is a stones throw from Chatham's bike trail, so you can ride from your home all over the Cape. The Regional Middle School... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 26
    North Chatham
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Luxury Chatham Home, Water Views, Private Beach Peak Summer Weekly Rates: $5,150-$5,950 (Rents Saturday to Saturday during peak season) The home is set in a private neighborhood with tranquil views of Pleasant Bay and a one minute walk to a private association beach. Inside, the home is clean and... View all property information
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    North Chatham, Chatham 02650
    1 / 26
    North Chatham
    Studio, 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 AC mini split, WiFi, and new furnishings. Sleeps 4. Read on to learn more about our Chatham Mass Vacation Rentals Peak Summer Weekly Rates:  last week of June until the first week in September:... View all property information
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    North Chatham, Chatham 02650
    1 / 25
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to Sea Glass! This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,900/week. Warm water, sunsets, and miles of beach on Nantucket Sound awaits you just around the... View all property information
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    Chatham, Cape Cod 02659
    1 / 15
    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    About this property
    Beautiful Chatham Get-away! Located on a sandy, dead end lane, this cottage is the perfect Summer get-away. A large screened in porch fronts the cottage and is the perfect place for meals or evening game nights! Beautiful pine floors extend throughout the open floor plan. The living room has a... View all property information
    Location Information
    South Chatham, Chatham 02659
    5 of 5 bubbles Reviewed September 4, 2016
    As a first time traveller to Cape Cod this cottage was everything I imagined ! Beautifully decorated and everything you required . My family loved it and we had great fun playing...
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    1 / 8
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate ~ $1650 per week, including the cleaning fee Off-Season: $1200 per week, including the cleaning fee Comfortable summer rental home in a great central location! This three-bedroom ranch sits on a quiet street located in West Chatham. Just a quick drive in one direction to spend the... View all property information
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    Chatham, Cape Cod 02633
    1 / 31
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Pet Friendly.  Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500/week. Privacy abounds just off Main Street and the home even overlooks a... View all property information
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    Chatham, Cape Cod 02633
    1 / 1
    South Chatham
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Please contact Courtney... View all property information
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    South Chatham, Chatham 02633
    1 / 11
    South Chatham
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    2017 Rental Rate: $2275 per week, including the cleaning Off season, $1575 per week, including the cleaning Wonderful, clean, and comfortable home located in the quaint village of South Chatham. Enjoy your afternoons at the beach and your evenings in the bug free screened porch ! Within a quick... View all property information
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    South Chatham, Chatham 02659
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Welcome to #25 Stones Throw. This sunny end unit has everything you need for a relaxing vacation. There is a pool in the complex. There are no less that four beaches within a five minute drive. Salty's market is just down the hill, past the Truro Winery - also a great place for wine tasting. If... View all property information
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    Chatham, Cape Cod
    1 / 11
    North Chatham
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $1725 per week, including the cleaning fee ~~ Off Season: $1125 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field,... View all property information
    Location Information
    North Chatham, Chatham 02650
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    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    2017 Rental Rate: $1550 per week, including the cleaning fee~~~NO OFF-SEASON~~~ Enjoy your Chatham summer vacation in this light and bright vacation home. Located on a quiet side street, on the way to Ridgevale Beach, one of Chatham's most popular family beaches! Filled with bright colors and comfy... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    2017 Rental Rate: $1225 per week, including the cleaning fee. Weekly rentals from mid-JUNE to mid-SEPT Nicely decorated house on a quiet street near town and the Cape Cod Rail Trail. This is a very well maintained and comfortable home with the owner's original artwork throughout. Small yard in... View all property information
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    Chatham, Cape Cod 02633
    1 / 28
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    [~]This beautiful home with central a/c sleeps 8 and has the open and bright spaces of a contemporary classic. The first floor boasts floor-to-ceiling windows facing the deck which overlooks acres of private woods and the heated swimming pool. This gorgeous deck contains a new wicker L-shaped... View all property information
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    Chatham, Cape Cod 2633
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    South Chatham
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    2017 Rental Rate: In Season, $3175 per week, including the cleaning fee No Off-Season Weekly rentals from mid-JUNE to mid-SEPT Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home offers... View all property information
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    South Chatham, Chatham 02659
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    About this property
    Welcome to Harding's Beach Hills, where you will find Three Cheers, this charming cottage by the sea! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,000/week. This Chatham Cape Cod Vacation Rental offers ranch style living with A/C units in all 3 bedrooms,... View all property information
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    Chatham, Cape Cod 02633
    1 / 46
    Studio, 4 Bathrooms, Sleeps 14 | Quick View
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    Privacy and tranquility are enjoyed at this stunning in-town estate setting! 5 bedrooms (sleeps 14), Central AC, WiFi, and 3 levels of living space all make for a dream vacation in the heart of Chatham.​ Walk to beach and town! Peak Summer Weekly Rates:  last week of June until the first week in... View all property information
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    Chatham, Cape Cod 02633
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    West Chatham
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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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    Beachfront townhome! Sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor and Little Beach. Bike to town or the Monomoy Wildlife Refuge.​ Central AC and WiFi too. Peak Summer Weekly Rates:  last week of June until the first week in... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    Studio, 2 Bathrooms, Sleeps 11 | Quick View
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    About this property
    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 to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $2225 per week, including the cleaning fee ~~Off-season: $1525/wk, including cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely updated cottage located in the popular Harding's Hills neighborhood. Spacious master bedroom with cathedral ceiling and private bath. The... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    2017 Rental Rate: $2450 per week including the cleaning fee No off-season rentals Comfortable and airy post & beam home located in a quiet neighborhood near Harding's Beach. Tons of windows and skylights throughout bring in the sunlight! The eat-in kitchen overlooks the backyard gardens and walks... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Experience: Chatham Breeze. Luxury 4 bedroom, 3.5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $6,400/week Privately placed on just over a half acre of land in a peaceful setting, yet... View all property information
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    Chatham, Cape Cod 02633
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    2017 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 Updated, light & bright home located about 1/2 mile from downtown Chatham & Oyster Pond. New kitchen and furnishings throughout, as well as a newly... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
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    About this property
    2017 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL! ~~ Off-Season: $1400 per week including the cleaning fee !!! Weekly rentals from mid-JUNE to mid-SEPT Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and... View all property information
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    Chatham, Cape Cod 02633
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