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House Rentals in Chatham, MA

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    1 / 46
    5 of 5 stars (14) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    North Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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
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    Chatham, Cape Cod 02633
    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
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    Chatham, Cape Cod 02669
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
    1 / 9
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Waterfront
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    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 stars Reviewed 1 October 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 stars Reviewed 14 August 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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    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | 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
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    West Chatham, Chatham 02633
    1 / 13
    North Chatham
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    2016 rental Rate: $7700 including the cleaning fee~~ Off-Season: $3850 per week, including the cleaning fee ~ For 10 people only, lower level not available for Off-Season rentals~~ A large recently renovated 6 bedroom home located in the exclusive Cannon Hill Estates of North Chatham. This location... View all property information
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    North Chatham, Chatham 02650
    1 / 15
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Freshly painted Cape Cod home tucked just off of Route 28 near the Chatham/Harwich line. Very convenient location with a quick walk to two great restaurants and .7 mile walk to Forest Beach, and Pleasant Street Beach.<BR><BR>House includes an open living/dining area, a first floor master bedroom... View all property information
    Location Information
    Chatham, Cape Cod 02659
    4 of 5 stars Reviewed 26 August 2014
    Adorable, comfortable home. Rooms and closets very spacious. Clean, well maintained. Children, 13, 13 & 10 loved it! Would def' return! Paula
    4 of 5 stars Reviewed 16 September 2013
    Very clean, smaller home about a 5 minute drive from quaint Chatham's main restaurant and shopping area. Kitchen and bathrooms are dated but the full interior has a fresh coat of...
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    1 / 47
    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home offering 6 bedroom 6.5 bathrooms. Peak Summer Weekly Rates:last week of June until the first week in September: $16,525/week. This luxury home is pet friendly with a private pool, central a/c, linens,wifiand more. In historic... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars Reviewed 27 May 2015
    This house is great. Has all the appliances you could want. Different coffee options, 2 sets of large washers and dryers, 3 dishwashers, pool table, big screen TV, pool with...
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    1 / 9
    North Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2016 Rental Rate: $2800 per week including the cleaning fee ~~~ 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 from large deck. Short walk to... View all property information
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    North Chatham, Chatham 02650
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Shared Outdoor Pool...
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    About this property
    Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. Peak Summer Weekly Rates: last week of June until the first week in September: $3000-$3,600/week. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars Reviewed 6 July 2014
    We loved to stay in this luxurious and wonderful house! Anything is very clean and you don´t miss anything. Thank you for the nice "start bags", that is more than one can...
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    1 / 44
    5 of 5 stars (1) Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
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    About this property
    Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are bright and nicely appointed with... View all property information
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    South Chatham, Chatham 02659
    5 of 5 stars Reviewed 2 May 2016
    Plusses: * Kitchen is fully equiped and the stove is big and of excellent quality. * Showers have a lot of power. * Good size house (big living room, separate dining room, big...
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    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2016 Rental Rate: $3275 per week, including the cleaning fee Off Season: $2275 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. This home is 1/2 mile from the quaint town center and... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 17
    North Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    2016 Rental Rate: $5050 per week including linens and cleaning! ~~ Off-Season: $3900 per week including cleaning and linens Weekly rentals from mid-JUNE to mid-SEPT Gorgeous five bedroom home in secluded North Chatham neighborhood. This home features hardwood floors, WIFI and central air. Upscale... View all property information
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    North Chatham, Chatham 02650
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Quintessential Cape Cod Vacation Rental Cottage in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates: last week of June until the first week in September: $1,350/week. Enjoy this Cape Cod beach cottage with casual coastal decor. A/C units in living area and bedrooms and Wifi too.... View all property information
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    Chatham, Cape Cod 02633
    1 / 19
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Grill
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    • Patio
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    • Pet-friendly
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    About this property
    Welcome to our entirely renovated 'old Cape' cottage, with a sunny, open floor plan, brand new appliances and furnishings, washer/dryer and central air. After the beach, rinse off in the private outdoor shower before relaxing on the sunny patio. The Space: Create cherished family memories in our... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars Reviewed 7 November 2015
    Wonderful house, very nice quiet location within easy reach of beaches. House very clean with everything that we needed. Would highly recommend.
    5 of 5 stars Reviewed 29 September 2015
    This accommodation is very well appointed and has everything one could need. Chatham is an ideal base for exploring the whole of Cape Cod. You can walk from the property to a...
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    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $1775 per week with the cleaning fee ~~ Off Season Rate: $1250 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
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    Chatham, Cape Cod 02633
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $1950 per week including the cleaning fee ~~ Off-Season: $1400 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL!!!! 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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    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Why pay the new Homeaway/VRBO surcharge? Book with confidence and save when you book direct with Pretty Picky. OWNER SPECIAL -- Remaining Peak Weeks Just Reduced! New listing for 2016 Luxuriously renovated home across the street from beach, 5 minutes from Chatham Village. 2016 Peak Summer Weekly... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    5 Bedrooms, 6 Bathrooms, Sleeps 11 | Quick View
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    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 02633
    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Coastal, Seaside home offering Central air has plenty of room for 3 couples or 2 families. Walk to beach and town! Peak Summer Weekly Rates:last week of June until the first week in September:$2100- $2,850/week. This Cape Cod Vacation Rental in Chatham has an open floor plan with 3 bedrooms on the... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars Reviewed 3 June 2016
    We had a wonderful stay in this home. We were pleasantly surprised with all new appliances in the kitchen, which was very well stocked, making it easy to make meals at home...
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    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
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    Chatham, Cape Cod 02633
    1 / 26
    North Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Completely renovated condo in North Chatham. Enjoy this lovely condo with all amenities including Central A/C mini split, wifi, and new furnishings. Sleeps 4. Peak Summer Weekly Rates: last week of June until the first week in September: $1,250/week. Conveniently located in a very quiet area of... View all property information
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    North Chatham, Chatham 02650
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $3575 per week including the cleaning fee. ~~ Off-season: $2575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming home right on Seaview Street - a short walk to downtown Chatham, or Chatham Bars Inn! This home has lovely furnishings throughout,... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    North Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 mile to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 2 miles to Main St., Chatham for shopping,... View all property information
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    North Chatham, Chatham 02650
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. Peak Summer Weekly Rates: last week of June until the first week in September: $2,000/week Located in a residential area and convenient to the Cape Cod Bike trail, and the Chatham Airport... View all property information
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    Chatham, Cape Cod 02633
    1 / 18
    South Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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
    Location Information
    South Chatham, Chatham 02659
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate: $2175 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
    1 / 12
    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    South Chatham, Chatham
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 Rental Rate ~ $1650 per week, including the cleaning fee Off Season, $1150 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
    Location Information
    Chatham, Cape Cod 02633
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy the downtown location of this Cape Cod Vacation Rental Home in the village of Chatham. Peak Summer Weekly Rates:last week of June until the first week in September: $3,950/week. Convenient to Chatham shops, restaurants, new Orpheum movie theatre and Oyster Pond. Families love the proximity to... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 02633
    1 / 20
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    2016 Rental Rate: $8900 per week, including the cleaning fee Off-Season: $6100 per week, including the cleaning fee Just listed, this stunning waterfront home features a private waterfront setting on Chatham's exclusive Stage Island. Enjoy the fabulous water-views of Stage Harbor from almost every... View all property information
    Location Information
    Chatham, Cape Cod 02633
    West Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    West Chatham, Chatham 02633
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    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 / 11
    North Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2016 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
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    North Chatham, Chatham 02650
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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 02633
    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 02633
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    key #39 Additional amenities include: outdoor shower: enclosed, dist. to downtown: 2 miles, fans: 3, area: north chatham, a/c units: 3 - 1 in each br, priceclass: under $3000, year built: 1980, lobster pot, distance to beach: 1 mile or under, name of beach: jackknife beach/pleasant bay,... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    2016 FRIDAY TO FRIDAY Rental: In Season $3950 per week with the cleaning fee ~~~ Off Season $2650 per week with the cleaning fee included Weekly rentals from mid-JUNE to mid-SEPT You cannot beat the fabulous views from the decks of this sprawling Cape Cod retreat! There is a lot of space for two... View all property information
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    Chatham, Cape Cod 02633
    1 / 36
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Pet Friendly! Refreshed 5 bedroom 2 bath Cape Cod Vacation Rental home in downtown Chatham! Peak Summer Weekly Rates: last week of June until the first week in September: $5,500/week Wonderful in-town Chatham oasis. Park your car and walk to all things downtown Chatham has to offer including band... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    North Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Completely renovated condo in North Chatham. Enjoy this lovely condo with all amenities including Central A/C mini splits, wifi, and everything new. Peak Summer Weekly Rates: last week of June until the first week in September: $1,250/week. Conveniently located too. Situated in a very quiet area of... View all property information
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    North Chatham, Chatham 02650
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    North Chatham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2016 Rental Rate: $3225 per week, with the cleaning fee ~~Off-Season: $2225 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Spacious 5 bedroom on quiet cul-de-sac in prestigious North Chatham. Walk to beach, Band concerts, baseball games, Movies, and fish pier. House has... View all property information
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    North Chatham, Chatham 02650
    1 / 22
    5 of 5 stars (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    0.1 mile from a popular summer Nantucket Sound beach… can walk or ride or /access to private beach via path along marsh just steps away from the house quiet family area… ranch / cottage style house with summer beach flavor with views of Taylor Pond 1 bathroom / eat in kitchen / deck / Weber gas... View all property information
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    South Chatham, Chatham 02659
    5 of 5 stars Reviewed 2 weeks ago
    We absolutely loved our stay at this charming seaside home, it feels like someones primary residence not a rental. The home is bright, open and beautifully appointed, plenty of...
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    1 / 28
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Location – Location-Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Peak Summer Weekly Rates:last week of June until the first week in September: $3,900 - $4,100/week. Whether you Enjoy cocktails on the traditional front porch, read a... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    2016 Rental Rate: $4270 per week including the cleaning fee. This is a FRIDAY TO FRIDAY RENTAL only. Off-Season: $3270 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming Cape-style home on Main Street in Chatham's Old Village. Located just blocks from the shops... View all property information
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    Chatham, Cape Cod 02633
    1 / 25
    3 Bedrooms, 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: $2,600 - $3,200/week. SPECIAL - AUG 27-Sept 3 only $1425!! GREAT DEAL and beautiful time to be in... View all property information
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    Chatham, Cape Cod 02633
    1 / 37
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Pet Friendly! Charming, fully renovated Sea Captain's home, located in downtown Chatham. Peak Summer Weekly Rates: last week of June until the first week in September: $4500-$5,000/week Enter through the sun porch offering extra dining- directly into the gourmet kitchen with a granite counter... View all property information
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    Chatham, Cape Cod 02633
    4 of 5 stars Reviewed 1 October 2014
    Our family of four (parents with our 20-something daughters) rented this nicely renovated historic home in a downtown location... just blocks from the ocean. We went to Chatham...
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