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Chatham House Rentals

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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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    5 of 5 bubbles (3) Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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
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    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed 30 September 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 / 47
    5 of 5 bubbles (20) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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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    Chatham, Cape Cod 02659
    5 of 5 bubbles Reviewed 31 October 2016
    We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every...
    5 of 5 bubbles Reviewed 13 September 2016
    A Slice of Heaven. From the moment you pull into the driveway, you will not be disappointed. This home is perfect in every way......location is close to main routes...
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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
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    Chatham, Cape Cod 02148
    5 of 5 bubbles Reviewed 22 August 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 8 August 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 / 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
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    Chatham, Cape Cod 02650
    5 of 5 bubbles Reviewed 23 September 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
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    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed 8 October 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 19 August 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 / 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
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    Chatham, Cape Cod 02633
    1 / 13
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    NOTE - Not available to book until mid Feb deadline for family and friends to sign up. Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 30
    South Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house has been beautifully updated... View all property information
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    South Chatham, Chatham 02659
    1 / 34
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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 02650
    1 / 24
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    #602 - Port View Home:  Nantucket sound awaits you in this sweetie beach house. Pull in the driveway, look to the left ... All you see is OCEAN. Magnificent Nantucket Sound with white sandy beach just waiting on you to put down the beach blanket and take a dip! Port view home offers great living... View all property information
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    South Chatham, Chatham 02659
    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 21 February 2017
    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 17 February 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
    4 Bedrooms, 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
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    North Chatham, Chatham 02650
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    South Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2700-$3,400 A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0.6 mile)! Central air, WiFi, a... View all property information
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    South Chatham, Chatham 02659
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    338 Seapine Road CHATHAM, ID# 104736 Waterfront 3 bedroom home overlooking Bassing Harbor and Fox Hill with the outer beach beyond. Located on a cul de sac near Eastward Ho! Country Club in North Chatham, the home is a classic Cape in style. Water access for kayaking in Pleasant Bay and beyond.... View all property information
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    Chatham, Cape Cod 02633
    1 / 48
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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
    Location Information
    Chatham, Cape Cod 02659
    5 of 5 bubbles Reviewed 31 October 2016
    We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every...
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    1 / 32
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Come stay at: Cape Sunsations! Views- Views- Views from every room! Updated Luxury Waterfront Cape Cod Vacation Rental Home In Chatham, offering over 3100 square feet of living space. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,900/week. Updated Luxury... View all property information
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    Chatham, Cape Cod 02633
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    This perfectly situated Chatham rental is welcoming to you and your four legged friends. Located close to Shore Road, you and your guests will enjoy the best of being close to the water and close to Main Street. Walk to town on sidewalks and enjoy the amazing shops and restaurants. Walk to the... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Charming house completely renovated in the perfect location - central to all that Chatham and the Cape have to offer. Enjoy the downtown Main Street, restaurants, beaches, Chatham A's baseball, outdoor concerts and the fishing pier only a short stroll away. When you return for the evening enjoy the... 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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    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... View all property information
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    Chatham, Cape Cod 02633
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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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    5 Bedrooms, 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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    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    2017 Rental Rate: $9350 per week, including the cleaning fee Call about Off-Season! 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 29
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    WATERFRONT! Come stay at: Milhaven, This Cape Cod Vacation Rental is located in Chatham's Old Village and is right on Mill Pond. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,500 - $3,900/week. The Old Village is popular for its historic nature and architectural... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 12 August 2014
    Wonderful New England cottage right on Mill Pond, with terrific views. The 3-bedroom main house has all the amenities and the studio with a bath is just across the patio and is...
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    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 4 | 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:$2,000/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
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    ON THE WATER ...<BR><BR>* Beautiful water views! <BR>* Back decks open to mesmerizing views of Emery Pond <BR>* Hammock and patio furniture chosen for comfort and relaxation!<BR>* Direct access to pond from backyard. <BR><BR>* Clean swimmable pond.<BR>* Bass fishing plentiful!<BR>* Gas grill.<BR>*... View all property information
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    Chatham, Cape Cod 02633
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    North Chatham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Pet Friendly! Quintessential Cape Cod 5 Bedroom Chatham Vacation Rental home with beach access.  A/C units in bedrooms and main living area.  Wifi too. Peak Summer Weekly Rates:  last week of June until the first week in September: $3500- $4,600/week. Welcome to North Chatham- Here you will find a... View all property information
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    North Chatham, Chatham 02650
    1 / 33
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Featuring gorgeous gardens and outdoor spaces to explore, a luxurious and updated interior, and all the comforts of home, this beautiful rental has it all! Ideal for two guests, this would be a fantastic place for a honeymoon, couples getaway, or even a relaxing solo retreat. Nestled in a quiet... 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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    Come stay at: Seashell Beach Cottage! Beach front vacation rental cottage in Chatham! Peak Summer Weekly Rates:  last week of June until the first week in September: $2,800/week. Stay at this 2 bedroom cottage located right on the beach in Chatham, the best of Cape Cod. Beautiful views! Perfect for... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 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 02633
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    North Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Captains Walk. This traditional Cape Cod Vacation Rental just 1 mile to downtown Chatham Peak Summer Weekly Rates:  last week of June until the first week in September: $3,000/week. Private setting on quiet street perfect for kids to ride bikes. AC Units in the Master bedroom and the... View all property information
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    North Chatham, Chatham 02650
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $2775 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Lovely, updated condo with water-views of the Nantucket Sound. Light and bright with comfy upscale furnishings. Located on a quiet side street in... View all property information
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    South Chatham, Chatham 02659
    1 / 47
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    Come stay at: Sand Simeon. 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: $12,000- $16,525/week. This luxury home is pet friendly with a private pool, central... View all property information
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    Chatham, Cape Cod 02633
    5 of 5 bubbles 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 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $2150 per week, including the cleaning fee Off-Season: $1525 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious three bedroom ranch in quiet neighborhood near Hardings Beach. Recently updated, it is filled with comfortable furnishings and has... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    You will enjoy easy times in this 3 bedroom 2 bath Cape set on a hilltop. This very well-equipped house is at the end of a cul-de-sac and offers complete privacy, a large deck with grill, outdoor shower, and ample parking. It has a contemporary open and airy floor plan with cathedral ceilings and... View all property information
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    Chatham, Cape Cod 02633
    3 of 5 bubbles Reviewed 19 August 2016
    We are a family of four travelling from the UK and stayed at the property for one week in July. Chatham was a relaxing week after our whirlwind tour of Florida and New York. We...
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    1 / 30
    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 - like most of our Cape Cod Vacation Home Rentals - with over 1600 sq. ft. of finished... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    2017 Rental Rate: $2225 per week including the cleaning fee ~~ Off-season $1525 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming home located in terrific central area of North Chatham. Walk to Ryder's Cove boatyard. Beautifully landscaped, fenced-in, private... View all property information
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    Chatham, Cape Cod 02633
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    2017 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 02633
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Enjoy "Summer Remedy" this traditional, updated Cape Cod Vacation Rental home in Chatham is located just a short walk to Ridgevale Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,300/week Wifi and Central air.  Enter the front door into Living Room with... View all property information
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    Chatham, Cape Cod 02633
    1 / 48
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Come Stay at: Good Times! Welcome to your Beach House! This Cape Cod Vacation rental home is located in Chatham in the Harding's Beach Hills (just .3 mile to Harding's Beach and .2 mile to The Buck's Creek Association dock and picnic area). Peak Summer Weekly Rates:  last week of June until the... View all property information
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    Chatham, Cape Cod 02633
    1 / 22
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful water views of Pleasant Bay from this charming, sprawling ranch which has 4 bedrooms and 3 baths. There is a spacious living room, dining room, large deck, all with spectacular views overlooking Pleasant Bay. Amenities include AC (central throughout + wall unit in master queen), washer,... View all property information
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    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 18 August 2016
    Just reading the description of this home can't do it justice! The location was perfect for us: high on a bluff overlooking the Sound, so we got lovely breezes even on the few...
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    1 / 12
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $2175 per week, including the cleaning fee Off Season: $1575 per week, including the cleaning fee Wonderful, updated ranch located in a private neighborhood and centrally located to all that Chatham has to offer! Open and airy floor plan with newer furnishings throughout. Tons of... View all property information
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    Chatham, Cape Cod 02633
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 27
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to The Little Caper. This updated 4 bedroom, 2 bath vacation rental home in Chatham is well maintained and a great spot for making family memories. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,800/week and just $1,900 in Sept and October!! Just under a... View all property information
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    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 18 July 2016
    This was our 6th year vacationing in Chatham and our 2nd at the Palmer Dr. location. We LOVE Palmer Dr. It is the perfect home in the perfect location. It is close enough to the...
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    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
    1 / 11
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $2800 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will love this 4 bedroom home near Ridgevale Beach! Located at the end of a dirt road with water views of a freshwater pond and... View all property information
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    Chatham, Cape Cod 02633
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 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
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    Chatham, Cape Cod 02633
    1 / 52
    8 Bedrooms, 11 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Rising majestically over Eldridge Point, overlooking Oyster River, Harding’s Beach, and Nantucket Sound, this extraordinary estate features the largest private shoreline in Chatham. Watch glorious sunsets while swimming in your infinity edge pool; or cook dinner in the outdoor kitchen while friends... View all property information
    Location Information
    Chatham, Cape Cod 02633