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Chatham Vacation Rentals

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    Travelers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    Cape Escape Chatham Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 53
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Chatham 1 Bedroom Beachfront Old Village1 / 9
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Beach Chic Cape Escape! Chatham 5 Star Private-Newly Renovated 5m walk to beach1 / 54
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 15, 2016
    What a unique & wonderful house in Chatham!  John & Ruby are really superb hosts, very accommodating, making sure we were all set… to our delight, John even texted to let...
    Reviewed May 2, 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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    About this property
    Newly renovated kitchen with quartz “Sea Glass” countertops, backsplash and Nantucket farm sink. Truly a well equipped cooks kitchen. This year round low allergen, open concept home has 3 bedrooms, 2 newly updated baths, a large two level outdoor deck with electric retractable awning, creating a...
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    Chatham, Cape Cod 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    All New Cottage in Chatham Near Hardings Beach1 / 19
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Grill
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 16, 2018
    Recently rented this cottage for a week and it was wonderful. Everything was set up so nice and the renting process was made seamless by the owners. It felt like we were the...
    Reviewed November 7, 2015
    Wonderful house, very nice quiet location within easy reach of beaches. House very clean with everything that we needed. Would highly recommend.
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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...
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to ChathamBeachCruiser! Relax in our 5 bedroom home with central air. The entire house is equipped with all new furniture in June of 2016 and a few antiques (including a coffee table made from a real ship’s wheel). The house sits at the end of a private drive with plenty of parking. This...
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    North Chatham, Chatham 02650
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 13, 2018
    Great house—-convenient to beach and all Chatham attractions— very responsive owner— comfortably furnished and super clean— great vacation!
    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...
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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,...
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    West Chatham, Chatham 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beautiful sunsets in Chatham!1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Outdoor Dining Area
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 22, 2018
    We had a wonderful time in Chatham. Joy's house was beautiful. Spacious and really well designed with lovely views over a lake; and located on a quiet private road. The outside...
    Reviewed July 29, 2018
    My son proposed to his girlfriend on Jackknife Beach (a short walk away) while we were on vacation here. It’s a beautiful home. Would highly recommend it if your looking for a...
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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 . Extra bonus: a second dishwasher and frig in the laundry room offof the kitchen!...
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    Location Information
    Chatham, Cape Cod 02148
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Grill
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2017
    Our stay at Pleasant Forest Shores was awesome! The cottage was very clean, had a sizable living room & kitchen and was located within a quiet neighborhood. It was also about...
    Reviewed July 1, 2017
    We actually stayed in cottage #2 but they appear to fairly similar. I used to vacation in Chatham as a kid in the late 60's and early 70's. These cottages are VERY reminiscent...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    Location Information
    South Chatham, Chatham 02659 1525
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Captain's Haven1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Yard
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    West Chatham, Chatham 02633
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ides of Marsh1 / 12
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Internet Access
    • Parking
    • Porch
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    $1150/week-High Season-lower other times Foote-steps Chatham Charmer - Weekly Rentals The charm of a Cape Cod cottage with all the amenities of home. Relaxation and conveniences on a private circle with idyllic nature views... Enjoy our enclosed porch overlooking the salt marsh and a short (4/10...
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    Location Information
    Chatham, Cape Cod 02659
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed September 24, 2017
    Would totally stay here again. Super clean & comfy, plenty of room for 3 adults & a dog, nice quiet neighborhood with friendly neighbors, close to beach. Had one small...
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quiet Lakeside Cottage - Ideal for Couple1 / 14
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Cable/satellite TV
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    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 18, 2018
    We had a wonderful stay at Helene's cottage. Great location for bike riding, swimming and canoeing. Our host provided many local areas of interest in the form of a binder...
    Reviewed August 8, 2018
    This cottage is a one bedroom on White Lake, nestled amount trees and other cottages. It is charming and a very comfortable way to spend a week in the Chatham, MA area. The...
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    About this property
    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming, kayaking and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage...
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Quintessential Cape Cod Vacation Home in N.Chatham1 / 41
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    • Balcony
    • Grill
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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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...
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    Chatham, Cape Cod 02650
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Private Contemporary Cape Set on a Hilltop1 / 20
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    Had a great stay with my family. It was quiet, relaxing, very well stocked with everything we needed and conveniently located. Would highly recommend.
    Reviewed August 19, 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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    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...
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    cape cod charming family friendly chatham cottage .01 mile to Cockle Cove Beach1 / 22
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Outdoor Dining Area
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2016
    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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    About this property
    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...
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    Location Information
    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 22, 2017
    I admit I ended up here somewhat by accident, but it was a fortuitous accident. Not only is this small cottage colony (5 cottages) perfectly located to get to a variety of...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    Location Information
    South Chatham, Chatham 02659 1525
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Former Chatham Bed and Breakfast1 / 12
    (4)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Outdoor Dining Area
    • Washer
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    About this property
    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...
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    Location Information
    Chatham, Cape Cod 02659
    Private Room - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Our highly rated & reviewed 3 bedroom 1 & 1/2 bath home is nestled on a quiet side street just 3/10 tenths of a mile from one of the best beaches in Chatham...Forest Beach. Our comfortable home is 1100 square feet; and is updated & modern with Air Conditioning, Wi-Fi & a 50'' LCD TV... yet it...
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    South Chatham, Chatham 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Brand new custom built beauty in Chatham, walk to Ridgevale Beach! (linens included) Peak Summer Weekly Rates: $6,300 - $7,200 Rents Saturday to Saturday during peak season NEW Listing for 2018!  This brand new custom home provides a luxurious vacation experience just a short walk from...
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    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Friday to Friday Rental This cottage is converted out of an a barn built in 1792. The upstairs bedroom has a full bed and the downstairs bedroom has a day bed (2 twin beds). This cottage is not for everyone. The entrance to the upstairs bedroom is steep and 18' wide. You can see it next to the...
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    South Chatham, Chatham 02659
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    South Chatham, Chatham 02659
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath (+ outdoor shower) 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...
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    Location Information
    Chatham, Cape Cod 02669
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    About this property
    COMING IN 2019: BRAND NEW HEATED SALT WATER POOL! This perfectly situated Chatham rental features everything one is looking for in a Cape Cod rental. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to town on sidewalks...
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham!  Offering Central AC & free WiFi with over 1600 sq. ft. of finished living space, 3 bedrooms, 2 full bathrooms, and a large den there is plenty of space for you to relax in with the entire family.    Welcome...
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    We have a duplex with two side-by-side units with two bedrooms each. Little to no sound passes between the units. Do you like to walk on the beach? We have the best location for it in North America (maybe the world)! A 3 minute walk from the door and you can walk for miles, across a gorgeous salt...
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Location, location, location. Enjoy this classic 2 bedroom, 1 full bath Cape beach cottage less than 2/10ths of a mile to popular Ridgevale Beach. Amenities include window AC units in the queen bedroom as well as the kitchen/living room area, washer, dryer, dishwasher, cable TV (including sports...
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    195 Cedar Street Chatham - ID# 106000 Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, this is a wonderful newly renovated home including a fabulous new kitchen with sunny breakfast nook. Living room,...
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    Location Information
    Chatham, Cape Cod 02633
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This traditional, 3 bedroom, 1.5 bathroom Chatham vacation cottage has beautiful views of the Cockle Cove salt marsh and is just steps to Cockle Cove Beach and the warm waters of Nantucket Sound. Amenities include AC splits (one in each queen bedroom), Wi-Fi, cable TV, DVD player, washer, dryer,...
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    Chatham, Cape Cod 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 minutes to Harding Beach, 10 minutes to downtown Chatham This bright and cozy 4 bedroom, 1.5 bathroom home is located in a quiet neighborhood just minutes from downtown Chatham. Walk to a scenic town landing on Oyster Pond River, or drive to popular Harding Beach in less than 5 minutes. Oyster...
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    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 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. Warm water, sunsets, and miles of beach on Nantucket Sound awaits you just around the corner. The proximity to the beach is so close, you will frequent beach visits and be pleased with...
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    Chatham, Cape Cod 02659
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Come stay at: Misty Meadow! Enjoy this lovely condo with all amenities including Central AC mini splits and free WiFi Conveniently located too. Situated in a very quiet area of North Chatham offering private conservation views from this charming one bedroom, first floor, end unit condo. An open...
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    North Chatham, Chatham 02650
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,310 - $6,750 (Pets Considered)  Rents Saturday to Saturday during peak season Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham...
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    Chatham, Cape Cod 02633
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    CONDO NEXT TO COCKLE COVE BEACH IS JUST 0.9 MILES AWAY!1 / 17
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed August 18, 2014
    rental was everything we expected. Place was clean and in a great location. There were bikes, boogie boards and beach chairs for your use.
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    Cockle Cove Beach is just 0.9 miles away from this light & bright Chatham Condominium located at Cockle Cove Ridge. The Chatham Village center is just 3 miles away for shopping, dining, Chatham A's baseball games, & the bandstand. The entry level of this 2 bedroom, 2 bath home features a living...
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    Chatham, Cape Cod 2659
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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 Rents Saturday - Saturday during peak season 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...
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    North Chatham, Chatham 02650
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    North Chatham, Chatham 02650
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Vacation Rental (3388)1 / 20
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed August 22, 2018
    The location of the house was perfect, with family in Orleans and Chatham. We were just steps from the beach, and there were a ton of great restaurants and shops within a short...
    Reviewed August 19, 2016
    We loved this houseIt had everything we needed Great house screen porch and deckMaybe 1 more tv would be good
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    About this property
    This 4 bedroom, 2 bathroom South Chatham rental home is only .2 mile to Pleasant Street Beach and .3 mile to Forest Beach. The recently renovated kitchen has granite countertops and new stainless appliances. The screened-in porch with vaulted ceiling overlooks a wooded area making it a peaceful...
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    Chatham, Cape Cod 02659
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 11 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $8600 per week Off-Season: $6650 per week Click for More Photos, Map, and Availability Calendar This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It features...
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    Chatham, Cape Cod 02633
    Rental Home - 5 Bedrooms, Sleeps 11
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Come stay at: The Cozy Beach Cottage! Chatham Vacation Rental Cottage at the beach! Get away to this 1 bedroom cozy cottage located right at the beach in Chatham, the best of Cape Cod-Sleeps 4. Perfect for a relaxing, romantic getaway, this cottage is steps from the sand, and is ready for your...
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    Chatham, Cape Cod 02633
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8 Quick View
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    About this property
    key # 158 Additional amenities: 1/2 Bath 2, A/C Units 4 ~ 1 in each BR, Area Town, Bedding rm1 King Ensuite ~ 2nd Fl., Bedding rm2 Queen ~ 1st Fl., Bedding rm3 Two Twins ~ 2nd Fl., Bedding rm4 Two Twins ~ 2nd Fl., Bedrooms 4.00, CD, Dist. To Downtown 3/4 mile, Distance to Beach 7/10 mile, Fans 4,...
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    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, Sleeps 8
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    55 Sears Point Road Chatham Cape Cod- The Sears Point House1 / 39
    (1)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    Reviewed August 11, 2018
    We enjoyed a lovely week at this great home. Our nine member family had plenty of room and two other family members were also able to join for a night or two. Chatham is...
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    About this property
    Enjoy this classic Cape Cod Style waterfront home with sparkling water views, a private beach, and large yard in Chatham. Over 180 degree views of Stage Harbor, Nantucket Sound, Monomoy Island, and the Atlantic Ocean beyond. Pet Friendly! Sleeping 12 there is plenty of space for everyone. Each...
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    Chatham, Cape Cod 02633
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Exquisitely Renovated Chatham Sea Captain's Home Linens included, brand new furnishings, hot tub Peak Summer Weekly Rates: $4,500-$5,500/week This immaculate newly renovated home is set close to everything in Chatham.  The property is located about a mile from the center of Chatham, and about a...
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    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    • Outdoor Dining Area
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! So wanting for a nice clean quiet apartment unit close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the...
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    South Chatham, Chatham 02659 1525
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gorgeous views of Nantucket Sound, Ridgevale Beach and Bucks Creek from this charming 2 bedroom, 1 bath authentic Cape cottage. Located just steps to popular Ridgevale Beach, the only public beach with watersports rentals and a snack bar, this cottage has one bedroom with a full size bed and...
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    Chatham, Cape Cod 02669
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chatham Cape Cod Waterfront Vacation Rental (8927)1 / 18
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Reviewed September 3, 2016
    Chatham Vacation rentals followed our guidelines and helped us find the perfect vacation house. Home had exquisite views of Pleasant Bay - private pier was a bonus House was...
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    Magnificent waterfront home with views of Pleasant Bay, North Beach and the Atlantic beyond. This updated and well-appointed 4 bedroom, 3 1/2 bath home is located in an association neighborhood, water-front home with breathtaking views of Pleasant Bay, North Beach and the Atlantic beyond. The...
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    Chatham, Cape Cod 02633
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Enjoy staying in the heart of Chatham Village in this new,er tastefully appointed 2 bedroom, 2.5 bath 1,300 sq. ft. home. Downtown Chatham is just steps away where you can enjoy shopping, fine restaurants, band concerts, ball games and much, much more. This home is only 2/10ths of a mile to...
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    Chatham, Cape Cod 02633
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to: Sandy Paws! Pet Friendly. Newly renovated with Central air (Slim line units)-Come have some fun in the sun at this Cape Cod Vacation home in Chatham! You will enjoy deeded access to the 'Little Beach flats'. Just moments away from the top attractions near our Chatham vacation rentals,...
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    Chatham, Cape Cod 02633
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 7 Quick View
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    Smoking allowed
    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $2450 No Off-Season Click for More Photos, Map, and Availability Calendar 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...
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, Sleeps 7
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    3 Bedrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $2,100 per week Click for More Photos, Map, and Availability Calendar This is a well maintained property located in a quiet area in W. Chatham. Spacious bedrooms, one with two double beds. Updated kitchen, with a skylight, opens to dining area &...
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    Chatham, Cape Cod 02633
    Rental Home - 3 Bedrooms, Sleeps 8
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