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Chatham Vacation Rentals

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    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    All 193 Rentals in Chatham
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    Captain's Haven1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Beautiful sunsets in Chatham!1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Cape Escape Chatham Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 55
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
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    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    14 Hallett Lane Chatham Cape Cod - Sand Simeon1 / 49
    (6)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 2017
    Wow! We were impressed from the moment we walked through the door. The home is quite large, very well appointed and was very clean. We met people there and the home was great...
    Reviewed May 12, 2017
    This home was perfect for our group! Great space to have the group all together but at the same time when rooms are spread out so the home doesn't feel crowded with large groups...
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    About this property
    Come stay at: Sand Simeon. Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home offering 6 bedroom 6.5 bathrooms. Bonus: Linens (bed sheets and bath towels) are complimentary with this home for the Peak Summer Season. This luxury home is pet friendly with a private pool,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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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
    • Wi-Fi
    • Air Conditioning
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    • Patio
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    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
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come Stay at: Chatterbox! Location! Location! Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Whether you enjoy cocktails on the traditional front porch, read a good book in the cozy sun room, eat outdoors on the mahogany deck, or take...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Forest Beach Cottage. This Cape Cod Vacation home rental in Chatham is just yards out of the back door to Forest Beach. Central AC for those hot summer nights. You can smell the salt water from this ranch-style home with four bedrooms, two baths, and an outstanding family room. (Small...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beach Chic Cape Escape! Chatham 5 Star Private-Newly Renovated 5m walk to beach1 / 55
    (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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    • Parking
    • 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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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Parking
    • DVD Player
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Cape Escape! Pet Friendly! Walk to Hardings Beach from this Chatham Vacation Rental Home. 4 Bedrooms, sleeps 8. Access to association dock and picnic area in Harding's Hills Association. AC units in 3 bedrooms and the main living area. There is cable and free WiFi too. Calling all...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Wi-Fi
    • Outdoor Dining Area
    • Waterfront
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 1, 2014
    We enjoyed our stay at the condo in Chatham. It was comfortable for 3 people. It was clean and the kitchen was well stocked. Kris gave us excellent directions and suggestions.
    Reviewed August 14, 2014
    Having coffee each morning on the deck of this adorable cottage was one the highlights of my stay in Chatham. The view is terrific - of a lovely harbor that is called Mill Pond...
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    About this property
    Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village.
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in a prime in-town location. 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 blocks to beautiful Lighthouse Beach. This desirable and newly renovated family compound built by a famous...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pet Friendly! Coastal, 3 bedroom (sleeps 8) home offering spacious open floor plan, refurbished kitchen, cathedral ceilings, hardwood floors, free WiFi, and central AC. Attractively furnished, impeccably maintained, and fully equipped. This 3 bedroom, 2 bath ranch-style vacation rental home is...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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    • 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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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at: Seashell Beach Cottage! Beach front vacation rental cottage in Chatham! Stay at this 2 bedroom cottage located right on the beach in Chatham, the best of Cape Cod. Beautiful views! Perfect for a relaxing getaway, this romantic cottage is just steps from the sand, Find your pathway...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Captains Row E Chatham Cape Cod - Captain's Row1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 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...
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    About this property
    Welcome to Captain's Row! Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a community pool & tennis court (Only 130 steps from your door!). Also...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On the Water! With Central Air and free WiFi, Pet Friendly too. Pet friendly for Dogs only-ask your rental specialist for details. This Cape Cod Vacation Rental home in North Chatham has expansive views of Pleasant Bay from both a lower and upper deck, both living areas, the dining room and the...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience 'Chatham Coastal Charm'. Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (.3). Sleeps 10! Don't miss this 'fan favorite' Cape Cod Vacation Rental home in Chatham with heated pool that is very...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 to The Oyster Bed! Enter the home through the front entry and head up the stairs to find...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    14 Capri Lane Chatham Cape Cod - The Cape House1 / 31
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2018
    This cape house was just a perfect size for my family and we loved being able to bring our dog! We have 7 adults and one 4 year old. There were just a few things - the grill...
    Reviewed June 3, 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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    About this property
    Welcome to The Cape House! Pet Friendly! (Dogs Only) Coastal, seaside home offering Central air has plenty of room for 3 couples or 2 families. Walk to beach and town! This Cape Cod Vacation Rental in Chatham has an open floor plan with 3 bedrooms on the main floor and a fully finished lower level...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend an idyllic vacation swimming, sunbathing, and riding bikes across Cape Cod at this three-bedroom Harwich home, a secluded, family-friendly retreat with a private deck, an outdoor fireplace, and easy access to picturesque beaches and towns. This tree-lined home sits equidistant from Chatham...
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    Location Information
    West Chatham, Chatham 02645
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    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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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    61 Eliphamets Lane Chatham Cape Cod - Milhaven1 / 38
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 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...
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    About this property
    WATERFRONT! Come stay at: Milhaven, This Cape Cod Vacation Rental is located in Chatham's Old Village and is right on Mill Pond. The Old Village is popular for its historic nature and architectural beauty. Witness beautiful sunrise and sunset views as you are directly on the waterfront. It is...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Rosa Rugosa! Walk to Hardings Beach- Central air - private! Ranch-style home with Central air-comfortable, easy living all on one floor! 3 Bedrooms, 2 baths, sleeps 6 with central air, free WiFi, and sunroom. Beautiful gardens, patio, yard, and an easy walk to Harding's Beach! Quiet...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Welcome to Long Camp in Chatham! Pet Friendly! Come and enjoy a cozy vacation rental cottage on Goose Pond in Chatham. Goose Pond is the largest pond in Chatham and has 38 acres of unspoiled fresh water that is perfect for swimming, canoeing and kayaking. Free Wifi too. ​​​​​​​Nestled on the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    201 Main Street Chatham Cape Cod - Sandpiper1 / 42
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Experience the Sandpiper! Pet Friendly! 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! BONUS: LINENS INCLUDED IN SEASON. Whether you are soaking in the hot tub on the private patio or enjoying an outdoor shower after you've come home from Lighthouse or...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to Tide After Tide! Pet Friendly! Private, Family Ranch-Style Riverbay home in Chatham for your Cape Cod Vacation! Located on a peaceful, residential, dead-end road. As you enter the through the front door you will find comfortable seating in the living room with a flat screen TV and free...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 bedroom, 3.5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. BONUS: Linens included !. Privately placed on just over a half acre of land in a peaceful setting, yet just a hop, skip and a jump away you can find Lighthouse beach! It's an easy walk into the village...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. Located in a residential area and convenient to the Cape Cod Bike trail, and the Chatham Airport and restaurant (Hanger B eatery). It has 3 ac units in main floor bedrooms and free WiFi...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    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). Spacious 3+ Bedrooms with 2 extra private bonus rooms...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Come stay at: Donnadune. Pet Friendly! (for dogs only) Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Steps onto the large deck lead you to the entryway of this Cape home. Welcome back in time to when life was more simple-take the time to stare straight...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    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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    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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Welcome to ChathamBeachCruiser! Relax in our 5 bedroom 4.5 bathroom 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...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    415 Main Street Chatham Cape Cod - Mis Behavin'1 / 38
    (1)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Reviewed October 1, 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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    Come Stay at: Mis Behavin! Pet Friendly (for dogs only, please)! Charming, fully renovated Sea Captain's home, located in downtown Chatham. Enter through the sun porch offering extra dining- directly into the gourmet kitchen with a granite counter breakfast bar and café table for a total seating...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Welcome to Cranberry View! Pet Friendly (dogs only please). Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Privacy abounds just off Main Street and the home even overlooks a working Cranberry Bog! Window AC units in Bedrooms...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    17 Palmer Drive Chatham Cape Cod - The Little Caper1 / 27
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed July 18, 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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    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. Just under a mile to town, this coastal Cape is located in a quiet, family neighborhood. The home offers open living with plenty of space to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    *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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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    About this property
    Enter through the sliders on the deck to the large open Living area. You will find an L shaped comfy couch where you can kick your feet up and read a good book while enjoying the beautiful views of Bucks Creek out to the Nantucket sound! Stroll over to the wet bar and prepare your favorite libation...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
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    Welcome to Lorna Dune! Pet Friendly! A 5,000 square foot luxury 5 bedroom (sleeps 12 with extra bonus room), 5.5 bath vacation rental home in beautiful North Chatham. Walk to beach, Central air, free WiFi, and a heated swimming pool. Coastal comfort & style abound in this spacious home. First...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    From the second you arrive you will be ready to relax and unwind as you enter into this tastefully appointed, spacious home. Straight ahead you will find the heart of the house - the fully equipped kitchen complete with your own wet bar. Mix up your favorite libation and step through the French...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Welcome to Kuck's Kove. Newly renovated 4 bedroom, 3.5 bath custom home in North Chatham sleeping 10! Sit back, relax and enjoy this newly furnished property for your vacation get a way. Central air, WiFi, extra large Chef's kitchen, Spacious family room and Living room -outside patio with gas...
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    North Chatham, Chatham 02650
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    About this property
    Welcome to Seahold! Stay at this updated Chatham Vacation Rental located on a residential cul-de-sac of newer homes, well maintained 3 bedroom (sleeping 10). The interior has recently been refreshed for your comfort and relaxation. Central air will keep you cool and free WiFi will keep you...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Private Contemporary Cape Set on a Hilltop1 / 19
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
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    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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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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