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Pet Friendly Holiday Rentals in Chatham, MA

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    $419
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 15
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Internet Access
    • Outdoor Dining Area
    • DVD Player
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    • Satellite TV
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    • Wheelchair access
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    • x
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    About this property
    Freshly painted Cape Cod home tucked just off of Route 28 near the Chatham/Harwich line. Very convenient location with a quick walk to two great restaurants and .7 mile walk to Forest Beach, and Pleasant Street Beach. House includes an open living/dining area, a first floor master bedroom and... View all property information
    Location Information
    Chatham, Cape Cod 02659
    5 of 5 stars Reviewed 7 January 2015
    Our family of four (children ages 12 and 14) stayed here August 2014. The property was well maintained, neat, and provided everything we needed, including sheets and beach...
    4 of 5 stars Reviewed 27 August 2014
    Adorable, comfortable home. Rooms and closets very spacious. Clean, well maintained. Children, 13, 13 & 10 loved it! Would def' return! Paula
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    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    $1,816
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    • ?
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    • Elder access
    • x
    • ?
    About this property
    ID #MARSH4 Dog Friendly and Now with A/C and WIFI Internet! [~]This 3 bedroom and 2 full bath vacation home in Chatham is just a half mile from HARDINGS BEACH with beautiful marsh views. This home offers such amenities as a washer/dryer, 3 A/C units, dishwasher, cable TV, WIFI, and a gas BBQ... View all property information
    Location Information
    Chatham, Cape Cod
    1 / 15
    4 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $405
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    • Washer
    • Grill
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    • Satellite TV
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    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Pleasant Street home is a charming 3 bedroom, 2 bath year-round home which is located at 320 Pleasant Street in South Chatham and it can comfortably accommodate up to 8 people. It is only a 2 minute walk to Nantucket Sound, the warm water side of Cape Cod! There is no beach sticker required... View all property information
    Location Information
    Chatham, Cape Cod 02659
    4 of 5 stars Reviewed 2 November 2012
    Our family spent Columbus Day weekend at this property located within walking distance of two beaches and enjoyed it very much. The expanded Cape had comfortable room for eight of...
    3 of 5 stars Reviewed 3 July 2012
    I traveled with three friends to Cape Cod for a week. Two of us were pretty happy with the selected property, and the other two were a little disappointed. The house is located...
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    1 / 30
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    $629
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    • Washer
    • Satellite TV
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    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Charming, fully renovated Sea Captain's home, located in downtown Chatham. Enter through the cozy porch directly into the gourmet kitchen with a granite counter breakfast bar and café table for a total seating of 8. Down the hall there are 2 spacious living areas offering several couches (one being... View all property information
    Location Information
    Chatham, Cape Cod 02633
    4 of 5 stars Reviewed 2 October 2014
    Our family of four (parents with our 20-something daughters) rented this nicely renovated historic home in a downtown location... just blocks from the ocean. We went to Chatham...
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    1 / 22
    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
    From
    $2,061
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    • Washer
    • Private Outdoor...
    • Grill
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home 6 bedroom 6.5 bath luxury home that is pet friendly with private pool, central a/c, linens, wifi and more. In historic village of Chatham and .2 to Lighthouse beach. This restored and completely updated home has earned a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars Reviewed 27 May 2015
    This house is great. Has all the appliances you could want. Different coffee options, 2 sets of large washers and dryers, 3 dishwashers, pool table, big screen TV, pool with...
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $419
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    • Wi-Fi
    • Grill
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! Enjoy this Cape Cod Vacation Rental cottage in Chatham offering 3 bedrooms and 2 baths at the end of a small lane across from the ocean. The first floor contains a large living room with flat screen TV and Wireless Internet, combined kitchen/dining room, washer and dryer, full bath,... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 26
    2 of 5 stars (1) Poor
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    From
    $838
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    • Washer
    • Wi-Fi
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Pet Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. This spot is a boater's paradise! From kayaking to boating enthusiasts :There is a mooring available for your use (reserve ahead of time.... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    From
    $838
    / Night
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    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Porch
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    On the Water! With Central Air and Wireless Internet-Pet Friendly too (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 master... View all property information
    Location Information
    Chatham, Cape Cod 02650
    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $5,029
    / Week
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    • Washer
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Lounge on our beautiful beaches, experience great fishing or spoil yourself in our unique shops all while staying in this charming, remodeled and finely decorated home close to Red River and Pleasant Street Beaches. This home has 4 bedrooms and 3 full baths. There is an en-suite master bedroom with... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 42
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    $699
    / Night
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Terrace
    • Balcony
    • Washer
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! Welcome to this English Garden inspired 3 bedroom 3.5 bath Chatham Vacation home with lovely coastal touches. Offering Central air, Wifi and an open, airy floor plan~ you are sure to find this home the perfect spot to rest, relax and rejuvenate. Consider this your home away from home... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 29
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
    From
    $1,257
    / Night
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    • Washer
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $8,000 - $8,700This classic home is perched in the dunes of Chatham, just to the south of Chatham Light. This large home is ideal for larger groups looking for a perfect Chatham... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $419
    / Night
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    • Satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! Newer Cape Cod Vacation Rental Townhome with beautiful views of Perch Pond, just minutes to Chatham Village and Beaches. Luxury Rental includes: Central A/C, 3 levels of living space with flat screens on every level, granite counter tops and WIFI! Enter through the front door and to... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 37
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    From
    $699
    / Night
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    • Wi-Fi
    • Grill
    • Waterfront
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! 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 at the horizon- where the ocean and sky... View all property information
    Location Information
    North Chatham, Chatham 02650
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $2,375
    / Week
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    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    You'll have beautiful views of Nantucket Sound from this 2 bedroom, 1.5 bath traditional Chatham vacation rental only 4/10ths of a mile to Red River Beach and 6/10ths of a mile to Pleasant Street Beach. This home has a finished basement with a large flatscreen TV with surround sound, pool table,... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 8
    South Chatham
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $1,676
    / Week
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    • Air Conditioning
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    • Pet-friendly
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    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    The Wee Hoose is a cute doll house cottage in South Chatham. This cottage is only 4/10 mile to a Nantucket Sound beach and public tennis courts are just down the street. This one bedroom cottage has one full bath, one window a/c unit, cable TV (with NESN) with DVD, Wi-Fi, large backyard with picnic... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    From
    $3,493
    / Week
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    • Patio
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm summer sun, you are sure to have a relaxing escape to the Cape. From kayaking (2 included!) to boating enthusiasts this rental... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $454
    / Night
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    • Washer
    • Wi-Fi
    • DVD Player
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! 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 the Beautiful Lighthouse Beach. This desirable and newly renovated family compound built... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 40
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $1,362
    / Week
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Porch
    • Terrace
    • Grill
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Pet Friendly! Newer Colonial Style vacation rental home in Chatham offers 2+ bedrooms (sleeping 8) and 2.5 baths with easy access to Goose Pond for swimming and kayaking. With over 2400 Square feet and 3 levels of living space you will have plenty of space to rest and relax in. A/C units in the... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $559
    / Night
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ↵Pet Friendly. 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 St. and the home even overlooks a working Cranberry Bog! Window A/C units in Bedrooms and Wifi too. An open spacious floor plan will... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 31
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    From
    $1,180
    / Night
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    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Pet Friendly! Nothing beats this luxury 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! 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 Andrew Harding's Lane beach - you will... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars Reviewed 2 May 2014
    My Husband and I along with 3 other couples enjoyed a long weekend in this beautiful home. We thoroughly enjoyed the downstairs entertainment room with the pool table, movie...
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $244
    / Night
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This charming Cape Cod style cottage is a delight! It is a 2 bedroom, 2 bath home (one large new one) on a large lot with much privacy. It has A/C, hi-speed wireless internet,a new wide-screen HD TV, new carpeting throughout the house, is on a no-outlet street so it is safe for children and is... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $405
    / Night
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    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This charming Cape Cod style home is an attractively-furnished 6 room, 3 bedroom, 2 bath home that is only a 2 minute walk from the Pleasant Street Beach, for which a sticker is not required. It has a rooftop deck with a lovely view of Nantucket Sound and is only 3 miles from downtown Chatham with... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    From
    $419
    / Night
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    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Classic North Chatham Escape, Pet Friendly Peak Summer Weekly Rates: $3,000 - $3,500 This home has 4 bedrooms and classic Cape Cod decor. All of the modern amenities are included: AC units in all bedrooms, WiFi, flat screen TV with digital cable, washer/dryer, and a completely updated kitchen with... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 34
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    $838
    / Night
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    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,600 - $6,500 Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham vacation. Park your car in the driveway and leave it for the week! Walk... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 35
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $489
    / Night
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    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Waterfront, Dog friendly, WiFi, and Central A/C! This newer Cape Cod Vacation Rental home in Chatham offers panoramic views and backyard access to beautiful Blue Pond, perfect for kayaking, canoeing and fishing. Four doors down, take a right and you're enjoying deeded rights to a private,... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    From
    $3,493
    / Week
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    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spend your vacation in this newer 2+ bedroom, 2.5 bath Chatham rental home situated on a lovely country lane only 3/10ths of a mile to Pleasant Street Beach on Nantucket Sound. This home boasts nearly every possible amenity including central AC, washer, dryer, dishwasher, cable TV (includes sports... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $314
    / Night
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $384
    / Night
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly! Located in a prime in-town location this Cape Cod Vacation Rental Cottage complex offers deeded access to the Mill Pond (a saltwater inlet of Nantucket Sound) and is just a few blocks to the beautiful Lighthouse Beach in Chatham's Old Village. This desirable and newly renovated family... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $419
    / Night
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Patio
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet Friendly. Come have some fun in the sun at this Cape Cod Vacation cottage in Chatham! You will enjoy deeded access to the 'Little Beach flats' and stroll just a half mile up to Lighthouse Beach-it's also an easy bike ride into the village! The cottage offers a main floor where there is an open... View all property information
    Location Information
    Chatham, Cape Cod 02633