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Pet Friendly Vacation Rentals in Chatham

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    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    $212
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    1 / 9
    4.5 of 5 stars (4) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
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    $3,035
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    1 / 15
    4 of 5 stars (2) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Enquiry
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    1 / 15
    4 of 5 stars (3) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    1 / 26
    4 of 5 stars (1) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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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
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    4 of 5 stars Reviewed 1 October 2014
    Our family of four (parents with our 20-something daughters) rented this nicely renovated historic home in a downtown location... just blocks from the ocean. We went to Chatham...
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    $1,026
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    1 / 20
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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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... View all property information
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    $1,457
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    1 / 14
    3.5 of 5 stars (2) Average
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    ENJOY PEACE AND TRANQUILITY AND PET FRIENDLY AS WELL! Property has deeded path in the neighborhood that leads to shortcut to Lovers Lake. Path from property goes behind neighborhood properties and leads to Northgate Road to Lover's Lake. Perfect spot for kayaks, canoes and paddle boats. Get out... View all property information
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    3 of 5 stars Reviewed 17 August 2014
    Loved the house but not the property management. We also missed the air conditioner in the master suite half the time although we were told we wouldn't need it. The ad reads...
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    1 / 11
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Pet friendly home with central air Comfortable 4 bedroom cape on a quiet street in Riverbay Estates. Convenient to Schoolhouse Pond and Jackknife Cove beach on Pleasant Bay. This home has central air conditioning, an enclosed outside shower, and is PET FRIENDLY. This property rents for $1400 -... View all property information
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    $520
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    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Classic North Chatham Escape, Pet Friendly $3,300 PRIME SUMMER WEEKLY RATE 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 granite... View all property information
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    $273
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    1 / 15
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    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
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    $1,639
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    1 / 10
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    PERFECT GETAWAY THAT IS SO CLOSE TO THE BEACH AND PET FRIENDLY!!! This cozy, comfortable beach cottage is located in the Horne Cottage area and is a five minute walk to beautiful beach just south of Lighthouse Beach near Outermost Marina. Lighthouse Beach is also about a 10 minute walk from this... View all property information
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    From
    $364
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    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. It is located in a residential area and is convenient to the Cape Cod Bike trail, and the Chatham Airport and restaurant (Hanger B eatery). It has 3 a/c units and wifi too. Enter the front... View all property information
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    $607
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    1 / 2
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Chatham Village Classic, Behind Lighthouse $5,200 Prime Summer Weekly Rate This grand Chatham Village family home is located in Chatham, right near the Lighthouse.This vintage antique house has 5 bedrooms, and a premier village location.Walk 3-5 minutes down the road to Lighthouse Beach, or walk... View all property information
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    $1,336
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    1 / 7
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Pet friendly home in Chatham sleeps 5. Two bedrooms one with a queen and bedroom two has a queen and a single bed with a futone. Outdoor seating on the deck is spacious. Enclosed outside shower. One and a half baths. WiFi. A/C in the bedrooms. A short drive to Harding beach. Email... View all property information
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    $589
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    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
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    $3,035
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    1 / 16
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Spend your vacation in this newer 2+ bedroom 2.5 bath Chatham rental home situated on a lovely country lane 3/10ths of a mile to Pleasant Street beach on Nantucket Sound. This home boasts nearly every possible amenity including central air, washer/dryer, dishwasher, cable TV (includes NESN) with... View all property information
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    1 / 26
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    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
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    $3,339
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    1 / 10
    6 Bedrooms / 2 Bathrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the 'loop' just around the bend from Stage Harbor. Wonderful area for walking and biking and a tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy yard is... View all property information
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    $1,518
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    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    241 Training Field Road Charming and updated 3 bedroom air conditioned ranch style home just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1800 per week in season plus $160 Cleaning Fee, $60 Handling Fee, made outto Bruce Court & $55 Vacation Rental Damage Fee. To reserve this home,... View all property information
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    From
    $1,791
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    1 / 20
    6 Bedrooms / 7 Bathrooms / Sleeps 16
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    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
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    $304
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    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
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    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
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    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    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
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    $728
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    1 / 24
    6 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Make Enquiry
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Pet Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house 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) and easy access down... View all property information
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    About this property
    Our Cranberry Way home is a charming 2 bedroom, 2 bath (one new) year-round home which is located at 47 Cranberry Way in South Chatham and it can comfortably accommodate up to 6 people. It is only 0.6/mi. to Nantucket Sound, the warm water side of Cape Cod! It is a pet-friendly home (with an... View all property information
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    1 / 34
    5 Bedrooms / 4 Bathrooms / Sleeps 13
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Water Views Near Chatham Light, Guest Apartment$7,900 PRIME SUMMER WEEKLY RATE Book July 4th Week -- Stay an Extra Night at 50% off the nightly rate! This 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... View all property information
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    $334
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    1 / 19
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
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    • Air Conditioning
    • Grill
    • Satellite TV
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    $395
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    1 / 28
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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... View all property information
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    $395
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    1 / 20
    South Chatham
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Pet Friendly. Seaside Cape Cod Vacation Rental vacation home in Chatham with stunning views of the ocean, accommodates 6-8 guests. Relax on the living area and enjoy the flat screen TV. There is an A/C unit on the main floor to keep you cool and WIFI to keep you connected. Just around the corner is... View all property information
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    $3,399
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    1 / 25
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    68 Summer Hill Lane CHATHAM Charming Large Post and Beam Cape Style home privately nestled on a quiet lane. 4 bedrooms and 3 bathrooms. Open kitchen/dining/living room floor plan. Spacious Great Room with cathedral ceilings, central A/C, master suite away from main living area. Private courtyard,... View all property information
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    1 / 23
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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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
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    $401
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    1 / 21
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Pet Friendly! Cape Cod Luxury vacation condo in the heart of Chatham Village! Head up the stairs over the Chatham Beach Dog to find a lovely deck with café table and gas grill. Open the door to your little piece of heaven: the open floor plan boasts a gourmet kitchen, including a breakfast bar for... View all property information
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    $2,550
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    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Charming cape-style pet friendly home close to all that the village has to offer. PET FRIENDLY Charming cape-style home close to all that the village has to offer. Walk to town, Oyster Pond, Chatham Anglers games, golf, and tennis courts. This home is pet friendly. $2100/week in Season with a... View all property information
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    From
    $13,082
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    1 / 42
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Pet Friendly, waterfront estate. Private dock on Crow's Pond leading out to Pleasant Bay with beach area and use of mooring with rowboat. Find your little piece of heaven in this 4 bedroom, Cape Cod Vacation Rental home in Chatham with spacious, manicured grounds, great outdoor spaces, Central air... View all property information
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    $304
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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    5 Bedrooms / 4 Bathrooms / Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Classic Chatham Charm -- Walk to Beach & Town! $5600 PRIME SUMMER WEEKLY RATE 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 to everything: downtown... View all property information
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    From
    $2,185
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    251 Joshua Jethro PET FRIENDLY Wonderful three bedroom three bath Cape-style home in the Riverbay community of Chatham with central A/C. The kitchen and all three bathrooms have been recently renovated and the first floor bathroom includes a whirlpool jet bathtub. The first floor bedroom has a... View all property information
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