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Pet Friendly Holiday Rentals in Chatham

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    Travellers to Chatham are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    96 Matching Rentals in ChathamView all 456 rentals
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    Beach Chic Cape Escape! Chatham 5 Star Private-Newly Renovated 5m walk to beach1 / 54
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Cape Escape Chatham Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 53
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    #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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    Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!1 / 29
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 30 September 2017
    Very nice Chatham, Cape Cod home with great views, and not too far from town. A comfortable home that I would rent again, and the managment company was good about staying in...
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    Experience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the ocean and Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situated between Nantucket Sound and...
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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 10 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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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, 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, 1 Bathroom, Sleeps 6
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,050 per week Off-Season: $1,750 per week Click for More Photos, Map, and Availability Calendar Spacious 4 BR home on quiet street near Cockle Cove Beach. Lots of living space in this private and centrally located home. Minutes from bike trail...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    This 3.5 bedroom and 2 full bath dog-friendly vacation home in Chatham with beautiful marsh views is just a half mile from Hardings Beach and Oyster Pond River. This home offers such amenities as a washer/dryer, 3 A/C units, dishwasher, cable TV, WIFI, and a gas BBQ grill. The first bedroom,...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Vacation Spot Right up the Road from Pleasant Street Beach in South Chatham! Well appointed and comfortable, this home is convenient to all the area has to offer. Enjoy grilling on the deck in the private backyard after a day enjoying summer on Cape Cod! Four bedrooms and 2 1/2 bathrooms...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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, Sleeps 10 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2825 per week Off-Season: $2025 per week Click for More Photos, Map, and Availability Calendar Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean from large deck. Short walk to Cow Yard...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,600 per week Off-Season: $1,600 per week Click for More Photos, Map, and Availability Calendar Wonderful, light and bright summer home located just steps from Taylor's Pond, the Eel River and the warm waters of the Nantucket Sound. Even...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Friday to Friday Rental This cottage is converted out of an a barn built in 1792. The upstairs bedroom has a full bed and the downstairs bedroom has a day bed (2 twin beds). This cottage is not for everyone. The entrance to the upstairs bedroom is steep and 18' wide. You can see it next to the...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 7 Quick View
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    2018 Rental Rate (Cleaning Fee Included): In-Season: $2375 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT Comfortable year-round home in a quiet neighborhood near downtown Chatham. It features two living areas, plus a glassed-in sun porch....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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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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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,975 per week Off-Season: $1,425 per week Click for More Photos, Map, and Availability Calendar Enjoy the simple life in this classic, Chatham cottage. Located in the popular Hardings Hills neighborhood, a quick walk down to Hardings Beach!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rate (Cleaning Fee Included): In-Season: $1550 per week ~ No Off-Season Click for More Photos, Map, and Availability Calendar Enjoy your Chatham summer vacation in this light and bright vacation home. Located on a quiet side street, on the way to Ridgevale Beach, one of Chatham's most...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,310 - $6,750 (Pets Considered)  Rents Saturday to Saturday during peak season Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 11 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $5350 per week (linens included) Off-Season: $4400 per week (6/23 to 6/30 & 8/25 to 9/1) (linens included) Click for More Photos, Map, and Availability Calendar Gorgeous home in secluded North Chatham neighborhood. The home features hardwood...
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    North Chatham, Chatham 02650
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    14 Capri Lane Chatham Cape Cod - The Cape House1 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 3 June 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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    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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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    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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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Enjoy Family Tides, this pet friendly, updated, 4 bedroom home sleeps 10. Walk to Harding's Beach with deck and outdoor shower. AC units. Free WiFi too.  Walk to Harding's Beach from this Cape Style home! Enter into the open dining room with seating for 6-8 + 2 at the breakfast bar. One step down...
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    West Chatham, Chatham 02669
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Pretty, shabby chic, sunny cottage and barn on private two acres of land down quiet country road. Brand new six person hot tub on deck, in time for fall or winter rental. The grounds are naturally landscaped, not manicured, no chemicals used. Enjoy the serenity of the undisturbed woods, open floor...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    This perfectly situated Chatham rental is welcoming to you and your four legged friends. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to town on sidewalks and enjoy the amazing shops and restaurants. Head to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2018 Rental Rate: $3225 per week, including cleaning fee Off Season ~$2225 per week, including the cleaning fee Click for More Photos, Map, and Availability Calendar Well Maintained, comfortable 4 BR, 2.5 BA rental home in a great central location, a quick drive to town or the beach! A great set up...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Located in the heart of Chatham Village with its many delightful shops, galleries, and restaurants this 2 bedroom home is close to everything Chatham has to offer. Enjoy a short stroll to Lighthouse Beach, the Chatham Fish Pier, tranquil Mill Pond or the Orpheum Theatre. The first floor offers a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 12 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2225 per week Off-Season: $1525 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT Charming home located in terrific central area of North Chatham. Walk to Ryder's Cove boatyard. Beautifully...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 12
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Chatham Family Compound Sleeps 16   August 11 - 18 Reduced to $9,300! Walk to Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900  Rents Saturday - Saturday during peak season   Please click on the 'Virtual Tour' to see a 3D tour of the home Welcome to sublime summer living at the...
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    North Chatham, Chatham 02650
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, Sleeps 4 Quick View
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    2018 Rental Rate: $1325 per week, including the cleaning fee ~~~ Off-Season: $1075 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming cottage in the woods and only 2 minutes to Oyster River Public Boat Landing. Small screened-in porch attached. A great vacation...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2600 per week Off-Season: $1700 per week Click for More Photos, Map, and Availability Calendar Pet Friendly! Spacious four bedroom home in quiet neighborhood near town. Path to a small private beach on Lovers Lake too! Plenty of space in the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    PROPERTY OVERVIEW Located just steps from family-friendly Ridgevale Beach, this charming 2BR/1.5BA cottage offers a quintessential Chatham vacation. The walk to the coast is short and the shops and restaurants of downtown are just a quick drive away! Spend your days at the picturesque beach...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 7 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $3,175 per week No Off-Season Click for More Photos, Map, and Availability Calendar Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,900 per week Click for More Photos, Map, and Availability Calendar Adorable beach cottage located less than 1/2 of a mile to the peaceful shoreline of Forest Beach and a 1/2 mile stroll to 2 great dining establishments, Pieces & The Talkative...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Chatham Village Classic, Behind Lighthouse (Pets Considered)  Peak Summer Rates: $5,300 - $5,500 Rents Saturday to Saturday during peak season 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Enjoy this lovely Chatham vacation rental located in desirable North Chatham near, gorgeous beaches, restaurants & Chatham Village. Here you can enjoy everything Chatham has to offer, from Chatham baseball games, the village area with restaurants & shops, Lighthouse beach & more! Gorgeous...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    Come Stay at: The Crow's Nest! Dog 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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks - $2,000 Rents Saturday - Saturday during peak season Please note:  This property is part of a larger estate, and is only available to rent individually in the months outside of July and August...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    14 Hallett Lane Chatham Cape Cod - Sand Simeon1 / 48
    (6)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 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 12 May 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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    241 Training Field Road PET FRIENDLY Charming and updated 3 bedroom air conditioned ranch style home, just 1 mile from beautiful Pleasant Bay at Jacknife Point Beach. $1900 per week in season * $160 Cleaning Fee * $100 Handling Fee * $55 Damage Insurance OR $500 Security Deposit Please contact...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2250 per week Off-Season: $1650 per week Click for More Photos, Map, and Availability Calendar 2018 Rental Rate: $2250 per week, including the cleaning fee Off-Season: $1650 per week, including the cleaning fee Ideally located less than a half...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful views of Nantucket Sound abound 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 boasts multiple living areas including the living room, which has recently been upgraded...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 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 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This traditional two bedroom, one bathroom Cape Cod cottage is just .4 miles from popular Ridgevale Beach. This one floor cottage has open dining and living rooms (new couch and chair coming for 2018) with flat screen TV, small kitchen with new stove for 2018, bathroom with shower stall, and two...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    This 5 bedroom, 3 bath Chatham rental home has incredible water views of Taylor's Pond. The home is surrounded by oak trees creating a very private setting. There is a spacious deck with dining table for dining alfresco. A path offers direct access to Taylor's Pond for kayaking, canoeing or...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    New to market. 3 bedroom (plus separate sleeping porch) 1 1/2 bath, outdoor shower. Lots of parking with room for a trailered boat. 1930s Chatham farmhouse, with all the charm. If you have a boat, or like to paddleboard and kayak, the house is .2 miles from beautiful Barn Hill landing with its...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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