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Pet Friendly Holiday Rentals in Chatham

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    88 Matching Rentals in ChathamView all 389 rentals
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    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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    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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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 64
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 25 September 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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    *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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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2,700 per week Off-Season: $1,700 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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    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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    About this property
    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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    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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    Reviewed 11 August 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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    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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    3 Bedrooms, Sleeps 6 Quick View
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    2019 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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    4 Bedrooms, Sleeps 8 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $2,350 per week Off-Season: $2,050 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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rate (Cleaning Fee Included): In-Season: $1575 per week ~ FRIDAY TO FRIDAY Click for More Photos, Map, and Availability Calendar Bright, cheerful home with a peek of Pleasant Bay from the back deck. Swimming and Kayaking in Pleasant Bay is right down the road at Jackknife Beach! This...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 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, Sleeps 4 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $1425 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar 'The Cottage on the Curve' is the perfect beach get-away! This charming two bedroom cottage, with many updates, is just minutes to kayaking or...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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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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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    This stunning rental home is a walker's dream! Walk to the ponds, bike trails, conservation area and town! Featuring 4,100 sq ft of luxury living, you and your guests will enjoy every moment of your time here. The vaulted ceiling great room with a gas fireplace is perfect for gathering together...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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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    4 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 - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 7 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $2375 per week No Off-Season Click for More Photos, Map, and Availability Calendar Centrally located, this lovely updated three bedroom home is a wonderful spot for your Chatham vacation! Only one mile from everything downtown Chatham has to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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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 sandy...
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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 7 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 7
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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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 to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 11
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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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    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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    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, 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2019 Rental Rates (Cleaning Fee Included): In-Season: $2650 per week Off-Season: $1800 per week Click for More Photos, Map, and Availability Calendar Ideally located less than a half mile from popular Chatham Lighthouse Beach, this meticulously maintained home is just a quick walk to the beach, and...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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, 2 Bathrooms, Sleeps 6 Quick View
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    Well maintained two bedroom home that sleeps 6. One queen and 2 twins with a pullout in the den. Located in scenic North Chatham. A five minute drive from downtown Chatham, Chatham Bars Inn, the Lighthouse, Chatham Seaside Links golf course and the baseball field which hosts the Cape Cod Baseball...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 2 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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    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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    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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    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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    South Chatham Cape Cod Vacation Rental (1798)1 / 18
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 18 September 2017
    We were traveling with older kids and it was great to have our bedroom on the 1st floor with a master bath - it worked out perfectly! Also, being close enough for them to walk...
    Reviewed 24 August 2016
    This was a well maintained and modern house, lots of efficient space and amenities. It's not your beach shack right on the water or walkup in town, but if you're a 50 something...
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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 only 3/10ths of a mile to Pleasant Street Beach on Nantucket Sound. The master bedroom with queen bed is located on the first floor. The second floor bedroom has a queen and a twin bed and...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    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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    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. Close to town, Oyster Pond, Chatham Anglers games, golf, and tennis courts. Enclosed outdoor shower and patio with outdoor dining- 4...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham Cape Cod Vacation Rental (7129)1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 23 August 2017
    We had a wonderful week. The location and views were perfect. The home itself was tastefully decorated and included every amenity. The beds were clean and comfortable. We loved...
    Reviewed 14 September 2016
    This is a fabulous location for a family vacation. Close to a lovely beach, rooms that are nicely laid out and appointed. All the comforts of home, without the hassles. A...
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    About this property
    Just steps away from Forest Beach, this 3 bedroom, 3 bath home boasts wonderful views of Nantucket Sound from inside and out. The first floor has a comfortably-furnished living area, den with queen sleep sofa and large flat-screen TV, kitchen and full bathroom. A spiral staircase leads to the two...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $3225 per week Off-Season: $2325 per week Click for More Photos, Map, and Availability Calendar Private, traditional style Cape house in the peaceful Sears Point area of Chatham. It has a lovely sun porch, a spacious living room and a lovely...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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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    Located in the heart of Chatham Village, this award-winning home has been completely renovated and designed to capture the true spirit of the Cape. It has maintained its historic feel without compromising the modern comforts. The first floor offers a living room, dining room, sunroom,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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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    201 Main Street Chatham Cape Cod - Sandpiper1 / 42
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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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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    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, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    2019 Rental Rate: $3725 per week, including cleaning fee Off Season ~$2475 per week, including the cleaning fee Click for More Photos, Map, and Availability Calendar Impeccably maintained four bedroom home, in a great central location! Downtown Chatham is a quick 5 minute drive, as well as the...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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