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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.
    29 Matching Rentals in ChathamView all 373 rentals
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    Chatham Escape 5 min Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 47
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!1 / 48
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    #601 - The Salty Seashell: Great Holiday Deal! Beautiful private Chatham home in great location with a deck, patio, grill & yard!  You will fall in love with this bright and cheery Cape! Wide planked Pine Hardwood floors in Living room and Dining room. Wide Galley Kitchen, fully equipped, including...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    ENCHANTING COTTAGE FOR 5 OR 6 CLOSE TO FOREST BEACH IN CHATHAM! PET FRIENDLY!1 / 16
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 22 August 2017
    Pet friendly, clean, and the beach is a walk away! All amenities available at the house: grill, beach toys, games, etc. We loved our stay!
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    $1625 ($100 less if not bringing a pet) Rate includes all charges - no hidden fees! NEW LISTING! AFFORDABLE DREAM BEACH HOUSE IN CHATHAM WITH LARGE FRONT AND BACK DECKS, ROOM FOR 6, AND ONLY STEPS TO FOREST BEACH! PET FRIENDLY! There is a dreamlike quality to this 3 bedroom/1 bath cottage just...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    This quaint Cape home is located just minutes away from Harding's Beach, a beautiful and popular spot to spend the day soaking in the sun and sea. Situated along Bucks Creek Marsh and just a stone's throw from the Oyster River, this 3-bedroom home is a perfect mix of seclusion and convenience. A...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Internet Access
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    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, 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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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Chatham Family Compound Sleeps 16 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 Located just 0.2 miles from the beach, this is an ideal estate for...
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    North Chatham, Chatham 02650
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    #602 - Port View Home1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 4 weeks ago
    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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    #602 Port View Home: Nantucket sound awaits you in this sweetie beach house. Pull in the driveway, look to the left ... All you see is OCEAN. Magnificent Nantucket Sound with white sandy beach just waiting on you to put down the beach blanket and take a dip! Port view home offers great living space...
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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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    • Grill
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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. $1650 per week * $100 Handling...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $7,500 - $8,700 Rents Saturday to Saturday during peak season Please click on the 'Virtual Tour' to see a 3D tour of the home This classic home is perched in the dunes of Chatham,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    #604 The Hideaway: Less than a mile to one of the best beaches in Chatham! Feel the warm sand between your toes at Cockle Cove beach, just .8 mile walk/bike ride. Downtown Chatham just minutes away. The Hideaway lives up to its name with being tucked away at the end of a private road, completely...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chatham CapeEscape! Beach Chic Vacation Rental 5 min walk to beach-very Private1 / 48
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 2016
    What a unique & wonderful house in Chatham!  John & Ruby are really superb hosts, very accommodating, making sure we were all set… to our delight, John even texted to let...
    Reviewed 3 May 2016
    Plusses:* Kitchen is fully equiped and the stove is big and of excellent quality.* Showers have a lot of power.* Good size house (big living room, separate dining room, big...
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    About this property
    Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are bright and nicely appointed with...
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    Chatham, Cape Cod 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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    Pet friendly
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    Smoking allowed
    About this property
    $1795 ($100 less if not bringing a pet) Rate include all charges - no hidden fees! 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...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in the heart of Chatham, close to all of the activities and attractions. This two-story 4BR/2BA classic Cape-style home is just one mile from Oyster Pond Beach. You’re also 1.5 miles from downtown Chatham, bustling with shops, bars, and restaurants. Spend time enjoying Mother Nature—nearby...
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    North Chatham, Chatham 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,900 - $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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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Terrace
    • Balcony
    • Grill
    • Housekeeping Included
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming ranch is great for two families. Home has 3 bedrooms plus a bunk room, 2 baths, and is wheelchair accessible. The expanded Master Bedroom, en suite and hallway bathrooms, and kitchen are all newly renovated. The living room and Master Bedroom have new wide-screen HD TVs, and the house...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    16 ELLIS Pet friendly home in Chatham sleeps 4. Two bedrooms one with a queen and bedroom two has a queen and a single bed. 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. FRIDAY arrival and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    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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    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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    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. There is a sun room off the living room with a full-size sleeper sofa and the full bath was recently...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    South Chatham Cape Cod Vacation Rental (1798)1 / 17
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Reviewed 5 weeks ago
    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, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This traditional two bedroom, one bathroom Cape Cod cottage is just .4 miles from popular Ridgevale Beach. This one floor cottage has an open living room and dining area with flat screen TV, small kitchen (no dishwasher), bathroom with shower stall, and two bedrooms, one with a full-size bed and...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    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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