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Pet Friendly Holiday Rentals in Chatham, MA

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 36
    North Chatham
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    North Chatham
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    South Chatham
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 36
    North Chatham
    Studio, 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) Located just 0.2 miles from the beach, this is an ideal estate for multi-generational families or other large groups to spend time together... View all property information
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    North Chatham, Chatham 02650
    1 / 43
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Waterfront & Dog friendly! Sleeps 8! This newer Cape Cod Vacation Rental home in Chatham offers panoramic views and backyard access to beautiful Blue Pond and deeded access to White Pond, perfect for swimming, kayaking, canoeing and fishing. Peak Summer Weekly Rates:  last week of June until the... View all property information
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    Chatham, Cape Cod 02633
    1 / 53
    North Chatham
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    Experience "The Salty Dog". Luxury at its finest. This 4,000 square foot, pet friendly, waterfront 4 bedroom/4 bath home sleeps 10. You will find Central Air, WiFi, linens, and all amenities at this Chatham Vacation Rental Home, everything for a great Cape Cod Vacation! Peak Summer Weekly... View all property information
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    North Chatham, Chatham 02650
    1 / 21
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to: Salty Paws! 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. Wifi and AC included. A Complete renovation is taking place over the winter. Everything will be "all new"! Peak Summer... View all property information
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    Chatham, Cape Cod 02633
    1 / 19
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,300/week. 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 37
    5 of 5 bubbles (1) Excellent
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    Experience the Sandpiper! Pet Friendly! Nothing beats this luxury 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! Peak Summer Weekly Rates:  last week of June until the first week in September: $9,100 - $9,400/week Whether you are soaking in the hot tub on... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 9
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 35
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Welcome to: Endless Sunsets! Pet Friendly! Oceanfront, updated Cape Cod Vacation Rental home in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,700/week. Picture yourself at this quaint beach cottage with ocean views and casual living for your summer... View all property information
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    Chatham, Cape Cod 02633
    1 / 25
    Studio, 3 Bathrooms, Sleeps 9 | Quick View
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    Renovated Sea Captain's Home by Ryder's Cove, Pet Friendly Peak Summer Weekly Rates: $3,000 - $3,500 This home has 4 bedrooms and classic Cape Cod decor. All of the modern amenities are included: AC units in all bedrooms, WiFi, flat screen TV with digital cable, washer/dryer, and a completely... View all property information
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    Chatham, Cape Cod 02633
    1 / 33
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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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... View all property information
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    Chatham, Cape Cod 02633
    1 / 38
    West Chatham
    Studio, 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. A/C units. Wifi too. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2,600 Walk to Harding's Beach from this Cape Style home! Enter into... View all property information
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    West Chatham, Chatham 02669
    1 / 28
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    [~]This beautiful home with central a/c sleeps 8 and has the open and bright spaces of a contemporary classic. The first floor boasts floor-to-ceiling windows facing the deck which overlooks acres of private woods and the heated swimming pool. This gorgeous deck contains a new wicker L-shaped... View all property information
    Location Information
    Chatham, Cape Cod 2633
    1 / 14
    Studio, 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 sleep sofa and the full bath was recently... View all property information
    Location Information
    Chatham, Cape Cod 02659
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    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September:$2,000/week. 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 26
    Studio, 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 10
    Studio, 2 Bathrooms, Sleeps 11 | Quick View
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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... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 24
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to: Sandy Paws! Pet Friendly. Come have some fun in the sun at this Cape Cod Vacation home in Chatham! You will enjoy deeded access to the "Little Beach flats". A Complete renovation is taking place over the winter. Everything will be "all new"! Peak Summer Weekly Rates:  last week of June... View all property information
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    Chatham, Cape Cod 02633
    1 / 23
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    ID #MARSH4 Dog Friendly and Now with A/C and WIFI Internet! [~]This 3.5 bedroom and 2 full bath vacation home in Chatham with beautiful marsh views is just a half mile from HARDINGS BEACH and Oyster Pond River/ The Chatham Kayak Co. This home offers such amenities as a washer/dryer, 3 A/C units,... View all property information
    Location Information
    Chatham, Cape Cod 2633
    1 / 7
    Studio, 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 24
    Studio, 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 28
    Studio, 4 Bathrooms, Sleeps 13 | Quick View
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    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) This classic home is perched in the dunes of Chatham, just to the south of Chatham Light. This large home is ideal... View all property information
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    Chatham, Cape Cod 02633
    1 / 22
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    #603 - Lovers Holley Home: Lovely renovated home less than one mile from Chatham's famous downtown shopping and overlooking Lover's Lake - which is a walk around corner in a few minutes. All Chatham beaches are within two miles.  This home, located in the Great Hills Estates, provides a very... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 30
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Pet Friendly! Located in a prime in-town location. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,875-$3,975/week. 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... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 37
    4 of 5 bubbles (1) Very good
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    Come Stay at: Mis Behavin! Pet Friendly! Charming, fully renovated Sea Captain's home, located in downtown Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $5,000/week Enter through the sun porch offering extra dining- directly into the gourmet kitchen with a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    4 of 5 bubbles Reviewed 2 October 2014
    Our family of four (parents with our 20-something daughters) rented this nicely renovated historic home in a downtown location... just blocks from the ocean. We went to Chatham...
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    1 / 12
    Studio, 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 47
    5 of 5 bubbles (1) Excellent
    Studio, 7 Bathrooms, Sleeps 16 | Quick View
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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. Peak Summer Weekly Rates:  last week of June until the first week in September: $16,525/week. This luxury home is pet friendly with a private pool, central a/c,... View all property information
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    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 27 May 2015
    This house is great. Has all the appliances you could want. Different coffee options, 2 sets of large washers and dryers, 3 dishwashers, pool table, big screen TV, pool with...
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    1 / 20
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
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    This newly renovated, quaint and charming home is set in the heart of Chatham village. Enjoy the full benefit of being steps away from Main Street, the scenic beaches, and the ocean. There are 3 bedrooms/2 baths and plenty of private outdoor space including an outdoor shower and a fire pit.... View all property information
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    Chatham, Cape Cod 02633
    1 / 42
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    Pet Friendly! Welcome to this English Garden inspired 3 bedroom 3.5 bath Chatham Vacation home with lovely coastal touches. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,000 - $4,400/week. Offering Central air, Wifi and an open, airy floor plan~ you are sure to... View all property information
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    Chatham, Cape Cod 02633
    1 / 23
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    Pet Friendly! Private, Family Ranch-Style Riverbay home in Chatham for your Cape Cod Vacation! Located on a peaceful, residential, dead-end road. Peak Summer Weekly Rates:  last week of June until the first week in September: $1,800-$1,900 per week $1250 off season As you enter the through the... View all property information
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    Chatham, Cape Cod 02633
    1 / 33
    5 of 5 bubbles (1) Excellent
    Studio, 6 Bathrooms, Sleeps 20 | Quick View
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    Come Stay at: The Priscilla House! Pet Friendly! The Priscilla House is a lovely vacation rental home nestled on Main Street in the charming town of Chatham, Massachusetts on Cape Cod. Walk to town and Lighthouse beach! Sheets and Towels INCLUDED! Peak Summer Weekly Rates:  last week of June until... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 31 May 2016
    This house was perfect for my group of 6 families with six 13 year old boys and their siblings. Despite the large group, it was incredibly quiet, we didn't get into each other's...
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    1 / 33
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to: Endless Summer. Views-Views-Views! Pet Friendly Cape Cod Vacation Rental home with rooftop deck is just .2 to Ridgevale Beach. Peak Summer Weekly Rates:  (last week of June until the first week in September) $4,050/week Pet friendly! Enjoy water views from the main floor living areas... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    Chatham, Cape Cod 02659
    5 of 5 bubbles 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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    1 / 19
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    Pet Friendly! Classic Cape Cod Vacation Home Rental in Chatham near Schoolhouse Pond for freshwater swimming. Peak Summer Weekly Rates:  last week of June until the first week in September:$2,000- $2,100/week Located in a residential area and convenient to the Cape Cod Bike trail, and the Chatham... View all property information
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    Chatham, Cape Cod 02633
    1 / 26
    North Chatham
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly! Quintessential Cape Cod 5 Bedroom Chatham Vacation Rental home with beach access.  A/C units in bedrooms and main living area.  Wifi too. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,600/week. Welcome to North Chatham- Here you will find a... View all property information
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    North Chatham, Chatham 02650
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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. $1600 per week * $100 Handling... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    On the Water! With Central Air and Wireless Internet-Pet Friendly too. Peak Summer Weekly Rates:  last week of June until the first week in September: $6,500/week Pet friendly for Dogs only-ask your rental specialist for details. This Cape Cod Vacation Rental home in North Chatham has... View all property information
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    Chatham, Cape Cod 02650
    1 / 31
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pet Friendly.  Relax in this 3 bedroom, 2 bath Cape Cod Vacation home in Chatham that is convenient to downtown Chatham and beaches. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500/week. Privacy abounds just off Main Street and the home even overlooks a... View all property information
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    Chatham, Cape Cod 02633
    1 / 35
    4.5 of 5 bubbles (4) Very good
    Studio, 2 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Come Stay at: The Bluff House! Pet Friendly!! High atop Sears Point in Chatham sits a Classic, Quintessential, New England Bluff house from yesteryear overlooking the sparkling, blue sea. Peak Summer Weekly Rates:  last week of June until the first week in September:  $6,500/week. This spot is a... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 23 November 2016
    Our family rented the Bluff House the last week of July and had a lovely time.As boat owners we took advantage of the mooring and dingy that comes with the house. Days were spent...
    5 of 5 bubbles Reviewed 19 September 2016
    My family has rented The Bluff House for the past ten years and we can’t imagine summer anywhere else! The rooms are airy and light, with amazing views across Oyster Pond River...
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    1 / 13
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Chatham, Cape Cod 02650
    1 / 22
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come Stay at: The Crow's Nest! Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,400/week. With the shade from the pines, the spray of sea salt from the Nantucket Sound and the warm... View all property information
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    Chatham, Cape Cod 02633
    1 / 23
    North Chatham
    Studio, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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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... View all property information
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    North Chatham, Chatham 02650
    1 / 32
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    • Smoking allowed
    • x
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    Central Air and Pet Friendly! Updated 5 Bedroom Cape Cod Vacation Rental Family Home in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,500/week. Large family? No problem! Can't leave home without Fido? Bring your doggie... View all property information
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    Chatham, Cape Cod 02633
    1 / 5
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    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,... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh water ponds and just a short drive to Pleasant Bay! The property offers four comfortable bedrooms and two baths, sleeping up to 8. The first floor has a fully equipped kitchen, cozy... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    Super affordable 2 bedroom/1 bath cottage! Walk to three Chatham beaches! Pet Friendly! [~]This enchanting 2 bedroom/1 bath cottage sleeps 6 guests in a classic Cape within scenic walking distance to Scatteree Beach, Cotchpinicut Beach, and Cow Yard Landing, one of Chathams best kept secrets.... View all property information
    Location Information
    Chatham, Cape Cod 02650