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Chatham Pet Friendly Vacation Rentals

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    1 / 47
    5 of 5 bubbles (20) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    South Chatham, Chatham 02659
    1 / 45
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    South Chatham, Chatham 02659
    1 / 22
    3 Bedrooms, 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
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    Chatham, Cape Cod 02633
    1 / 24
    North Chatham
    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... View all property information
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    North Chatham, Chatham 02650
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Terrace
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    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... View all property information
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    Chatham, Cape Cod 02633
    1 / 48
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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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 / 43
    3 Bedrooms, 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
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    1 / 52
    5 of 5 bubbles (2) Excellent
    North Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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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
    5 of 5 bubbles Reviewed 4 weeks ago
    We were looking for a pet friendly place to get away for a long overdue vacation and the Salty Dog fit the bill quite nicely. The pictures cannot capture the beauty of the...
    5 of 5 bubbles Reviewed 3 April 2017
    This beautifully furnished, casually comfortable rental feels like home! In an idyllic setting on the water, close to beaches and town, we are in love with the property! Plenty...
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    1 / 42
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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 / 47
    5 of 5 bubbles (6) Excellent
    6 Bedrooms, 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: $11,000- $16,525/week. This luxury home is pet friendly with a private pool, central... View all property information
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    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 2 weeks ago
    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...
    5 of 5 bubbles Reviewed 2 weeks ago
    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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    1 / 38
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 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
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    Chatham, Cape Cod 02633
    1 / 34
    4.5 of 5 bubbles (2) Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Central Air and Pet Friendly! Totally 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: $3,600- $4,200/week. Large family? No problem! Can't leave home without Fido?... View all property information
    Location Information
    Chatham, Cape Cod 02633
    4 of 5 bubbles Reviewed 17 April 2017
    With family and friends out for our daughter's wedding in Boston last September we wanted a place immediately afterward for an extended reunion. It was all made possible on a...
    5 of 5 bubbles Reviewed 14 April 2017
    My boyfriend and I rented this home with two other couples for a relaxing getaway in our favorite spot on Cape Cod - Chatham! The house was so beautiful and newly renovated...
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    1 / 29
    North Chatham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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: $3500- $4,600/week. Welcome to North Chatham- Here you will find a... View all property information
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    North Chatham, Chatham 02650
    1 / 23
    3 Bedrooms, 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: $1,650-$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 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to: Salty Paws! Pet friendly! Newly renovated- 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 Central AC included (slimline Units). Peak Summer Weekly Rates:  last week of June until the first... View all property information
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    Chatham, Cape Cod 02633
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    1 / 33
    3 Bedrooms, 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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    4 Bedrooms, 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 / 38
    West Chatham
    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. A/C units. Wifi too. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2000-$2,600 Walk to Harding's Beach from this Cape Style home!... View all property information
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    West Chatham, Chatham 02669
    1 / 19
    2 Bedrooms, 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: $2000-$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... View all property information
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    Chatham, Cape Cod 02633
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Price $1,400 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
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    Chatham, Cape Cod 2633
    1 / 19
    1 Bedroom, 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
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 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: $3,400-$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
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    Chatham, Cape Cod 02633
    1 / 35
    4.5 of 5 bubbles (4) Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    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. SPECIAL- Week of... View all property information
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    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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Chatham, Cape Cod 02650
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to: Sandy Paws! Pet Friendly. Newly renovated-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". Peak Summer Weekly Rates:  last week of June until the first week in September: $3000 per week Just moments away... View all property information
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    Chatham, Cape Cod 02633
    1 / 37
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 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
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    Chatham, Cape Cod 02633
    4 of 5 bubbles Reviewed 1 October 2014
    Our family of four (parents with our 20-something daughters) rented this nicely renovated historic home in a downtown location... just blocks from the ocean. We went to Chatham...
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    1 / 36
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Come stay at: Donnadune. Pet Friendly! Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Peak Summer Weekly Rates:  last week of June until the first week in September: $5,200 - $5,500/week Steps onto the large deck lead you to the entryway of this Cape home.... View all property information
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    North Chatham, Chatham 02650
    1 / 45
    5 of 5 bubbles (1) Excellent
    9 Bedrooms, 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
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    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 / 12
    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... View all property information
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    Chatham, Cape Cod 02633
    1 / 22
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    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
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    5 Bedrooms, 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 / 33
    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: $5,900 - $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
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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 sleep sofa and the full bath was recently... View all property information
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    Chatham, Cape Cod 02659
    1 / 26
    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... View all property information
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    Chatham, Cape Cod 02633
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    2 Bedrooms, 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
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    North Chatham
    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... View all property information
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    North Chatham, Chatham 02650
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 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
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    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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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Price Range $1100 - $1300. BOOK BEFORE JUNE FOR $1100 WEEKLY! THAT'S $200 OFF THE REGULAR RATE! 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... View all property information
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    Chatham, Cape Cod 02659
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    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Totally Renovated North Chatham Retreat Easy Access to Ryder's Cove, Linens Included (Beds Made), Pets Considered Monthly Rentals Available Peak Summer Weekly Rates: $2,950 - $3,200 (Rents Saturday to Saturday during peak season) This newly remodeled home is set in a private, upscale North Chatham... View all property information
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    North Chatham, Chatham 02650
    1 / 25
    4 Bedrooms, 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 / 36
    North Chatham
    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) 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 / 24
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Spacious Modern Six Bedroom Chatham Home, Sleeps 14+, Pets Considered (Linens Included) Brand new listing for 2017! Peak Summer Weekly Rates: $6,490-$7,490 (Rents Saturday to Saturday during peak season) Welcome to Leeward Mark!  Located just off Chatham's famous "Loop", this modern 6 bedroom home... View all property information
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    Chatham, Cape Cod 02633
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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... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    Price Range $3650 - $4150 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... View all property information
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    Chatham, Cape Cod 2633
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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,... View all property information
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    Chatham, Cape Cod 02633