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Pet Friendly Vacation Rentals in Chatham, MA

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    1 / 15
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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. $1800 per week in season plus $160 Cleaning Fee made payable to Miriam Tambarussi $60 Handling Fee, & $55 Vacation Rental Damage Fee... View all property information
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    Chatham, Cape Cod 02633
    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: $3,800 - $4,200/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 / 9
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    SWEET HOME Sweet two bedroom plus den home in South Chatham about 8/10ths of a mile to Forest Street Beach. Sleeps 4. One queen and two twins. The den has a sleep sofa. A/C units in each bedroom. One bath with tub and shower. Outside shower off deck.WiFi. Summer rate $1050 weekly. Cleaning Fee... View all property information
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    South Chatham, Chatham 02659
    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: $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 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Pet Friendly. Come have some fun in the sun at this Cape Cod Vacation cottage 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: $1,800/week. Stroll just a half mile up to Lighthouse Beach-it's also an... View all property information
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    Chatham, Cape Cod 02633
    1 / 37
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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/week Whether you are soaking in the hot tub on the private patio or enjoying an... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    4 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Our Pleasant Street home is a charming 3 bedroom, 2 bath year-round home which is located at 320 Pleasant Street in South Chatham and it can comfortably accommodate up to 8 people. It is only a 2 minute walk to Nantucket Sound, the warm water side of Cape Cod! There is no beach sticker required... View all property information
    Location Information
    Chatham, Cape Cod 02659
    4 of 5 stars Reviewed 2 November 2012
    Our family spent Columbus Day weekend at this property located within walking distance of two beaches and enjoyed it very much. The expanded Cape had comfortable room for eight of...
    3 of 5 stars Reviewed 2 July 2012
    I traveled with three friends to Cape Cod for a week. Two of us were pretty happy with the selected property, and the other two were a little disappointed. The house is located...
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    1 / 40
    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, perfect for kayaking, canoeing and fishing. Peak Summer Weekly Rates: last week of June until the first week in September: $3,500 - $4,200/week... View all property information
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    Chatham, Cape Cod 02633
    1 / 31
    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: $3,800/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
    1 / 37
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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: $4500-$5,000/week Enter through the sun porch offering extra dining- directly into the gourmet kitchen with a granite counter... View all property information
    Location Information
    Chatham, Cape Cod 02633
    4 of 5 stars 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 / 47
    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    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, linens, wifi and more. In... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars 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 / 10
    6 Bedrooms, 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 for walking and biking and a tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy yard is... View all property information
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    Chatham, Cape Cod 02633
    1 / 38
    5 of 5 stars (1) Excellent
    9 Bedrooms, 5 Bathrooms, Sleeps 20 | Quick View
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    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 the first week in September: $7,500... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars 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 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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
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    Chatham, Cape Cod 02633
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    You'll have beautiful views of Nantucket Sound 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 has a finished basement with a large flatscreen TV with surround sound, pool table,... View all property information
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    Chatham, Cape Cod 02659
    1 / 26
    3.5 of 5 stars (2) Average
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    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: $4500- $6,500/week. This spot is a boater's paradise! From... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 stars Reviewed 3 weeks ago
    We recently stayed at 30 Seabeach rd for our second year in a row. This house is an amazing property with very special memories for us. Not only did we get married in Chatham last...
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    1 / 17
    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
    Location Information
    Chatham, Cape Cod 02659
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    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    16 ELLIS FOUR DAY SPECIAL FOR THE FOURTH OF JULY 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... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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. This property rents for $1400 -... View all property information
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    Chatham, Cape Cod 02633
    1 / 34
    South Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Take in views from almost every room at this updated Cape Cod Vacation Rental Home in Chatham. Peak Summer Weekly Rates: last week of June until the first week in September: $5500-$6,000/week. Small Dogs accepted. This home sits high on a hill overlooking both the Nantucket sound and the tidal... View all property information
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    South Chatham, Chatham 02659
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Pet Friendly! Located in a prime in-town location. Book June 25-July 1, 2016 for $1,000. Peak Summer Weekly Rates: last week of June until the first week in September: $1,800-$2,000/week. This Cape Cod Vacation Rental Cottage complex is just steps to the Mill Pond (a saltwater inlet of Nantucket... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Panoramic views of Nantucket Sound and a pristine salt marsh await you from this 3 bedroom, 2.5 bathroom South Chatham home. The back deck offers a commanding view of the estuary and wildlife including osprey and egrets while a winding path leads to a secluded beach with warm water and exposed sand... View all property information
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    Chatham, Cape Cod 02659
    1 / 23
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    This ideally situated, spacious 5 bedroom, 3 bathroom classic antique home is just steps away from gorgeous Lighthouse Beach and just a short distance to downtown Chatham as well as the famous Mitchell River bridge where fishing is bountiful. Outside, you can enjoy the deck overlooking your own... View all property information
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    Chatham, Cape Cod 02633
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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) $3,950/week Pet friendly! Enjoy water views from the main floor living areas and the upstairs master bedroom... View all property information
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    Chatham, Cape Cod 02633
    1 / 36
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Pet Friendly! Refreshed 5 bedroom 2 bath Cape Cod Vacation Rental home in downtown Chatham! Peak Summer Weekly Rates: last week of June until the first week in September: $5,500/week Wonderful in-town Chatham oasis. Park your car and walk to all things downtown Chatham has to offer including band... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Well maintained two bedroom home that sleeps 4.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 / 36
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    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: $4,800 - $5,200/week Steps onto the large deck lead you to the entryway of this Cape home. Welcome back in time to... View all property information
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    North Chatham, Chatham 02650
    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Lounge on our beautiful beaches, experience great fishing or spoil yourself in our unique shops all while staying in this charming, remodeled and finely decorated home close to Red River and Pleasant Street Beaches. This home has 4 bedrooms and 3 full baths. There is an en-suite master bedroom with... View all property information
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    Chatham, Cape Cod 02659
    1 / 31
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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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: $3,200/week. Privacy abounds just off Main Street and the home even overlooks a working... View all property information
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    Chatham, Cape Cod 02633
    1 / 40
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Pet Friendly! Newer Colonial Style vacation rental home in Chatham offers 2+ bedrooms (sleeping 8) and 2.5 baths. Peak Summer Weekly Rates: last week of June until the first week in September: $1,600/week. Easy access to Goose Pond for swimming and kayaking. With over 2400 Square feet and 3 levels... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Our Cranberry Way home is a charming 2 bedroom, 2 bath (one new) year-round home which is located at 47 Cranberry Way in South Chatham and it can comfortably accommodate up to 6 people. It is only 0.6/mi. to Nantucket Sound, the warm water side of Cape Cod! It is a pet-friendly home (with an... View all property information
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    Chatham, Cape Cod 02659
    1 / 37
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    ​Pet Friendly! Updated 4 Bedroom home sleeps 10-walk to Harding's Beach with Deck-Outdoor shower- A/C units. Wifi too. Peak Summer Weekly Rates: (last week of June until the first week in September) $2,000-$2,500 Walk to Harding's Beach from this Cape Style home! Enter into the open dining room... View all property information
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    West Chatham, Chatham 02669
    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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: $3,500 - $3,700/week. Picture yourself at this quaint beach cottage with ocean views and casual living for your summer getaway. Kayak for your... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Porch
    • Air Conditioning
    • Washer
    Suitability
    • 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 SPECIAL : $1000 a night for a short stay - min 3 nights between Aug 14-19, 2016!! Pet friendly for Dogs only-ask your rental specialist... View all property information
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    Chatham, Cape Cod 02650
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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 summer sun, you are sure to have a... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Grill
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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. Peak Summer Weekly Rates: last week of June until the first week in September: $2,500/week. The first floor contains a large living room with flat... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Waterfront
    • Patio
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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 Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situated between Nantucket Sound and Oyster... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    $12,400/week Peak Season (July 2nd - September 3) $8,400/wk for the weeks of (6/25 and 9/3) $7,700/week Shoulder Season (6/18 and 9/10) $6,100/week Shoulder Season (6/11 and 9/17) $5,500/wk (before 6/11 and After 9/24) This beautifully refurbished Chatham rental house has a path that leads to a... 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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    • Washer
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Why pay the new Homeaway/VRBO surcharge? Book with confidence and save when you book direct with Pretty Picky. Water Views Near Chatham Light, Guest Apartment, Sleeps 11 (Linens Included) Pets Considered Peak Summer Weekly Rates: $8,000 - $8,700This classic home is perched in the dunes of Chatham,... View all property information
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    Chatham, Cape Cod 02633
    1 / 34
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Why pay the new Homeaway/VRBO surcharge? Book with confidence and save when you book direct with Pretty Picky. Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,600 - $6,500 (Pets Considered) Located in a premier Chatham Village location, this classic... View all property information
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    Chatham, Cape Cod 02633
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Internet Access
    • Grill
    • Hot Tub
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This Cape Cod home has it all! With deeded beach access, a private hot tub, and dog-friendly accommodations with plenty of room inside, this house is a fantastic place for your next vacation. Located in a somewhat secluded area in North Chatham, this home is just a half-mile from Bassing Harbor.... View all property information
    Location Information
    Chatham, Cape Cod 02650