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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.
    1 / 16
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 15
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    1 / 11
    4 of 5 bubbles (1) Very good
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This light and bright 3 bedroom, 2 bath ranch is located directly across from White Pond, a large fresh water pond great for swimming, paddle boarding, kayaking or fishing. It is also adjacent to the Old Colony Rail Trail (bike path) for easy access to downtown Chatham or to the Cape Cod Rail Trail... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Situated at the end of a cul-de-sac in a wonderful neighborhood this Chatham home has a very private backyard which abuts conservation land. This 4 bedroom, 2 bath home is also just a half-mile from Nantucket Sound Beaches. Amenities include central AC, washer, dryer, dishwasher, cable TV (includes... View all property information
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    Chatham, Cape Cod 02659
    1 / 6
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Cape cod home on the shores of South Chatham. The main floor constists of an eat in kitchen, living room / dining room with three picture windows, a brick fireplace, a four window reading room facing the ocean, and a full bathroom with an accessable shower. The upstairs sleeping area has a master... View all property information
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    South Chatham, Chatham 02659
    1 / 9
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Enjoy your summer vacation in this charming bright, contemporary home just 1/2 of a mile to Pleasant Street and Red River Beaches. This 3 bedroom, 2 bath home was fully renovated in 2007 including bathrooms, kitchen and flooring. Enjoy furnished multi-level decks with a gas grill, nice yard and an... View all property information
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    Chatham, Cape Cod 02659
    1 / 19
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This recently renovated and expanded 3 bedroom, 2 bathroom home offers fantastic sea breezes and views of Nantucket Sound. The living room and queen bedroom also have views of the water. The new kitchen is bright and functional with granite countertops and a large separate dining area. The new... View all property information
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    Chatham, Cape Cod 02659
    1 / 26
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    About this property
    Enjoy easy resort style living in this newer Cape Cod Vacation Rental home in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,600/week. This home is in its own residential sub division and is close to beaches, restaurants, downtown and includes a... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
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    About this property
    Large home sleeps 12 in Chatham Wonderful vacation home on one acre of land. Very private backyard in Charming Chatham. Boasts all of the amenities, newly rennovated kitchen and bathrooms, air conditioning units in all bedrooms and living areas. Close to town, School House Lake, Beaches, and Cape... View all property information
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    Chatham, Cape Cod 02633
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    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beachfront townhome! Sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor and Little Beach. Bike to town or the Monomoy Wildlife Refuge.​ Central AC and WiFi too. Peak Summer Weekly Rates:  last week of June until the first week in... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
    5 of 5 bubbles (4) Excellent
    Studio, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    This adorable, updated and meticulously maintained 2 bedroom, 1 bathroom quintessential Chatham vacation cottage has views of Nantucket Sound. This rental is only 2/10ths of a mile to Forest Beach and Pleasant Street Beach. (The rental does not included access to the beach shown in the photos which... View all property information
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    Chatham, Cape Cod 02659
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Pet-friendly
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    About this property
    Enjoy the downtown location of this Cape Cod Vacation Rental Home in the village of Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,950/week. Convenient to Chatham shops, restaurants, new Orpheum movie theatre and Oyster Pond. Families love the proximity... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This 4 bedroom, 2.5 bathroom house is within walking distance to downtown Chatham with some of the best restaurants and shopping that Cape Cod has to offer. The living room offers plenty of new, comfortable seating and the kitchen, with granite countertops and stainless appliances, is fully stocked... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stay in the heart of Chatham Village in this well-maintained 3 bedroom 1.5 bathroom home. Situated in a quiet neighborhood only 4/10ths of a mile from the shops and restaurants on Main Street, baseball field, playground and the Fish Pier. This traditional Cape home features a queen bedroom on the... View all property information
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    Chatham, Cape Cod 02633
    1 / 7
    North Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
    • Private Garden
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    About this property
    Spacious four bedroom ranch in Riverbay, a quiet neighborhood that is great for walking, and is only 1 mile from the calm waters of Jackknife Beach on Pleasant Bay! The house is cheerfully decorated with bright colors and upscale furnishings. The finished basement provides extra space for playing... View all property information
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    North Chatham, Chatham 02633
    1 / 23
    4 Bedrooms, 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 / 17
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    195 Cedar Street Chatham - ID# 106000 Location, location, location! Only a half mile to the beach at Oyster Pond and 3/4 mile to the Village of Chatham. Located on the Chatham Loop, this is a wonderful newly renovated home including a fabulous new kitchen with sunny breakfast nook. Living room,... View all property information
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    Chatham, Cape Cod 02633
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Waterfront
    • Washer
    • Internet Access
    • Patio
    • Parking
    • Satellite TV
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    • Child-friendly
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    About this property
    338 Seapine Road CHATHAM, ID# 104736 Waterfront 3 bedroom home overlooking Bassing Harbor and Fox Hill with the outer beach beyond. Located on a cul de sac near Eastward Ho! Country Club in North Chatham, the home is a classic Cape in style. Water access for kayaking in Pleasant Bay and beyond.... View all property information
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    Chatham, Cape Cod 02633
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    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 A/C included. A Complete renovation is taking place over the winter. Everything will be "all new"! Peak Summer... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 19
    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    $7,200/week Peak Season (July 22 - August 18) $6,800/week On Season (7/1, 7/8, 7/15, 8/19 and 8/26) $5,000/week Off Season (week of June 24 and Sept 2) $4,300/week Off Season (week of June 17 and Sept 9) $3,600/week Off Season (before June 16 and after Sept 15) Spectacular 3+ bedroom, 3.5 bath home... View all property information
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    Chatham, Cape Cod 02633
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
    About this property
    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 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Satellite TV
    • Balcony
    • Grill
    • Parking
    • Internet Access
    • Air Conditioning
    • Patio
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    About this property
    3 Bedrooms (Master w/ Ensuite), 3 Bathrooms, Sleeps 8 - Sofa Sleeps 2 Addl Newly renovated (March 2016), quaint and charming in the heart of Chatham Village Center. Enjoy the full benefit of being steps away from the hustle and bustle of Main Street in one direction, or the scenic beaches and... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come stay in this lovely, light, bright and open 2+ bedroom, 2.5 bath home with newly installed wall mounted AC unit on the first floor and window units in each bedroom. The deck overlooks a very private backyard with enclosed outdoor shower and charcoal grill. This rental is convenient to... View all property information
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    Chatham, Cape Cod 02633
    1 / 23
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This beautiful, newer 4 bedroom, 3 bath custom home has an expansive deck and custom built patio area with plenty of outdoor seating, a fire pit and both gas and charcoal grills. It is only 6/10ths of a mile to Forest Beach and even closer to a public tennis court and basketball hoop. The interior... View all property information
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    Chatham, Cape Cod 02659
    1 / 17
    Studio, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This renovated antique 3 bedroom, 1 full bathroom Chatham home is located in a lovely neighborhood in Chatham Village. It is only 7/10ths of a mile to the shops and restaurants on Main Street in downtown Chatham and even closer (.25 mi) to the Chatham Fish Pier, Chatham Bars Inn and Claflin Landing... View all property information
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    Chatham, Cape Cod 02633
    1 / 21
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, children's books and videos,... View all property information
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    South Chatham, Chatham 02659
    1 / 22
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    About this property
    Paradise Found at this special retreat in this Cape Cod Vacation home Rental in Chatham called the Heron's Nest! Peak Summer Weekly Rates:  last week of June until the first week in September: $4,600/week. This spacious , Four Bedroom, 3 bath luxury Chatham Rental will surely delight you in every... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
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    About this property
    2017 Rental Rate: $2175 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning fee Wonderful two bedroom summer rental, just steps to the center of Chatham! Filled with comfortable upscale furnishings, it offers plenty of living space and a great location near the... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is a terrific, newer, bright 3 bedroom, 2 full bathroom Chatham rental home situated only 2/10ths of a mile from popular Ridgevale Beach. This home is nicely decorated with newer, tasteful furnishings. Amenities include central AC, washer, dryer, dishwasher, cable TV (includes sports and... View all property information
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    Chatham, Cape Cod 02633
    1 / 17
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • ?
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    • x
    About this property
    2017 Rental Rate: $4150 per week including the cleaning fee ~~ Off-Season: $3175 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great family rental home, within walking distance to the warm waters of kid-friendly Hardings Beach! There is sleeping for 10 people,... 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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    • Wi-Fi
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    • Grill
    • Terrace
    • Balcony
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    • Pet-friendly
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    • x
    About this property
    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 / 12
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    04/01/17 - 06/24/17 $1,700 06/24/17 - 07/01/17 $2,100 07/01/17 - 08/26/17 $2,900 08/26/17 - 09/02/17 $2,000 09/02/17 - 10/28/17 $1,700 Enjoy the convenient location of this 3 bedroom, 2 full bathroom classic Cape style Chatham rental home close to downtown Chatham, Oyster Pond, and Clafflin... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This Chatham rental home has 3 bedrooms and 1.5 baths. It's situated in a private setting, abutting conservation and convenient to both downtown Chatham and beaches. This property is only 1/2 mile to White Pond, a large fresh water pond which is great for fishing, swimming or paddle boarding.... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy your vacation in this bright, open 3+ bedroom, 2 bath Chatham home on a cul-de-sac in a pleasant neighborhood. This home is only one-half mile to Cockle Cove Beach or 2/10th's of a mile to Taylor's Pond where you can launch a kayak to paddle into Nantucket Sound. New furnishings include a... View all property information
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    Chatham, Cape Cod 02659
    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
    1 / 19
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Lovely bright home with waterviews and central A/C in North Chatham ALSO AVAILABLE FOR HOLIDAY VACATIONS! Stunning, beautifully furnished home with central A/C and views of Pleasant Bay! Located in lovely North Chatham, this home is truly a special spot. The reverse floor plan maximizes views and... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    2017 Rental Rate: $3675 per week including the cleaning fee ~~ Off-Season: $2675 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Clean & comfortable 3-bedroom ranch with central air, located in the private neighborhood of Harding's Shores. New living room furnishings... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    16 SEA STRAND LANE (ID#109551) CHATHAM Charming and comfortable! Located in a quiet area within a short driving distance to both Hardings and Ridgevale Beaches. Air conditioning cools the home with units in every bedroom, including first floor master bedroom. WiFi, outdoor shower, washer/dryer,... View all property information
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    West Chatham, Chatham 02669
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    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    190 Countryside Drive - ID# 104736. Lovely 4 bedroom home in Chatham Charming 4 bedroom home in a peaceful area with a lovely fenced in yard. Just a short drive to Jackknife Cove beach on Pleasant Bay and a short distance to Monomoy River for kayaking and canoeing. School Houe Pond is a half mile... 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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    About this property
    Welcome to: Sandy Paws! 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'. A Complete renovation is taking place over the winter. Everything will be 'all new'! Peak Summer Weekly Rates:  last week of... View all property information
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    Chatham, Cape Cod 02633
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    Studio, 4 Bathrooms, Sleeps 8 | Quick View
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    $7,900/week Peak Season (July 1 - September 1) $5,800/wk for the weeks of (6/24 and 9/2) $5,200/week Shoulder Season (6/17 and 9/9) $5,000/week Shoulder Season (6/10 and 9/16) $4,000/wk (before June 10 and after September 23) This beautiful 4 bedroom, 3 bathroom custom-built Cape-style home is... View all property information
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    Chatham, Cape Cod 02633
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    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Smoking allowed
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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
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    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    Beautiful water views of Pleasant Bay from this charming, sprawling ranch which has 4 bedrooms and 3 baths. There is a spacious living room, dining room, large deck, all with spectacular views overlooking Pleasant Bay. Amenities include AC (central throughout + wall unit in master queen), washer,... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Come Stay at: Chatterbox! Location – Location-Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,000 - $4,200/week. Whether you Enjoy cocktails on the... View all property information
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    Chatham, Cape Cod 02633
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    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Lovely home with a/c near Ridgevale Beach RIDGEVALE BEACH 7/10 of a mile on Nantucket Sound!! Comfortably sleeps 10!! Cape Cod Bike Trail 8/10 of a mile away. Located at the end of a cul-de-sac and approximately 2 miles to the Village of Chatham for great dining, shopping, Cape Cod League Baseball... View all property information
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    South Chatham, Chatham 02659
    1 / 29
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • x
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    Schoolhouse Pond just 1/10 mile! Charming custom remodeled Cape Cod home, 1/10 mile to Schoolhouse Pond Beach--perfect for freshwater beach lovers. First floor offers open kitchen / living area with AC unit and one first floor queen bedroom with a ceiling fan. Second floor has three bedrooms all... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    $3,600/week Peak Season (July 1- September 2) $1,900/wk for the weeks of (6/24 and 9/2) $1,600/week Shoulder Season (6/17 and 9/9) $1,400/week Shoulder Season (6/10 and 9/16) $1,200/wk (before 6/10 and After 9/23) This light, bright two bedroom two bath Chatham rental cottage has panoramic views of... View all property information
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    Chatham, Cape Cod 02633
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    4 of 5 bubbles (1) Very good
    Studio, 2 Bathrooms, Sleeps 9 | Quick View
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    • x
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    This rental property boasts both a main house and fully equipped cottage, great for extended family or friends. The main house has 3 bedrooms and 1 full bath. Amenities include central AC on the first floor and window AC units in the upstairs twin bedroom, washer, dryer, dishwasher, TVs with... View all property information
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    Chatham, Cape Cod 02659
    1 / 15
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    OFF SEASON DISCOUNT is $125/night for 2 people, $15/night per additional person. Please see "Rates." (Does not include holidays.) The ''Chatham Retreat'' is clean, charming, and tastefully decorated. 1/5 mile walk to beautiful beach. You will enjoy this quiet neighborhood and lovely yard with... View all property information
    Location Information
    Chatham, Cape Cod 02659