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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.
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    €6,701
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    5 Bedrooms / 5 Bathrooms / Sleeps 16
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    €938
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    €2,234
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    4 Bedrooms / 3 Bathrooms / Sleeps 12
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    €201
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Located in Chatham, this 4 bedroom 2 bath Cape Cod vacation rental home has window A/C units in the upstairs bedrooms as well as the 1st floor bedroom and living area to keep you cool and offers WiFi to keep you connected. .3 miles to Ridgevale Beach. Through the side door off of the driveway,... View all property information
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    1 / 27
    4 Bedrooms / 2 Bathrooms / Sleeps 9
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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 wall AC unit and one first floor queen bedroom with a ceiling fan. Second floor has three bedrooms... View all property information
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    €3,127
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    1 / 12
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Lovely renovated home with central air just steps away from Lighthouse Beach. Lovely renovated home just 5 doors down from beautiful Lighthouse Beach- you don t have to worry about parking! This home features many upgrades including central air conditioning and lovely, comfortable living spaces. So... View all property information
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    €3,216
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    1 / 21
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    $3,600/week Peak Season (June 27 - September 5) $3,000/wk for the weeks of (6/13 and 6/20 and 9/5) $2,000/wk 9/12 $1,500/wk (before June 12 and after 9/19) Spectacular custom built 4 bedroom 2.5 bathroom home located just 1/2 a mile to Pleasant/Forest Beaches. This spacious Chatham rental home had... View all property information
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    €983
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    1 / 10
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    2015 Rental Rate: $1725, including the cleaning fee Off Season: $1225, including the cleaning fee Traditional Cape Cod ranch with three bedrooms and central air conditioning. Great neighborhood for kids and about one mile bike ride down to Hardings Beach. Good walking and bike riding area. Air... View all property information
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    €2,680
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    1 / 31
    South Chatham
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Waterfront
    • Water Views
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    About this property
    ID # MEET580 Superb Chatham location in Retreat style setting, this expansive home accommodates up to 10 guests in delightful comfort. [~]This exceptional home set on 2.4 acres with pond views and pond access, lush yard with adventurist zip-line, seating surrounded fire pit, basketball court, and... View all property information
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    €634
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    1 / 8
    1 Bedroom / 1 Bathroom / Sleeps 2
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    About this property
    393 STONY HILL ROAD CHATHAM Charming and completely renovated cottage, 7/10 of a mile to Scatteree Beach and the Cow Yard Landing and under 2 miles to Main St., Chatham for shopping, dining, and ice cream! This adorable one bedroom, air conditioned cottage has vaulted ceilings, exposed beams, a... View all property information
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    €1,072
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    1 / 10
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    2015 Rental Rate: $1775 per week including the cleaning fee ~~ Off season: $1375 per week including the cleaning fee Here is a great deal!! Clean and spacious 3 bedroom, home that sleeps 8 people comfortably, with plenty of room to spread out. This centrally located home is convenient to the bike... View all property information
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    €983
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    2015 Rental Rate: $1775 per week with the cleaning fee ~~ Off Season Rate: $1250 per week with the cleaning fee. Fabulous remodeled home in a great central location, close to downtown and Oyster Pond Beach. Filled with comfy furnishings, this 3 bedroom ranch is light and bright, with a large deck... View all property information
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    €153
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    1 / 6
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Waterfront
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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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    €1,965
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    1 / 16
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    2015 Rental Rate: $3000 per week including the cleaning fee. ~~ Off-Season: $2400 per week including the cleaning fee This recently renovated four bedroom beach cottage is in the heart of the beautiful and kid-friendly Hardings Hills area. It offers a bright and sunny kitchen with shiny granite... View all property information
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    €230
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    1 / 22
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Private, Family Ranch Style Riverbay home in Chatham for your Cape Cod Vacation located on a dead end road. As you enter the through the front door you will find comfortable seating in the living room with a flat screen TV. There is a hallway leading you to the bedrooms on the left. Straight ahead... View all property information
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    Spend your Cape Cod vacation in this 3 bedroom 2 bathroom rental home close to the downtown area. Amenities include washer/dryer, dishwasher,Wi-Fi, air conditioning (central on 1st floor and a window unit in each of the upstairs bedrooms as well as ceiling fans), expanded cable TV (with NESN, ESPN,... View all property information
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    €1,876
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    The location of this cottage is ideal ~ it's nestled off the main road between downtown Chatham and Andrew Hardings Beach. This is a quaint 2 bedroom 1 bath house. You can enjoy shopping, fine restaurants, band concerts, ball games and much, much more. Amenities include washer/dryer, dishwasher,... View all property information
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    €536
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    1 / 11
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    2015 Rental Rate: Pre-season (May 23-June20) $1,200 per week ~~~IN SEASON: $1800 per week (June 20-Sept 12) ~~~Post-season (Sept 12-Oct 17th) $1,200 per week Off-season (subject to Owner's prior approval) $600 week $175 MANDATORY cleaning fee per lease Light and airy - hardwood floors, lots of... View all property information
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    €1,117
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    1 / 16
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Pets allowed
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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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    €1,429
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This wonderful 3 bedroom 2 bath house is in a quiet neighborhood yet close to shopping, restaurants and beaches. There is access to a nearby path leading right to Ridgevale Beach (about 8/10ths of a mile long) and also is only a short drive to Hardings Beach. This house has a washer/dryer,... View all property information
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    €1,697
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    1 / 12
    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    About this property
    60 Hallet Lane - ID# 104906. In the heart of the Old Village Antique home in the heart of Old Chatham Village. Convenient to Lighthouse Beach, Village shops and restaurants. Five Bedroom, 3 Bath, 4/10 mile to Lighthouse Beach. $2500 per week in season with a $210 Cleaning Fee. Please view our... View all property information
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    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    Enjoy the views of Nantucket Sound from every floor of this recently updated, lovingly and meticulously maintained, 3 bedroom 2 bathroom Chatham rental property. It's a perfect balance between having all of the modern amenities, with an open, light and bright feel while still maintaining the true... View all property information
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    1 / 10
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    PERFECT GETAWAY THAT IS SO CLOSE TO THE BEACH AND PET FRIENDLY!!! This cozy, comfortable beach cottage is located in the Horne Cottage area and is a five minute walk to beautiful beach just south of Lighthouse Beach near Outermost Marina. Lighthouse Beach is also about a 10 minute walk from this... View all property information
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    €1,608
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    1 / 10
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    2015 Rental Rate: $1950 per week, including the cleaning fee ~~ No Off-Season Great beach cottage, recently updated with new paint, new beds, and renovated bathrooms! Lovely new hardwood laminate flooring throughout! Located within walking distance to the kid-friendly warm waters of popular... View all property information
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    €3,127
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    4 Bedrooms / 5 Bathrooms / Sleeps 10
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    About this property
    2015 Rental Rate: $5000 per week, including the cleaning fee Off-Season $3750 per week, with the cleaning fee Beautiful North Chatham home with peeks of Crows Pond and three decks! This year-round home is filled with upscale furnishings and decor. It offers two large separate living spaces, a... View all property information
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    €1,340
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    2015 Rental Rate: $2350 per week, including the cleaning fee ~~Off-Season: $1650/week, including the cleaning fee. Light and bright cottage just steps to the warm Nantucket Sound waters of Pleasant Street Beach! Tasteful, traditional furnishings throughout. New appliances and stone counters in... View all property information
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    €737
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    2015 Rental Rate: $1225 per week including the cleaning fee ~~ Off-Season: $950 per week including the cleaning fee Adorable one bedroom unit just steps to Lighthouse Beach! A quick walk to downtown Chatham for dinner, shopping and more, this charming condo is perfect for a two people, but there is... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    2015 Rental Rate: $1725 per week including the cleaning fee ~~ Off-Season: $1225 per week including the cleaning fee Charming three bedroom cottage located at end of dead end street near Cockle Cove Beach. Quiet setting and you can enjoy the cozy deck overlooking the salt marsh. Ride bikes down to... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    2015 Rental Rate: $2075 per week, including the cleaning fee~~~~~Off-Season (June only): $1475/wk including the cleaning fee Spacious home on quiet street in the village of South Chatham. Plenty of room for two families, with 4 bedrooms and two living areas. Relax in the light and bright sunroom,... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    2015 Rental Rate ~~ $1500 per week, with the cleaning fee ~ Off-Season is the same rate ~ OFF Season is negotiable Enjoy everything Chatham has to offer from this perfect, small home centrally located to beaches and downtown. Light and bright furnishings. A fantastic deck in the back of the home... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Wonderful home to spend the summer in. Lighhouse beach and Oyster Bay are near by. This home sleeps 6 people. Relax at the end of the day on your own deck. Additional amenities include: queen beds(1), double beds(1), general amenities, single beds(2). View all property information
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    €849
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    2015 Rental Rate: $1325 per week, including the cleaning fee ~~~ Off-Season: $1075 per week, including the cleaning fee Charming cottage in the woods and only 2 minutes to Oyster River Public Boat Landing. Small screened-in porch attached. A great vacation cottage for a small family. Each bedroom... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    WALK TO TOWN LOCATION!! Spectacular rental property located just a short walk to restaurants, shops, Chatham Bars Inn, Seaside Links 9 Hole Golf Course, Chatham Angler's Ballfield, town playground and Oyster Pond beach area. This immaculate rental has so much to offer....four bedrooms/2.5 baths,... View all property information
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    €625
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    4 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Pets allowed
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    About this property
    180+ photo gallery available upon e-request. This exquisitely furnished four bedroom home is located on the Ocean side of Shore Road with an easy walk to Chatham's beaches, Fish Pier, Lighthouse, town center, outdoor band concerts and fine restaurants. Just minutes walk from The Chatham... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    Situated in a wonderful neighborhood at the end of a cul-de-sac with a great yard for the kids, this four bedroom two bath cottage is only 5/10ths of a mile from Nantucket Sound Beaches. Its features include central air, washer/dryer, dishwasher, cable TV (includes NESN, ESPN, Weather Channel,... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    2015 Rental Rate: $1800 per week, including the cleaning fee ----Off Season: $975 per week, including the cleaning fee Cute 3 bedroom ranch, walking distance to town and Oyster Pond. A great new 2nd family room just finished in the lower level! No deck, but there is a picnic table in the backyard.... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    The charming, sprawling ranch has 4 bedrooms and 3 baths. There is a spacious living room, dining room, large deck, all with spectacular views overlooking Pleasant Bay. This property has access to its own private beach as well as a float tie-up for a boat up to 24'. Amenities include A/C (central... View all property information
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    €715
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Waterfront
    • Water Views
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    About this property
    2015 Rental Rate: $1525 per week including the cleaning fee ~~ Off-Season: $925 per week including the cleaning fee Light and bright two bedroom condo near Lighthouse Beach. New carpeting, new furniture, and new hardwood floors really brighten up the decor. Many updates in 2013, including new... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    Enjoy your summer vacation in this charming 3+ bedroom 2 bath home that is located 7/10ths of a mile to Nantucket Sound beaches. Situated just 2/10ths of a mile to Mill Creek which is great for kayaking and canoeing into Nantucket Sound or Taylor's Pond. Amenities include washer/dryer, dishwasher,... View all property information
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    North Chatham
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    2015 Rental Rate ~ $6300 per week, including the cleaning fee and the linens and bath towels Off Season ~ $4300 per week including the cleaning fee and the linens and bath towels Gorgeous home conveniently located to everything Chatham has to offer! Beautiful upscale kitchen featuring all new,... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    SHORT DRIVE TO THE BEACH AND AROUND THE CORNER TO THE BIKE PATH!! This immaculate 4 bedroom, 2 bath home was completely renovated in 2010, with central air conditioning, master bedroom suite with private bath, wireless internet, washer/dryer, fully equipped kitchen with dishwasher, sunny dining... View all property information
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    1 / 19
    South Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This ranch style Cape Cod Vacation Rental home in Chatham has undergone a complete refresh with all new --paint, new bathroom, kitchen, flooring, furniture and landscaping. A/C units in the bedrooms on the main floor and wifi too.​ This home is South of Route 28 and you have your choice of Pleasant... View all property information
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    South Chatham
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Spend your summer vacation in this 3 bedroom 1 bath South Chatham vacation cottage. It is only 2/10ths of a mile to Forest Beach and located in a quaint, beach neighborhood. It has many convenient amenities such as cable TV (includes sports, etc.) with DVD player, WiFi, washer/dryer, enclosed... View all property information
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    €3,395
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    $3,800/week Peak Season (July 18 - August 28) $3,300/week Shoulder Season (June 27 - July 17) $3,300/week Shoulder Season (August 29 - September 4) $2,400/week Off Season (anything prior to June 27 and anything after September 5) This beautiful newer home is located in Hardings Beach Hills 5/10ths... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    About this property
    52 PLEASANT STREET NEW for 2015 SEASON CENTRAL a/c. Easy access to Pleasant Street Beach. The property has 3 bedrooms, two with 2 single beds and one with a queen size bed all on one level. Amenities include an enclosed porch, outside shower and WIFI. This property rents for $1,750 per week in... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Satellite TV
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    • Waterfront
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    • Pets allowed
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    • Suitable for children
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    About this property
    2015 Rental Rate ~~ FRIDAY TO FRIDAY: $12,550 per week, including the linens and cleaning fee Off season $8550 per week including the cleaning and linens This one of a kind secluded residence overlooking a stunning Chatham Seascape exudes timeless elegance and charm. Set within a spectacular... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Satellite TV
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    About this property
    ID #PATT41 Chatham Vacation home, only 0.1 miles to Ridgevale Beach which is next to Cockle Cove Beach on Nantucket Sound, with beach access from Bucks Creek Bridge from Nantucket Drive. [~]Catch views of Buck Creek and the Ocean beyond from the living room of this vacation cottage that has a... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    About this property
    In town location, walk to Claflin s Landing. Located on Seaview St. Walk to Seaside Links Golf Course. 4 bedrooms and 2 full bathrooms. Additional amenities include: queen beds(1), double beds(1), general amenities, sofa beds (queen)(1), single beds(3). View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Enjoy your vacation and be close to Nantucket Sound at this adorable 2 bedroom cottage only 3/10ths of a mile from Nantucket Sound beaches. This property has one portable A/C unit in the bedroom with Queen, washer/dryer, digital cable TV (includes NESN, ESPN, etc..) with DVD, WiFi, gas grill,... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    2015 Rental Rate: $2175 per week, including the cleaning fee ~~Off-season: $1475/wk, including cleaning fee Lovely updated cottage located in the popular Harding's Hills neighborhood. Spacious master bedroom with cathedral ceiling and private bath. The kitchen is also updated, light and open. There... View all property information
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