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Holiday Rentals in Chatham, MA

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    €139
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    €631
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    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    €556
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    5 of 5 stars (4) Excellent
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    €1,948
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    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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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    €162
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    1 / 9
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    Freshly painted Cape Cod home tucked just off of Route 28 near the Chatham/Harwich line. Very convenient location with a quick walk to two great restaurants and .7 mile walk to Forest Beach, and Pleasant Street Beach. House includes an open living/dining area, a first floor master bedroom and... View all property information
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    5 of 5 stars Reviewed 7 January 2015
    Our family of four (children ages 12 and 14) stayed here August 2014. The property was well maintained, neat, and provided everything we needed, including sheets and beach...
    4 of 5 stars Reviewed 27 August 2014
    Adorable, comfortable home. Rooms and closets very spacious. Clean, well maintained. Children, 13, 13 & 10 loved it! Would def' return! Paula
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    €185
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    About this property
    Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village. View all property information
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    4 of 5 stars Reviewed 1 October 2014
    We enjoyed our stay at the condo in Chatham. It was comfortable for 3 people. It was clean and the kitchen was well stocked. Kris gave us excellent directions and suggestions.
    5 of 5 stars Reviewed 15 August 2014
    Having coffee each morning on the deck of this adorable cottage was one the highlights of my stay in Chatham. The view is terrific - of a lovely harbor that is called Mill Pond...
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    €1,298
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    1 / 11
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Adorable, cozy, renovated home - new to rental market. Air conditioned for comfort and WIFI for staying connected.Equipped with blu-Ray DVD, Dish TV with Blockbuster for streamed movies. Enjoy our gourmet kitchen with stainless steel appliances, a beautiful sunny living/dining area, deck and... View all property information
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    €487
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    1 / 15
    4.5 of 5 stars (4) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Overview Reviews (4)
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    About this property
    This lovingly restored Greek Victorian former bed and breakfast has 6 bedrooms and 5 full baths. Sleeps 12. Local lore has it that this property was floated over from Nantucket many years ago to its present site. Amenities include a Wolf range, granite counter tops, dishwasher, 2 cable TVs... View all property information
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    3 of 5 stars Reviewed 31 August 2013
    Pros:1-Location few miles from the center of town, 2-Walking distance from forest beach (not good for swimming). 3-Accomedate large groups. Cons:1-It is an old...
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    €185
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    About this property
    *** EARLY SEASON SPECIAL *** Rent for 7 days (Sat-Sat) and we'll waive the $125 cleaning fee. Valid 3/29/15 - 6/27/15 Welcome to our entirely renovated 'old Cape' cottage, with a sunny, open floor plan, brand new appliances and furnishings, washer/dryer and central air. After the beach, rinse... View all property information
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    5 of 5 stars Reviewed 29 March 2015
    My family absolutely loved staying in this cottage. My favorite time to visit the cape is in the fall - no crowds and the weather is usually still pretty warm. This cottage was...
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    €241
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    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (4)
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    • Smoking allowed
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    About this property
    This fully air conditioned 4 bedroom, 3 bath house on 1/2 acre lot sleeps 8 with 2 master suites! The main house has 3 bedrooms. One with a queen, one with 2 twins and one master suite with a queen. The 2nd master suite is located in a separate attached portion of the house with separate entrance.... View all property information
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    5 of 5 stars Reviewed 16 October 2014
    Stayed for a week in Oct and enjoyed every minute. Firstly, we booked the house at the very very last minute and the owners could not have been more obliging. They made their home...
    5 of 5 stars Reviewed 23 July 2014
    Perfect location to everything you could possible want to do. This rental makes you feel at home yet on vacation! Very spacious with everything you could possibly need. We loved...
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    €291
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    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    About this property
    Enjoy this spacious home on the Monomoy River with glimpses of Pleasant Bay. Recently renovated, our home boasts a gourmet kitchen with granite counters, 6 burner Wolf cooktop and Sub Zero refrigerator and wine frig . The kitchen opens to a deck perfect for al fresco dinners watching the sunset.... View all property information
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    5 of 5 stars Reviewed 2 August 2014
    I had never used "Flip Key" before and was a bit unsure of results. I have to say that this house was perfection! From my first contact with the owner to the day we walked out the...
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    €255
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    About this property
    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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    5 of 5 stars Reviewed 22 August 2014
    Exceptional accommodations complete with high end cookware , grill, 22 ft cu refer, and all other needed appointments . Well located for excursions to the Fish Pier; shops...
    5 of 5 stars Reviewed 21 August 2014
    Planning a visit to Cape Cod from the UK was always going to be tough when you weren't sure how best you might get around or where was best to stay. We couldn't have got it more...
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    €371
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    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    About this property
    This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Warm water, sunsets and miles of beach on Nantucket Sound awaits you just around the corner. This family friendly updated Cape Cod ranch has a large deck for outdoor entertaining surrounded by professionally... View all property information
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    €1,020
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    • Air Conditioning
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    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented... View all property information
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    5 of 5 stars Reviewed 17 October 2014
    The house was incredible. I have rented homes across the world with our family, and we are extremely picky in terms of 1. Cleanliness 2. renovation/newness 3. Location 4. Details...
    5 of 5 stars Reviewed 17 July 2014
    The units we rented at Oyster Pond exceeded our expectations. These two units (31 & 32) were very well appointed with TVs in every room, modern appliances, comfortable furniture...
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    €116
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
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    About this property
    ------------------------------------------------------------------------------------------------------ Like new 5 bedroom luxury Chatham vacation home on over 1 acre. Walk to Schoolhouse pond, clean freshwater pond with beach. Near the Cape Cod paved bike path and also only a few blocks to nice... View all property information
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    5 of 5 stars Reviewed 23 March 2013
    A group of friends stayed for a weekend reteat - and were so pleased with all the amenities of a fully equipped house and all the comforts of home, while staying on the cape...
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    €278
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    About this property
    Beautiful, Spacious, and Very Clean 3 bedroom 2 full bath home. Sleeps 8! Master suite with king size bed and private full bath. Large family room with entertainment system. Fully equipped kitchen with walk out deck. Private backyard with outdoor shower. One mile to ocean. Private pond... View all property information
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    2 of 5 stars Reviewed 3 July 2014
    * We have used Trip Advisor for several rentals and this one is best described as below average. Our extended family of 6 (4 adults, two kids) stayed in Beach Plum for 5 nights...
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    €116
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    1 / 12
    West Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, one bedroom with 2 twin beds... View all property information
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    €2,319
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    1 / 16
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
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    • Satellite TV
    • Washer
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    About this property
    2015 Rental Rates: $4750 per week, including the cleaning fee FRIDAY TO FRIDAY Rental. ~~ Off-Season: $2750 per week, including the cleaning fee Gorgeous beach house on a quiet street just steps to Ridgevale Beach! 'Beachy' decor and furnishings throughout! The first level has a great open floor... View all property information
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    €1,808
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
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    • Water Views
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    About this property
    Light and bright home with pretty marsh views from your back deck! Great, central location, close to Hardings Beach and a quick drive into downtown Chatham! You will love the screened porch or back deck for relaxing. AC units in every bedroom for the hot days, if you aren't at the beach! One... View all property information
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    €325
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    About this property
    This stunning 1 bedroom cottage is located right on the beach in Chatham, the best of Cape Cod. Perfect for a relaxing getaway, this cottage is steps from the sand, and is ready for your vacation! Amenities: Television, Cable, Wireless Internet, Full Kitchen with dishwasher, microwave, coffee... View all property information
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    €556
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    1 / 18
    South Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Dishwasher
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    • Fireplace
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
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    • Pets allowed
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    About this property
    Fabulous views of Nantucket sound are the focus of this newer home. Built in 2000, it sits at the end of a quiet dead end street overlooking an amazing view of nature, ocean and sky. From every window see Nantucket Sound, Hardings Beach and Stage Harbor Lighthouse. The house has an open floor... View all property information
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    €278
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    1 / 10
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or take extra bikes to ride to Lighthouse Beach/ Oyster Pond. Kitchen table has room for... View all property information
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    €397
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    1 / 22
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    About this property
    Classic North Chatham Escape, Pet Friendly $3,300 PRIME SUMMER WEEKLY RATE 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 updated kitchen with granite... View all property information
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    €238
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    About this property
    Enjoy in-town living. This bright two bedroom, two bath condo is a short walk to town, golfing, tennis, beaches and Chatham A's baseball games. This second level corner unit features a bright living room with eat-in dining room, kitchen and sliding doors to a walk-out balcony. All new furnishings... View all property information
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    €225
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    1 / 11
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
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    • Pets allowed
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    About this property
    Recently renovated cottage in sought after Cockle Cove beach neighborhood. Walk or bike 4/10ths mile to warm, sandy & family friendly town beach on Nantucket Sound. Direct waterfront location on tidal Taylors Pond, with stunning views and access to owner's private dock for kayaking & boating into... View all property information
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    €255
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
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    • Housekeeping...
    • Internet Access
    • Private Fishing...
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    • Pets allowed
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    About this property
    Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath home in Hardings Beach Hills is available to rent this season. With access to Buck's Creek flowing to Nantucket Sound, you can launch your kayak, fish or crab from the private association neighborhood dock and picnic area just... View all property information
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    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pets allowed
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    About this property
    Our Five bedroom Chatham vacation home is located on a quiet side street, yet near town. The five large bedrooms are added to by a den with double pull-out and a basement/play area with 2nd pull-out making it perfect for family groups, weddings, or reunions. We have 1 king bed, two queen beds, one... View all property information
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    1 / 12
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    CHARMING RENTAL THAT IS REASONABLY PRICED! Located on a great little side street....short drive to Nantucket Sound beaches, freshwater Schoolhouse Pond and grocery store. This three bedroom/two bath home offers a master bedroom with private bath, One portable air conditioning unit in the master... View all property information
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    €148
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    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Balcony
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    • Fireplace
    • Grill
    • Internet Access
    • Ping Pong Table
    Suitability
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    About this property
    The simple entrance path leads past rosa rugosa, wild roses, blooming yarrow, and other native flower beds to arrive to a spacious skylit great room, featuring vaulted ceilings and a wood-burning fireplace. The well-equipped kitchen, dining, and indoor living area has a bright indoor-outdoor... View all property information
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    €603
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    1 / 9
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    • Suitable for children
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    About this property
    Sit on the porch in one of the rockers and enjoy your morning coffee or afternoon beverage of choice and watch the world go by. As soon as you drive in the driveway and smell the salt air, you start to relax and feel the welcoming embrace of this historical in town main house and cottage. With five... View all property information
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    1 / 15
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    0.1 mile from popular summer Nantucket Sound beach can walk or ride or /access to private beach via path along marsh just steps away from the house quiet family area… ranch / cottage style house with summer beach flavor with views of Taylor Pond 1 bathroom / eat in kitchen / deck / Weber gas... View all property information
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    • Air Conditioning
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    • Water Views
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    • Suitable for children
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    About this property
    ON THE WATER ... * Beautiful water views! * Back decks open to mesmerizing views of Emery Pond * Hammock and patio furniture chosen for comfort and relaxation! * Direct access to pond from backyard. * Clean swimmable pond. * Bass fishing plentiful! * Gas grill. * 2.5 Blocks from Bike trail... View all property information
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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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    • Grill
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! So wanting for a nice clean quiet apartment unit close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the... View all property information
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    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Fireplace
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Walk to famous Lighthouse Beach (1/2 mile), walk to a beautiful private beach at the end of the road (200 yards) that is ideal for kayaking, clamming and enjoying the views, or take a walk from the private beach to South Beach and enjoy the solitude and seals. And for those who enjoy... View all property information
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    • Satellite TV
    • Waterfront
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This stunning 2 bedroom cottage is located right on the beach in Chatham, the best of Cape Cod. Perfect for a relaxing getaway, this cottage is steps from the sand, and is ready for your vacation! Amenities: Television, Cable, Wireless Internet, Full Kitchen with dishwasher, microwave, coffee... View all property information
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    North Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    • Satellite TV
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    • Pets allowed
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    About this property
    2015 Rental Rate: $4950 per week including linens and cleaning! ~~ Off-Season: $4250 per week including cleaning and linens Gorgeous new home in secluded North Chatham neighborhood. This home features hardwood floors, WIFI and central air. Lots of games, puzzles, sports and beach gear for the kids.... View all property information
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Satellite TV
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    • Pets allowed
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    About this property
    4 bedroom house with 2 master suites. Perfect for extended family and friends. Close to town and beaches. View all property information
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    €696
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    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Grill
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
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    About this property
    One of the most photographed Wind Mill homes on Cape Cod. Classic old world charm, coupled with all modern conveniences located near the beach and town. The Stony Hill Mill, constructed with 100 year old beams, river rock and barn board, is truly Cape Cod at its finest. This large stately home is... View all property information
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    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Air Conditioning
    • Balcony
    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Charming and romantic. It offers a bright second story loft bedroom, fitted with a queen bed with new orthopedic mattress. The ground floor features a large open living area with sunny full kitchen, dining space, comfortable sitting area with settee and club chair, and a simple cozy bathroom with... View all property information
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    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
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    About this property
    This stunning 3 bedroom cottage is located right on the beach in Chatham, the best of Cape Cod. Perfect for a relaxing getaway, this cottage is steps away from the sand, and is ready for your vacation! Amenities: Television, Cable, Wireless Internet, Full Kitchen with dishwasher, microwave,... View all property information
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    West Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    About this property
    SHORT WALK TO HARDINGS BEACH!! JUST A SIX MINUTE WALK (1/4 MILE) USING PRIVATE DEEDED PATH. Stroll to the beach in this lovely neighborhood without having to fight the crowds and traffic on busy roads. This immaculate four bedroom/three bath home has a true summer feel, very light and bright,... View all property information
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    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for... View all property information
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    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for... View all property information
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    €1,391
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    5 of 5 stars (2) Excellent
    Overview Reviews (2)
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    • Smoking allowed
    • Suitable for children
    • x
    • x
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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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    5 of 5 stars Reviewed 4 October 2014
    Loved the cottage, the view of Nantucket Sound and the serenity found only on the Cape. nine of the nicest days one could expect..
    5 of 5 stars Reviewed 17 September 2014
    This was my first stay on the Cape. Chatham is beautiful and the view from this home was incredible. Too bad the beach was not available as it is privately owned. Had to travel...
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    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Suitable for children
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    About this property
    JUST A SHORT DRIVE TO THE BEACH AND TOWN! This is a charming 4 bedroom (sleeps 10), 2 bath home offering CENTRAL AIR CONDTIONING AND WIRELESS INTERNET, washer/dryer, comfortable living space, dining area, fully equipped kitchen with dishwasher, large deck and fenced in back yard. Back yard is great... View all property information
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    5 of 5 stars Reviewed 26 August 2014
    The home is charming with recent updates and had a relaxed feeling to it. The yard was great for the kids to play in and to have barbeques. Even though the home is modest in...
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Dishwasher
    • Dryer
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    • Satellite TV
    • Washer
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    • Suitable for children
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    • Elder access
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    About this property
    OPEN WEEKS ARE (ALL OF JUNE, 6/27, 7/11, 7/18, 8/22, ALL OF SEPT.) CALL SOON TO BOOK RENT ME NOW ! OPEN WEEKS !        Private Home. All you need to pack are clothes. Everything is provided for that very special vacation adventure. Located in the highly sought after Sesuit Neck section of East... View all property information
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