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House Rentals and Beach Rentals in Chatham, MA

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    Travelers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 19
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 9
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 46
    5 of 5 bubbles (16) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    5 of 5 bubbles (2) Excellent
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Chatham Beach house... walk to Harding's Beach in Chatham. Wonderful home, great for families! Outdoor Shower, wrap-around porch with patio furniture and grill, hammock to relax, Cable TV, DVD player (family movies on site), wifi included, full kitchen, laundry, garage, plenty of parking. Just... View all property information
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed October 8, 2016
    I had no idea how large my family had grown until I set out to organize a weekend in Chatham, MA. We started as a family of 3; 2 little girls and a dad. Now we're a family of 10...
    5 of 5 bubbles Reviewed August 19, 2016
    What a perfect rental! From the beginning, owner Sue was extremely helpful and responsive. The beautiful pictures on the website don't even do it justice- the house was beautiful...
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    1 / 23
    5 of 5 bubbles (1) Excellent
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This bright and airy family-friendly home is just a 1/2 mile walk to this fabulous sandy beach where you can enjoy swimming both on Nantucket Sound or in the milder waters in the adjoining tidal creek. Ridgevale Beach is one of Chatham's most popular destinations for vacationing families. A clean,... View all property information
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    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed September 30, 2016
    We had a lovely weekend here while attending a family wedding. The house was comfortable and equipped with everything a family might need. The neighborhood is quiet and an easy...
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    1 / 20
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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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    Chatham, Cape Cod 02148
    5 of 5 bubbles Reviewed August 21, 2015
    This was a really beautiful home. An exciting mix of old and new, set on a lovely property, overlooking a lake. Sunrises and sunsets are breathless. Room enough for eight. State...
    5 of 5 bubbles Reviewed August 7, 2015
    Joy was a pleasure to work with. She was prompt with her communications to us. She explained everything we needed to do (having never done this before). The house was great...
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    1 / 41
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of quiet and accessibility for... View all property information
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    Chatham, Cape Cod 02650
    5 of 5 bubbles Reviewed September 23, 2014
    Amazing home with a great owner who was 100 percent accessible our whole trip. Huge house, our party of 10 didn't even know one another was there. Highly recommend the location...
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    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this traditional, yet well-appointed... View all property information
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    Chatham, Cape Cod 02633
    1 / 44
    5 of 5 bubbles (3) Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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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    South Chatham, Chatham 02659
    5 of 5 bubbles Reviewed October 31, 2016
    We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every...
    5 of 5 bubbles Reviewed September 15, 2016
    What a unique & wonderful house in Chatham!  John & Ruby are really superb hosts, very accommodating, making sure we were all set… to our delight, John even texted to let us know...
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    1 / 47
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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
    Location Information
    Chatham, Cape Cod 02659
    5 of 5 bubbles Reviewed October 31, 2016
    We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every...
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    1 / 17
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Location, location, location! Charming cottage-like apartment right across the street from the Cape Cod Coast and Lighthouse Beach. The unit is also within a ten minutes walk to the vibrant downtown area abound with eclectic shops and restaurants. This Hammond House unit has a beautiful water view... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed July 7, 2016
    My husband and I booked this vacation rental for the Fourth of July week and we really enjoyed our stay! Your right in the middle of the excitement a five minute walk to the beach...
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    1 / 7
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    About this property
    This property is not available after August 15, 2016. Charming Carriage House in fabulous location one street off Main St. near ball fields in quaint fishing village of Chatham, MA. Leave you car here as downtown is just a 10 minute walk, as is Oyster Pond. Also a short drive to the famous... View all property information
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    Chatham, Cape Cod 02633
    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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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    Chatham, Cape Cod 02669
    1 / 12
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Beautiful new condominium nestled on tranquil Perch Pond, located just a half mile from down town Chatham. This unit boast all the amenities of luxury living. Central A/C, gas fireplaces and granite tops to name a few. Spend your afternoons relaxing on the back deck overlooking the pond after a... View all property information
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    South Chatham, Chatham 02633
    1 / 11
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Please contact Courtney... View all property information
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    South Chatham, Chatham 02633
    1 / 16
    5 of 5 bubbles (1) Excellent
    West Chatham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
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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
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed July 29, 2016
    It was a nice little spot for my boyfriend and I to get away for the weekend. Had no issues with the facilities. Please keep in mind the cabin isn't air conditioned. There are...
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    1 / 34
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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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    North Chatham, Chatham 02650
    1 / 38
    West Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    About this property
    ACCOMMODATIONS: 3 bedrooms plus den with 2.5 baths. Accommodating 8-10 people. Master suite: king bed w/en suite Guest room 1: queen bed Guest room 2: four twin beds (2 bunks) Guest room 3: den w/full bed Living room Dining room seats 8 (addition kitchen table seats 2) Two full baths total... View all property information
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    West Chatham, Chatham 02633
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    RENOVATED very bright, beachy condo, 2bdrms/2bths. This unit comes equipped with AC, fully stocked kitchen and 2 decks to enjoy your wine/coffee. The decks overlook Little Mill Pound. This condo is located in town and the famed, kid friendly Oyster Beach & Lighthouse Beach are a 10 minute... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    North Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $2800 per week including the cleaning fee ***FRIDAY TO FRIDAY RENTAL*** ~~~ Off-Season: $2200 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean... View all property information
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    North Chatham, Chatham 02650
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    1 / 22
    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    0.1 mile from a 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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    South Chatham, Chatham 02659
    5 of 5 bubbles Reviewed July 11, 2016
    We absolutely loved our stay at this charming seaside home, it feels like someones primary residence not a rental. The home is bright, open and beautifully appointed, plenty of...
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    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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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    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
    1 / 8
    North Chatham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    2017 Rental Rate: $3225 per week, with the cleaning fee RENT 2 CONSECUTIVE IN SEASON WEEKS AND RECEIVE A $500 DISCOUNT! ~~Off-Season: $2225 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Spacious 5 bedroom on quiet cul-de-sac in prestigious North Chatham. Walk to beach,... View all property information
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    North Chatham, Chatham 02650
    1 / 17
    North Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    About this property
    2017 Rental Rate: $5350 per week INCLUDING linens & cleaning! Off-Season: $4900 per week INCLUDING linens and cleaning NO SHORT RENTALS Gorgeous home in secluded North Chatham neighborhood. The home features hardwood floors, Wi-Fi and central air conditioning with upscale furniture and appliances... View all property information
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    North Chatham, Chatham 02650
    1 / 20
    North Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 mile to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 2 miles to Main St., Chatham for shopping,... View all property information
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    North Chatham, Chatham 02650
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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 / 12
    South Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $1675 per week, including the cleaning fee Off-Season: $775 per week, including the cleaning fee Light and bright 4 bedroom home on quiet cul-de-sac in South Chatham. Comfortable furnishings throughout. Large upstairs bedrooms offer extra seating space too! Nice back deck off the... View all property information
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    South Chatham, Chatham
    1 / 23
    North Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    You will fall in love with this bright and cheery Cape! Wide planked Pine Hardwood floors in Living room and Dining room. Wide Galley Kitchen, fully equipped, including dishwasher, large side by side fridge and gas stove. New Furniture and Flat Screen TV in Living Room (not photographed yet). Wood... View all property information
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    North Chatham, Chatham 02650
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    255 Tanglewood Drive CHATHAM Just a short drive to many salt water beaches and fresh water ponds, as well as both downtown Chatham and Harwich Port, this house is convenient indeed! The backyard is fully enclosed and offers a great place to relax and grill after enjoying all the many things this... View all property information
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    Chatham, Cape Cod 02659
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2017 Rental Rates ~ In Season, $1125 including cleaning fee No Off-Season Clean rental home located just 1/2 mile to Hardings Beach or Oyster River Boatyard. Fresh paint and furnishings throughout make this small yet comfortable rental a great buy! Good size living room with high ceilings make it... View all property information
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    Chatham, Cape Cod 02633
    1 / 16
    West Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    64 Waveland Chatham Lovely home in excellent condition located just a short drive to Hardings Beach. This home has been well cared for and features two separate living areas with DVD players, large flat-screen TV s and expanded cable for Red Sox games. The town landing on Oyster River is just... View all property information
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    West Chatham, Chatham 02669
    1 / 27
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spend your Chatham vacation in this beautiful 4 bedroom, 2.5 bath home located 500 feet from Pleasant Street Beach. This is a truly unique, custom home featuring gorgeous woodwork throughout, a first floor master bedroom with Jacuzzi tub, a bright and beautiful kitchen with granite and silestone... View all property information
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    Chatham, Cape Cod 02659
    5 of 5 bubbles Reviewed August 19, 2016
    This is a WOW vacation home! Architecturally stunning with beautiful, upscale home furnishings. The home was bigger and more impressive than pictures were able to convey. Large...
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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. $1900 per week in season * $160 Cleaning Fee * $100 Handling Fee * $55 Damage Insurance OR $500 Security Deposit Please contact... View all property information
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    Chatham, Cape Cod 02633
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy this 3 bedroom, 2 bath Chatham home just minutes from the Cape Cod Rail Trail. The first level of the home features a kitchen with beautiful granite counter tops, separate dining area, living room and a Suite with a full sized bed and full bathroom. The second level has two additional... View all property information
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    Chatham, Cape Cod
    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
    1 / 12
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2017 Rental Rate: In Season, $3175 per week, including the cleaning fee No Off-Season Weekly rentals from mid-JUNE to mid-SEPT Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home offers... View all property information
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    South Chatham, Chatham 02659
    1 / 18
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $6250 per week, including the cleaning fee Off-Season $4450 per week, including the cleaning fee The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings and bed sets. The spacious open floor... View all property information
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    Chatham, Cape Cod 02633
    1 / 11
    South Chatham
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    2017 Rental Rate: $3000 per week including the cleaning fee ~~ Weekly rentals from mid-JUNE to mid-SEPT Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy, light and bright decor. Finished walkout... View all property information
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    South Chatham, Chatham 02633
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    South Chatham
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    2017 Rental Rate: $2275 per week, including the cleaning Off season, $1575 per week, including the cleaning Wonderful, clean, and comfortable home located in the quaint village of South Chatham. Enjoy your afternoons at the beach and your evenings in the bug free screened porch ! Within a quick... View all property information
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    South Chatham, Chatham 02659
    1 / 11
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    2017 Rental Rate: $5475 per week, including the cleaning fee Off-Season: $3725 per week (4 night minimum) including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated... View all property information
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    Chatham, Cape Cod 02633
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate ~ $1650 per week, including the cleaning fee Off-Season: $1200 per week, including the cleaning fee Comfortable summer rental home in a great central location! This three-bedroom ranch sits on a quiet street located in West Chatham. Just a quick drive in one direction to spend the... View all property information
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    Chatham, Cape Cod 02633
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2017 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL! ~~ Off-Season: $1400 per week including the cleaning fee !!! Weekly rentals from mid-JUNE to mid-SEPT Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate $3875 per week, including the cleaning fee Off Season, $2725 per week, including the cleaning fee Light and bright, this spacious beach home is located right down the street from family-friendly Hardings Beach. Plenty of room to spread out and relax as you enjoy your Chatham... View all property information
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    Chatham, Cape Cod 02633
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rate: $2175 including the cleaning fee Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely home, on 1/2 acre wooded lot, only 1/2 mile to the warm waters of kid-friendly Ridgevale Beach! This comfy, spacious home features high speed... View all property information
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    Chatham, Cape Cod 02633
    1 / 15
    5 of 5 bubbles (1) Excellent
    South Chatham
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
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    About this property
    OWNER'S SPECIAL - Book before July 4th and get $200 off weekly rate! Beautiful Chatham Get-away! Located on a sandy, dead end lane, this cottage is the perfect summer get-away. A large screened in porch fronts the cottage and is the perfect place for meals or evening game nights! Beautiful... View all property information
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    South Chatham, Chatham 02659
    5 of 5 bubbles Reviewed September 4, 2016
    As a first time traveller to Cape Cod this cottage was everything I imagined ! Beautifully decorated and everything you required . My family loved it and we had great fun playing...
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2017 Rental Rates: ~~~Pre-season (May 13-June 16) $1,200 per week ~~~IN SEASON: $1800 per week (June 17-Sept 9) ~~~Post-season (Sept 9-Oct 14th) $1,200 per week Off-season (subject to Owner's prior approval) $800 week $175 MANDATORY cleaning fee per lease Weekly rentals from mid-JUNE to mid-SEPT... View all property information
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    Chatham, Cape Cod 02633
    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 / 16
    South Chatham
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    • x
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    2017 Rental Rates: $2600 including the cleaning fee. Off-Season: $1700 including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Wonderful, light and bright summer home located just steps from Taylor's Pond, the Eel River and the warm waters of the Nantucket Sound. Even better, there is a... View all property information
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    South Chatham, Chatham 02659
    1 / 21
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    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
    Location Information
    South Chatham, Chatham 02659
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