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Chatham Cottages

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    Travellers to Chatham are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    25 Matching Rentals in ChathamView all 456 rentals
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    All New Cottage in Chatham Near Hardings Beach1 / 19
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Quiet Lakeside Cottage - Ideal for Couple1 / 14
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Captain's Haven1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Ides of Marsh1 / 12
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Internet Access
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    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    $1150/week-High Season-lower other times Foote-steps Chatham Charmer - Weekly Rentals The charm of a Cape Cod cottage with all the amenities of home. Relaxation and conveniences on a private circle with idyllic nature views... Enjoy our enclosed porch overlooking the salt marsh and a short (4/10...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    cape cod charming family friendly chatham cottage .01 mile to Cockle Cove Beach1 / 22
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Outdoor Dining Area
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3.5 bedroom and 2 full bath dog-friendly vacation home in Chatham with beautiful marsh views is just a half mile from Hardings Beach and Oyster Pond River. This home offers such amenities as a washer/dryer, 3 A/C units, dishwasher, cable TV, WIFI, and a gas BBQ grill. The first bedroom,...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Patio
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This impeccable 2 bedroom and 1 bath cottage in Chatham is close to beaches, town, great restaurants, and unique shops. But you will be insulated from the summer crowds the moment you arrive at Waterview Colony, a serene retreat set on 5.5 acres with a private beach on White Pond. Recently...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cape Cod Pine Grove Cottage - 1/2 mile from beach!1 / 15
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 1, 2014
    We loved being so close to Cockle Cove Beach. The outside shower was a hit, too. My two teenaged boys loved, loved, loved this place. It would be even better if it had wifi.
    Reviewed August 25, 2014
    I was so happy with our stay! the cottage was very cute and was just enough room! it was close to just about anything you can want to do in the cape. the welcome gift was very...
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    About this property
    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes....
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
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    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    19 Glendon Way, S. Chatham Casual knotty pine summer cottage just 1/2 mile to Pleasant Street Beach. This 3BR/1BA single level cottage is located in a nice quiet neighborhood of South Chatham. Convenient to shopping - just a 10 minute drive into town. $1000 per week * $100 Handling Fee * Choice of...
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    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Friday to Friday Rental This cottage is converted out of an a barn built in 1792. The upstairs bedroom has a full bed and the downstairs bedroom has a day bed (2 twin beds). This cottage is not for everyone. The entrance to the upstairs bedroom is steep and 18' wide. You can see it next to the...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Parking
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this lovely Chatham vacation rental located in desirable North Chatham near, gorgeous beaches, restaurants & Chatham Village. Here you can enjoy everything Chatham has to offer, from Chatham baseball games, the village area with restaurants & shops, Lighthouse beach & more! Gorgeous...
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    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Grill
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    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2017
    Our stay at Pleasant Forest Shores was awesome! The cottage was very clean, had a sizable living room & kitchen and was located within a quiet neighborhood. It was also about...
    Reviewed July 1, 2017
    We actually stayed in cottage #2 but they appear to fairly similar. I used to vacation in Chatham as a kid in the late 60's and early 70's. These cottages are VERY reminiscent...
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    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...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Porch
    • Wi-Fi
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 22, 2017
    I admit I ended up here somewhat by accident, but it was a fortuitous accident. Not only is this small cottage colony (5 cottages) perfectly located to get to a variety of...
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    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...
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    Location Information
    South Chatham, Chatham 02659 1525
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute cottage only 1 mile to Hardings Beach! 2 bedroom, 2 bath Cape Cod Cottage! Well maintained and appox. 1 mile to Hardings Beach in Chatham. Relax and dine in the screened porch which expands across the front of the cottage. This neighborhood is located off Barn Hill and a short distance to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    ENCHANTING COTTAGE FOR 4 CLOSE TO FOREST BEACH IN CHATHAM! PET FRIENDLY!1 / 16
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2017
    Pet friendly, clean, and the beach is a walk away! All amenities available at the house: grill, beach toys, games, etc. We loved our stay!
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    AFFORDABLE DREAM BEACH HOUSE IN CHATHAM WITH LARGE FRONT AND BACK DECKS, ROOM FOR 6, AND ONLY STEPS TO FOREST BEACH! PET FRIENDLY! There is a dreamlike quality to this 3 bedroom/1 bath cottage just down the road from Forest Beach in Chatham. Maybe it's the storybook shutters flanking every bedroom...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    96 Water Street CHATHAM Charming light and bright 2 bedroom cottage in the Old Village, close to both town and Lighthouse Beach. The cottage shares a yard with the Main house. $1850 per week * $100 Handling Fee * Choice of $500 Security Deposit or $55 Vacation Renter Damage Fee * $100 Cleaning...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    16 ELLIS Pet friendly home in Chatham sleeps 4. Two bedrooms one with a queen and bedroom two has a queen and a single bed. Outdoor seating on the deck is spacious. Enclosed outside shower. One and a half baths. WiFi. A/C in the bedrooms. A short drive to Harding beach. FRIDAY arrival and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    NOTICE: This listing is missing some pix still as created it quickly due to a recent cancellation so look for more pix elsewhere. Yes, the price is very low but that's why SO many customers have come for years/decades/generations and why I have so few openings, ESPECIALLY during the mid-July to...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chatham Cottage1 / 11
    (2)Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    • Private Garden
    • Outdoor Dining Area
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 7, 2015
    This traditional yet very spacious Cape Cod cottage is perfectly situated in a quiet neighborhood on an lightly traveled road. It is a most pleasant five minute walk from the...
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    About this property
    This Chatham cottage has a cozy, comfortable living /dining area and three bedrooms. There is a large, sunny deck with table and chairs for outdoor dining and a picnic table on the shady side of the house. The two dedicated parking spaces make for easy parking. It is a short walk to beautiful...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the ultimate Chatham getaway at this 2-bedroom, 1-bathroom 'Carriage House' cottage that comfortably sleeps four. As part of a compound that overlooks the beautiful Oyster Pond, you can enjoy lovely views from multiple rooms in the cottage, as well as from the pristine, lush yard. This home...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get a dose of classic Cape Cod charm from 'The Windmill,' a 1-bedroom, 1-bathroom vacation rental cottage that sleeps 3 in Chatham! This nautical nook is the perfect size and layout for a couple's retreat or small family getaway, offering all you need to make you feel right at home. Enjoy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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