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Holiday Homes in Chatham

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    Travellers to Chatham are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 389 Rentals in Chatham
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    Cape Escape Chatham Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 53
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Walk to Ridgevale Beach From Family Friendly Home1 / 23
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    All New Cottage in Chatham Near Hardings Beach1 / 19
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Grill
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2018
    Recently rented this cottage for a week and it was wonderful. Everything was set up so nice and the renting process was made seamless by the owners. It felt like we were the...
    Reviewed 7 November 2015
    Wonderful house, very nice quiet location within easy reach of beaches. House very clean with everything that we needed. Would highly recommend.
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    About this property
    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 off in the private outdoor shower before relaxing on the sunny patio. The Space: Create cherished family memories in our...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    02633, Chatham, Cape Cod
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Beach Chic Cape Escape! Chatham 5 Star Private-Newly Renovated 5m walk to beach1 / 54
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 September 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...
    Reviewed 2 May 2016
    Plusses:* Kitchen is fully equiped and the stove is big and of excellent quality.* Showers have a lot of power.* Good size house (big living room, separate dining room, big...
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    About this property
    Newly renovated kitchen with quartz “Sea Glass” countertops, backsplash and Nantucket farm sink. Truly a well equipped cooks kitchen. This year round low allergen, open concept home has 3 bedrooms, 2 newly updated baths, a large two level outdoor deck with electric retractable awning, creating a...
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    02659, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 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 1 July 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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    02659 1525, South Chatham, Chatham
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to ChathamBeachCruiser! Relax in our 5 bedroom home with central air. The entire house is equipped with all new furniture in June of 2016 and a few antiques (including a coffee table made from a real ship’s wheel). The house sits at the end of a private drive with plenty of parking. This...
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    02650, North Chatham, Chatham
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Beautiful sunsets in Chatham!1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Outdoor Dining Area
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    We had a wonderful time in Chatham. Joy's house was beautiful. Spacious and really well designed with lovely views over a lake; and located on a quiet private road. The outside...
    Reviewed 29 July 2018
    My son proposed to his girlfriend on Jackknife Beach (a short walk away) while we were on vacation here. It’s a beautiful home. Would highly recommend it if your looking for a...
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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 . Extra bonus: a second dishwasher and frig in the laundry room offof the kitchen!...
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    02148, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 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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    02659, South Chatham, Chatham
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2017
    Would totally stay here again. Super clean & comfy, plenty of room for 3 adults & a dog, nice quiet neighborhood with friendly neighbors, close to beach. Had one small...
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    02659, South Chatham, Chatham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, 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
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 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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    02659 1525, South Chatham, Chatham
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath (+ outdoor shower) 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...
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    02669, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    • Parking
    • Porch
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    • Cable/satellite TV
    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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    02659, Chatham, Cape Cod
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Captain's Haven1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 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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    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...
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    02633, West Chatham, Chatham
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • Private Garden
    • Air Conditioning
    • Grill
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    Suitability
    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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    02659, South Chatham, Chatham
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Quintessential Cape Cod Vacation Home in N.Chatham1 / 41
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    • Balcony
    • Grill
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 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...
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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...
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    02650, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our highly rated & reviewed 3 bedroom 1 & 1/2 bath home is nestled on a quiet side street just 3/10 tenths of a mile from one of the best beaches in Chatham...Forest Beach. Our comfortable home is 1100 square feet; and is updated & modern with Air Conditioning, Wi-Fi & a 50'' LCD TV... yet it...
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    02659, South Chatham, Chatham
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Former Chatham Bed and Breakfast1 / 12
    (4)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Outdoor Dining Area
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    02659, Chatham, Cape Cod
    Private Room - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Quiet Lakeside Cottage - Ideal for Couple1 / 14
    (18)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We had a wonderful stay at Helene's cottage. Great location for bike riding, swimming and canoeing. Our host provided many local areas of interest in the form of a binder...
    Reviewed 8 August 2018
    This cottage is a one bedroom on White Lake, nestled amount trees and other cottages. It is charming and a very comfortable way to spend a week in the Chatham, MA area. The...
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    About this property
    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming, kayaking and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to Summer Oasis! Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9.   A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0.6 mile)! Central air, free WiFi, a screened in porch, 3 spacious bedrooms, and open concept...
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    02659, South Chatham, Chatham
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Light & Bright Chatham Home, Walking Distance to Beach Linens Included, Pets Considered Peak Weeks - $2,000 Rents Saturday - Saturday during peak season Please note:  This property is part of a larger estate, and is only available to rent individually in the months outside of July and August...
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    02650, North Chatham, Chatham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    7 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    About this property
    Historic North Chatham Estate. Sleeps 20, private beach! Linens included and new beds/furniture for 2018 Peak Summer Weekly Rates: $9,900 - $15,900 Rents Saturday to Saturday during peak season Two-night rentals available in the offseason   Please click on the 'Virtual Tour' to see a 3D tour of the...
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    02650, North Chatham, Chatham
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 24
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy fantastic, unobstructed views of Red River Beach and Nantucket Sound from this 3 bedroom, 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. The property comfortably accommodates 8 people however can take up to 10 with the use of the full-size sleep...
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    02659, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chatham 1 Bedroom Beachfront Old Village1 / 9
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Waterfront
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    • Patio
    • Cable/satellite TV
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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.
    Reviewed 14 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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    About this property
    Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village.
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on its own point within exclusive and private Stage Island, this Chatham home offers both an idyllic setting and modern comforts. Enjoy stunning views over Stage Harbor throughout the home and direct water access from the private dock (boats under 20' can be brought and tied up for your...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
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    4 Bedrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    key # 158 Additional amenities: 1/2 Bath 2, A/C Units 4 ~ 1 in each BR, Area Town, Bedding rm1 King Ensuite ~ 2nd Fl., Bedding rm2 Queen ~ 1st Fl., Bedding rm3 Two Twins ~ 2nd Fl., Bedding rm4 Two Twins ~ 2nd Fl., Bedrooms 4.00, CD, Dist. To Downtown 3/4 mile, Distance to Beach 7/10 mile, Fans 4,...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Private Garden
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house has been beautifully updated...
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    Location Information
    02659, South Chatham, Chatham
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Washer
    • Grill
    • Balcony
    • Terrace
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 minutes to Harding Beach, 10 minutes to downtown Chatham This bright and cozy 4 bedroom, 1.5 bathroom home is located in a quiet neighborhood just minutes from downtown Chatham. Walk to a scenic town landing on Oyster Pond River, or drive to popular Harding Beach in less than 5 minutes. Oyster...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Location Information
    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious Custom Chatham Home Plus Guest House Linens included, new furnishings, hot tub, bocce court Peak Summer Weekly Rates: $12,500-$13,900/week Rents Saturday to Saturday in peak season NEW for 2019 -- Heated pool and spa! This immaculate custom home is set close to everything in Chatham....
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    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    Brand new custom built beauty in South Chatham with water views (linens included) Peak Summer Weekly Rates: $7,400 - $8,900 Rents Saturday to Saturday during peak season Be among the first to vacation at this wonderful custom-built home in South Chatham. Just finished in January 2017, this...
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    02659, South Chatham, Chatham
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 9
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Chatham Family Compound Sleeps 16   Walk to Public Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900  Rents Saturday - Saturday during peak season   Please click on the 'Virtual Tour' to see a 3D tour of the home Welcome to sublime summer living at the Chatham shore. Located...
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    02650, North Chatham, Chatham
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This 4 bedroom, 2.5 bathroom house is within walking distance to downtown Chatham with some of the best restaurants and shopping that Cape Cod has to offer. The living room offers plenty of new, comfortable seating and the kitchen, with granite countertops and stainless appliances, is fully...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chatham Cape Cod Waterfront Vacation Rental (8927)1 / 18
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Reviewed 3 September 2016
    Chatham Vacation rentals followed our guidelines and helped us find the perfect vacation house. Home had exquisite views of Pleasant Bay - private pier was a bonus House was...
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    About this property
    Magnificent waterfront home with views of Pleasant Bay, North Beach and the Atlantic beyond. This updated and well-appointed 4 bedroom, 3 1/2 bath home is located in an association neighborhood, water-front home with breathtaking views of Pleasant Bay, North Beach and the Atlantic beyond. The...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Smoking allowed
    About this property
    Brand new custom built beauty in Chatham, walk to Ridgevale Beach! (linens included) Peak Summer Weekly Rates: $6,300 - $7,200 Rents Saturday to Saturday during peak season NEW Listing for 2018!  This brand new custom home provides a luxurious vacation experience just a short walk from...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Terrace
    • Patio
    • Central Heating
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    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to downtown Chatham, great views, some of Stage Harbor, walks on the beach at Stage Harbor, lighthouse beach, fish pier, restaurants, shops. Good for couples and families. Sited on Chatham's historic Loop ...The Ensign Nickerson House is steps to Stage Harbor and Port Fortune Lane with marsh...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    02650, North Chatham, Chatham
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Parking
    • Outdoor Dining Area
    • Grill
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    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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    02659 1525, South Chatham, Chatham
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Private Contemporary Cape Set on a Hilltop1 / 20
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Internet Access
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    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2018
    Had a great stay with my family. It was quiet, relaxing, very well stocked with everything we needed and conveniently located. Would highly recommend.
    Reviewed 19 August 2016
    We are a family of four travelling from the UK and stayed at the property for one week in July. Chatham was a relaxing week after our whirlwind tour of Florida and New York. We...
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    About this property
    You will enjoy easy times in this 3 bedroom 2 bath Cape set on a hilltop. This very well-equipped house is at the end of a cul-de-sac and offers complete privacy, a large deck with grill, outdoor shower, and ample parking. It has a contemporary open and airy floor plan with cathedral ceilings and...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham!  Offering Central AC & free WiFi with over 1600 sq. ft. of finished living space, 3 bedrooms, 2 full bathrooms, and a large den there is plenty of space for you to relax in with the entire family.    Welcome...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    • Wi-Fi
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at: Seashell Beach Cottage! Beach front vacation rental cottage in Chatham! Stay at this 2 bedroom cottage located right on the beach in Chatham, the best of Cape Cod. Beautiful views! Perfect for a relaxing getaway, this romantic cottage is just steps from the sand, Find your pathway...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to The Cape Escape! Pet Friendly! Walk to Harding's Beach from this Chatham Vacation Rental Home. 4 Bedrooms, sleeps 8. Access to association dock and picnic area in Harding's Hills Association. AC units in 3 bedrooms and the main living area, there is cable and free WiFi too. Calling all...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    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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    2633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Spectacular rental property. This open and airy, 4 bedroom, 4.5 bathroom home offers plenty of living space, inside and out, with it's soaring ceilings, open floor plan, large deck and private backyard. Centrally located in a wonderful neighborhood of high-end homes, this rental includes use of...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Chatham  Cape Cod Waterfront Vacation Rental (6520)1 / 22
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    Just reading the description of this home can't do it justice! The location was perfect for us: high on a bluff overlooking the Sound, so we got lovely breezes even on the few...
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    About this property
    Magnificent views of Bassing Harbor, Ryder's Cove and Pleasant Bay from this 4-bedroom, 3 bathroom waterfront home perched high on a bluff. This home boasts an expansive deck with plenty of outdoor seating for relaxing or dining alfresco and a spacious yard including a stairway leading down to the...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Rosa Rugosa! Walk to Hardings Beach- Central air - private! Ranch-style home with Central air-comfortable, easy living all on one floor! 3 Bedrooms, 2 baths, sleeps 6 with central air, WiFi, and sunroom. Beautiful gardens, patio, yard, and an easy walk to Harding's Beach! Quiet side...
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    02633, Chatham, Cape Cod
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Location Information
    02659, South Chatham, Chatham
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lounge on our beautiful beaches, experience great fishing or spoil yourself in our unique shops all while staying in this charming, remodeled and finely decorated home close to Red River and Pleasant Street Beaches. This home has 4 bedrooms and 3 full baths. There is an en-suite master bedroom...
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    Location Information
    02659, Chatham, Cape Cod
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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