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Holiday Homes in Chatham

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    Don't let other travellers get your favourite Chatham area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in Chatham
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    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 15 kilometres of Chatham.
    Stuyvesant
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Stunning New Construction All SeasonLakefront Home1 / 25
    (3)Very good
    Valatie
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be enjoying a newly renovated space with Calcutta marble floors throughout. The house features 2 bedrooms at opposite sides of the house to provide more privacy. A luxurious bathroom with a Roman soaking tub and marble mosaics. A totally loaded kitchen and great outdoor space which...
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    Ghent, New York 12075
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Austerlitz
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Hot Tub
    • Central Heating
    • Balcony
    • Grill
    • Patio
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beautiful renovated Georgian Colonial home sits amongst 40 acres of natural beauty. The house overlooks a serene pond and all its beauty with views of natural forrest beyond. The house itself has a oversized chef's eat in kitchen. The Kitchen has all the amenities to host wonderful meals and...
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    Austerlitz, New York 12017
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Berkshire Country Estate - The Library Suite1 / 21
    (1)Excellent
    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We were looking for a one night stay while in the neighbourhood. We could not have asked for a better place. This amazing house will take you away from everyday business and...
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    About this property
    The beautiful Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires, minutes from Lenox MA & Hudson NY, less than a 2 1/2 drive from New York City. Library Suite: Luxuriate in our spacious two room suite to accommodate 2-4 guests with fireplace, full bath w/ deep soak...
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    Location Information
    Old Chatham, New York 12136
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Parking
    • Shared Garden
    • Internet Access
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes...
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    Austerlitz, New York 12017
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hudson Valley Cottage1 / 13
    (1)Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2013
    This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads...
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    About this property
    Enjoy a newly renovated and furnished, one bedroom guest cottage, in an enchanting and quiet area. Located behind a stone castle on a 2 1/2 acre park-like property it's a beautiful place to vacation. You also have access to a large 6 person hot tub and all the deck areas. The bedroom and living...
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    Ghent, New York 12075
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Columbiaville
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Grill
    • Balcony
    • Porch
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Complete renovation with privacy. This rural mill worker's cottage has been upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a private paved road. Minutes to Hudson and Kinderhook, NY. This 1400 sf home is on three levels with laundry in...
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    Location Information
    Columbiaville, New York 12534
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the center of Columbia County, NY this retreat is a great spring board to all it has to offer: minutes to Hudson, Chatham, High Falls, hiking trails, farms, streams. You’ll love the varied bright cozy rooms to lounge in, including a screened front porch. Most relaxing is to hang out on...
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    Location Information
    Philmont, New York 12534
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kinderhook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located for your next Hudson Valley Wine Tour or Relaxing Hudson Valley Bed and Breakfast Hotel Lodging Get-a-way with an Organic Farm to Table Breakfast! Mile Hill B and B, c.1852, is an original jewel with an interesting history. This is a newly renovated Colonial Farm House; two...
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    Location Information
    Kinderhook, New York 12106
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Old Chatham
    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires, only 2 1/2 hours from New York City and Boston. Surrounded by the beauty of the Berkshires, the estate is very private, with a 1/8 mile driveway leading to the 10 acre front lawn. A large elegant, yet...
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    Old Chatham, New York 12136
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 16
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    Malden Bridge
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Terrace
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is surrounded by 40 acres of sprawling meadows and wood.2 1/2 hours from NYC and Boston, and 3 to Montreal Arts scene, with Ellsworth Kelly and Marina Abramovic also, and a lot of younger NYC artists relocating nearby much in the way that the 50s artists sought out the space of the...
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    Location Information
    Malden Bridge, New York 12123
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Valatie
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ready for a summer vacation? Relax next to the creek with family and friends, fantastic view. You can prepare delicious meal in the gourmet kitchen. Recently renovated light filled home situated on a beautiful and relaxing 11 acres with creek frontage. Only 10 min from many great local restaurants...
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    Location Information
    Valatie, New York 12184
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on 60 acres in the foothills of the Berkshires, minutes from Lenox MA & Hudson NY, less than a 2 1/2 drive from New York City. It is an elegant, yet comfortable family Georgian estate, privately sited with a long driveway and a 10 acre front lawn. Luxuriate in the Rose Suite, a nearly 1,100...
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    Location Information
    Old Chatham, New York 12136
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Canaan
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Balcony
    • Air Conditioning
    • Grill
    • Outdoor Dining Area
    • Porch
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A cute cabin in the woods with easy access to a lake a short 500 ft walk down a dirt road. Swimming is available at a private member beach by either canoe or a sort drive to the other end of the the Lake. Convenient to the Berkshires. Tanglewood is a 15 min drive and Jacob's Pillow and Saratoga...
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    Canaan, New York 12029
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    nesteldown pet friendly1 / 5
    (1)Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 November 2015
    This was such a great place for us to stay , it had everything , even went fishing - biking , the house was just perfect , we even had friends over and we had plenty of room...
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    About this property
    'One of a kind' listing. Gated , 4BR Elegant Colonial Estate on Pristine River/stream in most desirable area in Columbia County. Set in sleepy upscale Historic Hamlet on Park-like grounds. Bordered by over 150 acres of fields with Sunset views. The best Swimming , fantastic Fishing, stone Campfire...
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    Location Information
    Old Chatham, New York 12136
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Frank Lloyd Wright-inspired retreat is the perfect country escape for city dwellers. Set on 30 private acres with trails for hiking and a lake, this professionally decorated home blends rustic charm with modernity. There are two bedrooms, one with a fireplace, two bathrooms, plus a sleeping...
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    Location Information
    Spencertown, New York 12165
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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