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Chatham Vacation Rentals

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    Don't let other travellers get your favourite Chatham area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 15 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.
    Mountain Top - Post + Beam House1 / 19
    (2)Excellent
    Canaan
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Columbiaville
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Philmont, New York 12534
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Haddock Hill House1 / 5
    (1)Excellent
    Old Chatham
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 September 2016
    We cannot say enough about how wonderful the property and the Owner are. Modern and well appointed, this property is beyond expectations. Private and immaculate, much time and...
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    About this property
    Beautiful suite in a gorgeous county home in the Berkshires. Private entrance and your own courtyard with garden views. Large comfortable bed with plenty of pillows and luxurious spa- style bathroom. Close to Tanglewood, Jacobs Pillow, Kripalu, Great Barrington, and Hudson. Hiking, biking, and...
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    Location Information
    Old Chatham, New York 12136
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Amenities & Details
    • Porch
    • Satellite TV
    • Patio
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning New Lakefront Home Near Berkshires with Gourmet Kitchen, large expansive views of Kinderhook Lake. All the bells and whistles including a TV in the Master Bathroom and a whole house stereo system. This home is an air conditioned, upscale Craftsman- styled cottage with 75 feet of lakefront...
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    Valatie, New York 12184
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Patio
    • 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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    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Location Information
    Ghent, New York 12075
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Hudson Valley Cottage1 / 13
    (1)Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 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.<BR><BR>The bedroom and...
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    Location Information
    Ghent, New York 12075
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Austerlitz
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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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    Location Information
    Austerlitz, New York 12017
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Austerlitz, New York 12017
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Kinderhook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    nesteldown pet friendly1 / 5
    (1)Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Grill
    • Waterfront
    • Patio
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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.<BR>Gated , 4BR Elegant Colonial Estate on Pristine River/stream in most desirable area in Columbia County.<BR>Set in sleepy upscale Historic Hamlet on Park-like grounds.<BR>Bordered by over 150 acres of fields with Sunset views.<BR>The best Swimming , fantastic Fishing,...
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    Location Information
    Old Chatham, New York 12136
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Canaan
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Canaan, New York 12029
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Nassau
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Understated Post and Beam house on a private bluff with views of the Catskills. Elicits calm and pleasure on approach and entry. The house sits on 23 acres of open fields and wooded trails on a road (known locally for its beauty) with ponds and horse farm. The house has cathedral ceilings on both...
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    Location Information
    Nassau, New York 12123
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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