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Old Chatham Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite Old Chatham area vacation rental. You're so close to securing your perfect getaway. Book today.
    13 Matching Rentals in the Old Chatham AreaView all 15 rentals
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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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    nesteldown pet friendly1 / 5
    (1)Excellent
    Old Chatham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Old Chatham
    8 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 10 miles of Old Chatham.
    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
    • Cable/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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    Austerlitz
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Parking
    • Shared Yard
    • 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Kinderhook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Private Yard
    • 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, 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
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 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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    Location Information
    Ghent, New York 12075
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Valatie
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • Housekeeping Included
    • Balcony
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated 1800s farm house on 100 acres with heated in ground gunnite pool, hiking trails located on a beautiful creek. We also have a guest house with two more bedrooms and a full kitchen by the pool that is perfect for bringing your in-laws or babysitter. The house has a chef's kitchen...
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    Location Information
    Chatham, New York 12037
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    Old Chatham Flight and Weather Info
    Airports nearby (1)
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    ALB
    Albany Intl Airport
    24.3 miles from Old Chatham
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