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Vacation Rentals in Chatham, NY and nearby

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    1 / 14
    Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 48
    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    The following rentals are within 15 kilometres of Chatham, New York.

    1 / 19
    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 5
    Old Chatham
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Old Chatham, New York 12136
    1 / 19
    5 of 5 stars (1) Excellent
    Canaan
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Terrace
    • Grill
    • DVD Player
    • Parking
    • Central Heating
    • Mountain Views
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Mountain Top Custom Built Post + Beam Home Highest Point in Columbia County - Mercer Mountain 2500 Sq Ft Home with Incredible Views and Sunsets Large 1000 Sq Ft Deck - Privacy - 6.25 Acres Hand Cut Beams from Nova Scotia with Stone Throughout Ist Floor Master Suite - 2 Bedrooms on 2nd Floor - Loft... View all property information
    Location Information
    Canaan, New York 12060
    1 / 16
    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
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Columbiaville, New York 12534
    1 / 25
    4.5 of 5 stars (3) Very good
    Valatie
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Porch
    • Satellite TV
    • Patio
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Valatie, New York 12184
    1 / 18
    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
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Austerlitz, New York 12017
    1 / 13
    5 of 5 stars (1) Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Ghent, New York 12075
    5 of 5 stars 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 full...
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    1 / 14
    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Parking
    • Patio
    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Spencertown, New York 12165
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    1 / 16
    Nassau
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Nassau, New York 12123
    1 / 5
    5 of 5 stars (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
    • Child-friendly
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Old Chatham, New York 12136
    5 of 5 stars 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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    1 / 19
    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Philmont, New York 12534
    1 / 1
    Valatie
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Porch
    • Waterfront
    • DVD Player
    • Patio
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Homey A frame house filled with multiple items and family pictures collected over the years and during trips primarily to Africa and Asia. Directly on Kinderhook Lake in Town of Chatham, off private road with three other homes. Good for swimming and fishing. Halfway between Hudson with its... View all property information
    Location Information
    Valatie, New York 12184
    1 / 10
    East Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • DVD Player
    • Patio
    • Mountain Views
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our cottage has been lovingly maintained and is in pristine condition. It is also very well laid out. You will enter through a generous foyer with closet and antique breakfront, and pass the media room (optional 3rd bedroom) with a divided light glass wall separating it from the family room. The... View all property information
    Location Information
    East Chatham, New York 12060
    1 / 9
    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
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Canaan, New York 12029