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Vacation Rentals in Canaan, NY and nearby

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    All 21 Rentals in the Canaan Area
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    From
    $125
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    1 / 9
    Canaan
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry

    The following rentals are within 15 kilometres of Canaan, New York.

    From
    $313
    / Night
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    1 / 19
    5 of 5 stars (15) Excellent
    West Stockbridge, MA
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    travellers have booked this property
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    $188
    / Night
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    1 / 21
    5 of 5 stars (19) Excellent
    Lenox, MA
    4 Bedrooms / 1 Bathroom / Sleeps 7
    travellers have booked this property
    Overview Reviews (19) Make Enquiry
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    $157
    / Night
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge, MA
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Washer
    • Refrigerator
    • Dryer
    • Satellite TV
    • Internet Access
    • Cooker
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    $188
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond, MA
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Water Views
    • Washer
    • Satellite TV
    • DVD Player
    • Internet Access
    • Playground
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
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    Location Information
    Richmond, Berkshires 01254
    From
    $501
    / Night
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    1 / 24
    Lenox, MA
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Sauna
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Playground
    • Shared Indoor Pool
    • Mountain Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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    Location Information
    Lenox, Berkshires 01240
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    $188
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    1 / 14
    5 of 5 stars (1) Excellent
    Ghent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Deck
    • Shared Outdoor Pool...
    • Patio
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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 park-like property it's a beautiful place to vacation. You also have access to a very large swimming pool and the large wooden decks of the main house. The... View all property information
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    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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    $188
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    1 / 20
    5 of 5 stars (1) Excellent
    Pittsfield, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Waterfront
    • Fireplace
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a... View all property information
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    Location Information
    Pittsfield, Berkshires 01201
    5 of 5 stars Reviewed 29 November 2014
    The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived...
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    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Private Fishing...
    • Internet Access
    • Washer
    • Deck
    • Fireplace
    • Mountain Views
    • Dryer
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site at aberkshirehome The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting.... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
    5 of 5 stars Reviewed 25 August 2014
    We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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    From
    $407
    / Night
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    1 / 10
    Richmond, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    In 1832, Josiah Loomis bought a parcel of land 'and the structures thereon', along what was then known as 'Massachusetts Turnpike No. 10,' the toll road between Albany, NY and Hartford, CT. Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years... View all property information
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    Location Information
    Richmond, Berkshires 01254
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    $501
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    1 / 12
    Lenox, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Playground
    • Stereo System
    • Mountain Views
    • DVD Player
    • TV
    • Internet Access
    • Deck
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
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    Location Information
    Lenox, Berkshires 01240
    From
    $249
    / Night
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    1 / 6
    East Chatham
    5 Bedrooms / 3 Bathrooms / Sleeps 15
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This rustic very private property, built in 2011 has sleeping accommodations for up to 15 people in the house. The cedar wood sauna and the grecian inground pool, as well as exquisite main cathedral hall makes the experience one of a kind. We have the following rooms 2 Bedrooms with queen size... View all property information
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    Location Information
    East Chatham, New York 12060
    From
    $376
    / Night
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    1 / 10
    West Stockbridge, MA
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Ping Pong Table
    • Satellite TV
    • Wi-Fi
    • Game Room
    • Swingset
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped.... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    From
    $207
    / Night
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    1 / 10
    East Chatham
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Horse Riding Nearby
    • Watersports Nearby
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • There Are Tennis...
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
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    Location Information
    East Chatham, New York 12060
    From
    $376
    / Night
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    1 / 12
    New Lebanon
    5 Bedrooms / 5 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This home sits on 10 private acres in the beautiful Berkshire mountains. Greeted by friendly wood carved bears, the entire estate consists of a 3 BR main house with 3.5 baths, two bedroom pool house with 1 bath, and 1 bedroom garage apartment with 1 bath. All units are available but this listings... View all property information
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    Location Information
    New Lebanon, New York 12125
    From
    $376
    / Night
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    1 / 13
    Chatham
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Waterfront Antique Farmhouse in the Berkshires with a Barn Gameroom. Our home, a 175 year restored Waterfront antique, is beautifully situated, on a tiered landscape with stone steps and sweeping lawns that border the creek. There are many pocket swimming holes and kayaking, canoeing, and... View all property information
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    Location Information
    Chatham, New York 12184
    From
    $250
    / Night
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    1 / 18
    Austerlitz
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Washer
    • Mountain Views
    • DVD Player
    • Deck
    • Stereo System
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Austerlitz, New York 12017
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    $313
    / Night
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    1 / 14
    Lenox, MA
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    Location Information
    Lenox, Berkshires 01240
    From
    $564
    / Night
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    1 / 20
    Richmond, MA
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Fireplace
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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    Location Information
    Richmond, Berkshires 01254
    From
    $501
    / Night
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    1 / 5
    Old Chatham
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Fireplace
    • Air Conditioning
    • Horse Riding Nearby
    • Waterfront
    • DVD Player
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Old Chatham, New York 12136
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    $125
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    1 / 8
    5 of 5 stars (1) Excellent
    Pittsfield, MA
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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    Location Information
    Pittsfield, Berkshires 01201
    5 of 5 stars Reviewed 3 July 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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