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Canaan House Rentals

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    Don't let other travellers get your favourite Canaan area holiday rental. You're so close to securing your perfect getaway. Book today.
    21 Matching Rentals in the Canaan AreaView all 34 rentals
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    The following rentals are within 15 kilometers of Canaan.
    Great Vacation House in the Berkshires on Richmond Pond1 / 10
    (4)Excellent
    Richmond, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    West Stockbridge, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Heart of Lenox1 / 10
    (2)Excellent
    Lenox, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Two weeks in July !!!  Last minute cancellation  WOW1 / 18
    (7)Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed 27 August 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination, a haven, a state...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Heart of the Berkshires!1 / 12
    (2)Very good
    Lenox, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    A friend and I rented this charming home for 3 nights. It was immaculate, the kitchen was well stocked, furniture/beds comfortable. The bedrooms had window a/c units. What...
    Reviewed 29 June 2017
    I was looking for a place for two couples for a weekend in the Berkshires, and stayed at this house. It was a perfect fit for my needs. The house is on a road that has very...
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    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest...
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    Lenox, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Berkshire Country Estate - The Library Suite1 / 21
    (1)Excellent
    Old Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 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
    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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    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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    Austerlitz, New York 12017
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pittsfield, MA
    7 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Terrace
    • Washer
    • Balcony
    • Patio
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful 7 bedroom home with over 4000 sq. ft. of nicely furnished large rooms. Nestled in the heart of the Berkshire Mountains, between 2 lakes and located in a quiet family friendly neighborhood. Just minutes from the New York border. Our home is a fantastic deal for the wonderfully...
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    Location Information
    Pittsfield, Berkshires 01201
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 18
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    Richmond, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Richmond, Berkshires 01254
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    NEW! 'Butterfly Hill' 2BR West Stockbridge House1 / 24
    (1)Excellent
    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    We thoroughly enjoyed our week at Butterfly Hill. It was near Tanglewood, our main reason for the visit, and all the nearby towns where we found good restaurants and shops. We...
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    About this property
    Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provide the perfect...
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    Location Information
    West Stockbridge, Berkshires 01266
    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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    Location Information
    Old Chatham, New York 12136
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 16
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    Richmond, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation home has something for everyone! If you're a culture vulture, outdoor enthusiast, or just want the peace and quiet of the country, this 4 bedroom home in the Berkshires is for you! It is 15 minutes from Lenox and Tanglewood, 10 minutes from shopping, restaurants and several theatres,...
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    Location Information
    Richmond, Berkshires 01254
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stephentown
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two story cape that can sleep up to 12 people on 50 acres. Fully equipped kitchen, laundry area and dining & living room that faces the Berkshire Mountains. Relaxingy deck with barbecue. Walking trails and swimming pond make it a perfect getaway place. Wifi, a/c tv Near all Berkshire attractions,...
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    Stephentown, New York 12168
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy cottage is perfect for a small group of friends or a family getaway in the beautiful Berkshires. We're on 120 acres of private woods but only 7 miles from Jiminy Peak. The main space features a cathedral ceiling in the open living/dining area, with a glass-front woodstove for chilly...
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    Location Information
    Stephentown, New York 12168
    Holiday Rental House - 3 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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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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    Spencertown, New York 12165
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lenox, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No matter the season, you'll find the getaway you crave while staying at this 3-bed, 2.5-bath house in Lenox! This welcoming vacation rental features room for 6, numerous amenities, and an incredible location just minutes from the Tanglewood Music Center. In addition, enjoy easy access to the...
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    Location Information
    Lenox, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lenox, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy leisurely lakeside days just a walk away as you stay at this 3-bed, 1.5-bath vacation rental house that sleeps 6 in Stockbridge! With mossy grounds below and age-old oaks towering above, this cozy cottage is a dreamy retreat, perfect for those looking for a bit of the great outdoors without...
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    Location Information
    Lenox, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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