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Hillsdale House Rentals

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    Don't let other travellers get your favourite Hillsdale area holiday home. You're so close to securing your perfect getaway. Book today.
    24 Matching Rentals in the Hillsdale AreaView all 46 rentals
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    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    The following rentals are within 15 kilometres of Hillsdale.
    Country Elegance in the Berkshires1 / 22
    (2)Excellent
    Great Barrington, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.1 / 18
    (7)Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 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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    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    We had a large group staying at the house with kids and had a great experience. Elaine is very thoughtful, helpful and attentive. She obviously cares about the house and makes...
    Reviewed 14 November 2017
    Elaine was a pleasure to communicate with and made us feel right at home. The home is just how it looks in the pictures. If you're searching for a comfortable, clean, and cozy...
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    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
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    Location Information
    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 34
    (4)Very good
    Great Barrington, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed 16 November 2017
    We rented this lovely home on the lake (or maybe it's a pond... Long Pond I think) last year and loved every minute of our visit. The house is well equipped and has all one...
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    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Shaker Hill1 / 27
    (2)Average
    Great Barrington, MA
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    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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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    Great Barrington, MA
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2018
    This home is a wonderfully appointed home, conveniently located just outside of town. It was perfect for our multiple family ski getaway. The owner is thorough in helping...
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    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another....
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Newly Renovated Lakefront Getaway on Robinson Pond1 / 14
    (2)Excellent
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Central Heating
    • Wi-Fi
    • Private Garden
    • Grill
    • DVD Player
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    I just spent three nights enjoying Ilana’s house on Robinson Pond.Fishing and swimming in the lake.Eating and enjoying cocktails on her beautiful deck.Everything was really nice...
    Reviewed 6 February 2014
    The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
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    About this property
    Beautifully restored 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutted the house completely incorporating modern amenities like a brand new stainless steel kitchen with granite countertops, hardwood bamboo flooring and a large deck to...
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    Location Information
    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    'Butterfly Hill' West Stockbridge Home on 3 Acres!1 / 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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    Outdoor getaway hunting,fishing,skiing..relaxation1 / 17
    (8)Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2015
    Comfortable, well equipped house that's ideal for a family or group of friends outing. Roomy with yard, deck and BBQ. Close to Copake, the local lake and the sights of the...
    Reviewed 5 September 2014
    a great location tucked away yet close to all activities. The house is super comfortable and clean. Includes everything you might want, wifi internet is free and easy to access
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    About this property
    Rustic 3 Bedrooms vacation home 1500 sq ft sleeps 9+ There are 6 beds (1 queen bed, 3 single beds (two beds have a trundle bed underneath) and 1 double sofa-bed, a pack & play and high chair for the little one! Full kitchen, 2 baths and large living and dining space. Wrap around deck, BBQ grill,...
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    Location Information
    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Great Barrington, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In 2016 Smithsonian Magazine deemed Great Barrington, 'The Best Small Town in America.' Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood. Manor Lane...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Great Barrington, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Terrace
    • Balcony
    • Housekeeping Included
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded high on a mountainside and surrounded by thousands of acres of state park and conservation land, The Pod is a rustic early 1970's timber and glass octagon set on a concrete pedestal. Decks on four sides with forest or distant mountain views. One stream runs within 15 feet of the master...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    North Egremont, MA
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book a one-of-a-kind stay in this 5-bedroom, 4.5-bathroom vacation rental home in South Egremont. Built from the bones of a 15th-century British barn, this 4,000-square-foot home for 10 is one of the oldest structures in Massachusetts! Whether you were drawn to the Berkshires by the natural beauty...
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    Location Information
    North Egremont, Berkshires 01258
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    Cozy and clean in Gt Barrington- available for October1 / 14
    (1)Very good
    Great Barrington, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Porch
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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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    Location Information
    Philmont, New York 12534
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Great Barrington, MA
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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    Cozy  Copake Lake Cottage1 / 4
    (1)Very good
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Porch
    • DVD Player
    • Washer
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage with a view of Copake Lake has 3 bedrooms and a loft. The master bedroom contains a queen bed, a second bedroom contains a double bed, and the third bedroom contains two bunk beds. The recently-renovated bathroom has a washer/dryer and a whirlpool tub. There is also a sunroom and the...
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    Location Information
    Copake, New York 12529
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Craryville
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1860s FARMHOUSE WITH CHARM AND MODERN UPDATES. COME SPEND THE WINTER IN THE COUNTRY! CLOSE TO GREAT DINING, SHOPPING AND SKIING. Ask about our discounts for multi-week and monthly stays! Business ready: self check-in, wireless internet, wireless printing An Idyllic Country Escape 2 Hours from...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Terrace
    • Washer
    • Balcony
    • Central Heating
    • Patio
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A single storey house with a large basement less than 100 yards from the boat launch to the lake. Swimming, fishing, boating, walking, climbing, cycling and skiing all within 20 minutes ride from the house. A perfect location for all of these activities, plus a quiet location if you just want to...
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    Location Information
    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Craryville
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Grill
    • DVD Player
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house is in Columbia County, Less than 2 hours from NYC. 5 bedrooms and gorgeous dining room. Can sleep up to 12 people comfortably. The house is surrounded by 9 acres of beautiful land with a creek on the property. Located in the beautiful Columbia County. Nearby the town of Hudson. 10...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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