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Holiday Rentals and Homes in Hillsdale, NY

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    1 / 8
    Hillsdale
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 18
    5 of 5 stars (1) Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    1 / 11
    5 of 5 stars (2) Excellent
    Hillsdale
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 26
    5 of 5 stars (7) Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Mountain Views
    • Central Heating
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    About this property
    3 bedrooms, 2 full baths, living room, dining room, kitchen, loft area. Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with heartwarming winter mountain views. The chalet was built in 2003 and has gorgeous stone countertops and two... View all property information
    Location Information
    Hillsdale, New York 12529
    5 of 5 stars Reviewed 21 December 2015
    Owners were delightful to deal with. House was clean and well equipped. Would definitely rent again for a ski weekend! Really enjoyed family dinner at "The Gypsy Joint" in nearby...
    5 of 5 stars Reviewed 8 November 2015
    My family and I spent 4 nights in the chalet. We enjoyed our time there. The chalet is equipped with everything you need. It even has a basement with bycicles, an air hockey...
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    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms... View all property information
    Location Information
    Hillsdale, New York 12529

    The following rentals are within 10 kilometers of Hillsdale, New York.

    1 / 22
    5 of 5 stars (1) Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Balcony
    • Central Heating
    • Waterfront
    • Parking
    • Terrace
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • x
    • x
    About this property
    see better & more photos of property here (copy-paste-edit in browser): tinyurl DOT com/jdjlo3z Elegant and tranquil 2 level lakefront retreat, the perfect escape for any season. 3 bedrooms, 2 bath plus a powder room, gourmet kitchen with island counter, cathedral ceilings, large deck facing lake... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 31 October 2015
    We were delighted to find this attractive cottage on Robinson Pond. We enjoyed watching the ducks and geese out the expansive windows and were so pleased to see no other humans...
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    1 / 14
    5 of 5 stars (1) Excellent
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Parking
    • Air Conditioning
    • DVD Player
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    • Grill
    • Outdoor Dining Area
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    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... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars 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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    1 / 16
    5 of 5 stars (4) Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7) BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS. This three bedroom , two living rooms with flate screen home theater system, 2 Baths, plus sleeping loft(or office) has it all. Our deeded lake access on a clean freshwater lake... View all property information
    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed 6 January 2015
    I'm sorry for not responding sooner. Your home was the best vacation rental in which I have stayed today and I rent frequently in the Berkshires. I am going to want to stay there...
    5 of 5 stars Reviewed 20 October 2014
    We spent seven days at this house in the New York side of the Berkshires. I'd never rented in this way before so I was a little nervous. When we got there, we were really wowed...
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    Craryville
    2 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Grill
    • Hot Tub
    • Private Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    You won't see another property like this. This is no ordinary barn. As you step inside you are greeted by a custom made dining room table that comfortably sits 16-20 people! Sit back and watch the deer/turkey/pheasant go by your window. Experience full upscale luxury in a beautifully restored and... View all property information
    Location Information
    Craryville, New York 12529
    1 / 19
    5 of 5 stars (1) Excellent
    North Egremont, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    1 / 6
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher Beds: 1 Queen Bed, 4 Twin Beds View all property information
    Location Information
    Copake, New York 12529
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
    • Grill
    • Skiing: Property Is...
    • DVD Player
    • Parking
    • Patio
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This house had extensive renovations in 2014 and has free wifi throughout. The kitchen and living room were combined for a large open family area. The kitchen was completely renovated with high end cabinets, granite countertops, a huge center island that seats five, and a beautiful large mission... View all property information
    Location Information
    Copake, New York 12521
    Copake Falls
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ski the Berkshires at Catamount 10 minutes away and Butternut 30 minutes away. Beautifully renovated cottage in walking distance to Taconic State Park. Enjoy farm to table dining nearby. Hike to Birkshires' Bash Bish Falls, bike on the Harlem Valley Bike Trail, and swim in the spring fed iron ore... View all property information
    Location Information
    Copake Falls, New York 12517
    1 / 15
    5 of 5 stars (7) Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
    • Air Conditioning
    • Porch
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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,... View all property information
    Location Information
    Copake, New York 12516
    4 of 5 stars Reviewed 10 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 area...
    5 of 5 stars 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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    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
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
    Location Information
    Copake, New York 12516
    1 / 4
    4 of 5 stars (1) Very good
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
    • Porch
    • DVD Player
    • Washer
    • Grill
    • Central Heating
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
    Location Information
    Copake, New York 12529
    4 of 5 stars Reviewed 14 November 2012
    My husband and I drove up from NYC and stayed here for a weekend in april. The lake community was just waking up for spring and we loved the feeling of getting away from it all...
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    1 / 9
    Copake
    4 Bedrooms, 3 Bathrooms, Sleeps 17 | Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • Grill
    • DVD Player
    • Central Heating
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Completely furnished kitchen, bedrooms and bathrooms. Master bedroom has full bath, large window overlooking lake, secondary bedroom has 1/2 bath. Downstairs area, has two curtained rooms with king beds, two bunk beds and a 1/2 bath. Dock on property gives access to lake within 30 feet of house,... View all property information
    Location Information
    Copake, New York 12516
    1 / 50
    5 of 5 stars (7) Excellent
    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed 7 October 2015
    My husband and I were looking for a relaxing getaway for a long weekend. We chose the River Song and were not disappointed. The suite is beautifully and comfortably furnished...
    5 of 5 stars Reviewed 9 July 2015
    This suite is located in a beautiful serene setting. Barbara keeps the suite very clean, and her attention to every detail is unmatched. We had a wonderful stay, and only wish...
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