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Hillsdale Holiday Rentals

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    Beautifully decorated & immaculate log chalet1 / 26
    (14)Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Overnight at Althouse -Higgins1 / 11
    (3)Excellent
    Hillsdale
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Hillhouse Log Cabin1 / 18
    (1)Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Hillsdale
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    Smoking allowed
    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...
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    Location Information
    Hillsdale, New York 12529
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Hillsdale
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Internet Access
    • Satellite TV
    • Central Heating
    • Washer
    • Outdoor Dining Area
    • Balcony
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Glorious views across meadows to distant mountains. Open-plan living/dining/kitchen with fireplace, and soaring ceiling. Many glass doors lead to decks where you may drink in the view. Great master bedroom suite with state of the art bathroom, two guest rooms, family room, media room and two guest...
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    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 10
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    Hillsdale
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Parking
    • Balcony
    • Patio
    • Washer
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    Pet friendly
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    Smoking allowed
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    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Hillsdale
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Hillsdale, New York 12529
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Hillsdale
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
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    Pet friendly
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    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Hillsdale
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • Internet Access
    • Balcony
    • Terrace
    • DVD Player
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Hillsdale
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
    • Washer
    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Hillsdale, New York 12529 5048
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
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    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hillsdale
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Patio
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    Pet friendly
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    Location Information
    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Washer
    • Balcony
    • Patio
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hillsdale
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
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    Hillsdale, New York 12529
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Hillsdale
    7 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
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    Smoking allowed
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    Location Information
    Hillsdale, New York 12529
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 8
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    Hillsdale
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Patio
    • Washer
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
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    Smoking allowed
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    Location Information
    Hillsdale, New York 12529
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Hillsdale
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Hillsdale, New York 12517
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Hillsdale
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Internet Access
    • Parking
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Hillsdale, New York 12529
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hillsdale
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Hillsdale, New York 12592
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Patio
    • Shared Indoor Pool
    • Housekeeping Included
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Hillsdale, New York 12529
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hillsdale
    6 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Hillsdale, New York 12517
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 10
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    The following rentals are within 10 kilometres of Hillsdale.
    Copake Falls
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Copake Falls, New York 12517
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Copake Lakeview Ranch1 / 26
    (2)Excellent
    Copake
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Mountain Views
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2016
    Fantastic place to unwind and reconnect with nature: huge oak trees frame the view of the lake & mountains in the distance. Birds, wind, and occasional fish splashing in...
    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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    About this property
    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 and spectacular Taconic mountain range + small screened porch. Breathtaking lake and mountain...
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    Location Information
    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Berkshire Barn Paradise1 / 23
    (1)Excellent
    Craryville
    2 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Grill
    • Hot Tub
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2016
    The pictures and description don't do this place justice! There are no details left undone - Joe, our host, has thought of everything. The home was beautiful and FULLY stocked...
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    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...
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    Location Information
    Craryville, New York 12529
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 8
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    Newly Renovated Lakefront Getaway on Robinson Pond1 / 14
    (1)Excellent
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    • Outdoor Dining Area
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 6
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    Outdoor getaway hunting,fishing,skiing..relaxation1 / 15
    (8)Excellent
    Copake
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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, 3 Bathrooms, Sleeps 9
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    RiverSong Suite In The Berkshires1 / 52
    (10)Excellent
    North Egremont, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Certificate of Excellence
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    I was very skeptical about staying somewhere other than a "chain hotel or resort". That is until I met Barbara and Phil. They were a very gracious, humble and warm...
    Reviewed 16 November 2016
    River Song is a wonderfully private and relaxing place to hang your hat before heading out to visit Great Barrington and all the beauty that the Berkshires offers in any season...
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    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>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,...
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    Location Information
    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Copake
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Grill
    • Washer
    • Internet Access
    • DVD Player
    • Parking
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note that rates listed and minimum days to rent are for standard nights. Please contact owner for rates during prime dates (e.g., summer when pool is open and holidays). This house had extensive renovations in 2014 and has free wifi throughout. The kitchen and living room were combined for...
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    Location Information
    Copake, New York 12521
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Lake House in the Berkshires1 / 19
    (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
    Kid friendly
    Smoking allowed
    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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    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...
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    Location Information
    North Egremont, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Waterfront
    • Porch
    • DVD Player
    • Washer
    • Grill
    • Central Heating
    • 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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    TAKE ME HOME, COUNTRY ROADS1 / 16
    (4)Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7)<BR><BR>BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS.<BR><BR>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...
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    Location Information
    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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