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Elder Access Holiday Rentals in Hillsdale

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    $342 Average
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    Don't let other travellers get your favourite Hillsdale area holiday rental. You're so close to securing your perfect getaway. Book today.
    19 Matching Rentals in the Hillsdale AreaView all 42 rentals
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    Beautifully decorated & immaculate log chalet1 / 26
    (15)Excellent
    Hillsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 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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    The following rentals are within 15 kilometres of Hillsdale.
    Berkshires: Romantic Cottage with spectacular view1 / 13
    (22)Excellent
    Great Barrington, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Berkshire Farmhouse Vacation1 / 20
    (35)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 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...
    Reviewed 3 October 2017
    My family and myself enjoyed our stay at Elaine's rental home. There are many things to do in the area; hiking, shopping, biking, just to name a few. We all had a great time...
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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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    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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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (3)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
    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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    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 room, fall foliage and scenic atmosphere in the area, and soak in the...
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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    Great Barrington, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Internet Access
    • 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 17 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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    Location Information
    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Newly Renovated Lakefront Getaway on Robinson Pond1 / 28
    (1)Excellent
    Copake
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    Lake House in the Berkshires1 / 19
    (1)Excellent
    North Egremont, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    Alford, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2017
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
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    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath...
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    Location Information
    Alford, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    TAKE ME HOME, COUNTRY ROADS, Beautiful homeWith Private Lake Access1 / 16
    (4)Excellent
    Copake
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    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) 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...
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    Location Information
    Copake, New York 12516
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
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    Location Information
    West Stockbridge, Berkshires 01266
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    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
    • 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, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Balcony
    • Terrace
    • DVD Player
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely refurbished 1827 post and beam Barn renovated July 2012 featuring an Adirondack 'chic' style. Appointed with Mitchell Gold furniture, a custom built 6' round dining room table, indoor fireplace (Dec 2013), double insulated windows, concrete counter-tops and island/bar, stainless...
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    Location Information
    Craryville, New York 12521
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 14
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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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