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Elder Access Holiday Rentals in Cheshire, MA and nearby

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    The following rentals are within 15 kilometres of Cheshire, Massachusetts.

    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 16
    4.5 of 5 stars (2) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 11
    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Central Heating
    • DVD Player
    • Washer
    • Balcony
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
    Location Information
    Hinsdale, Berkshires
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
    Location Information
    Hancock, Berkshires
    5 of 5 stars Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    1 / 13
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor... View all property information
    Location Information
    Hancock, Berkshires
    1 / 24
    5 of 5 stars (6) Excellent
    Stephentown, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Parking
    • Mountain Views
    • Wi-Fi
    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Countryside setting with a fantastic view of the Berkshires and centrally located. 10 minutes to Jiminy Peak ski area, 30 minutes to Tanglewood, 25 minutes to Stockbridge, 20 minutes to Mt. Greylock, 25 minutes to Williamstown theater. the lodge has a 400 square foot grand room for parties,... View all property information
    Location Information
    Stephentown, New York
    5 of 5 stars Reviewed 1 week ago
    My siblings and I (8 adults total) spent a wonderful weekend at the Blueberry Lodge. Most of our time was spent at the lodge except for an afternoon and evening attending the...
    5 of 5 stars Reviewed 8 March 2016
    My girlfriends and I have been going on yearly ski trips primarily in NH, VT, and ME for the past 29 years. This year we decided to try the Berkshires, for some place different...
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    1 / 14
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    ***AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. RATES ARE SUBJECT TO CHANGE UNTIL RESERVATION IS CONFIRMED*** Bentley Brook, located in the Jiminy Peak ski area, offers a variety of on-site amenities -- from downhill skiing to swimming and biking. The Berkshire area also provides a vast array of... View all property information
    Location Information
    Hancock, Berkshires
    1 / 21
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Skiing: Property Is...
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook... View all property information
    Location Information
    Hancock, Berkshires
    5 of 5 stars Reviewed 23 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    4 of 5 stars Reviewed 27 January 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
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    1 / 14
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
    Location Information
    Hancock, Berkshires
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    1 / 31
    Pittsfield
    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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Pittsfield, Berkshires