We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Elder Access Holiday Rentals in Cheshire, MA

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price range
    (€206 Average)
    €0per night €1,000+
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...

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

    From
    €129
    / Night
    Payment Protection
    View Details
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6
    other travellers have booked this property
    Overview Reviews (2)
    Overview Reviews (2)
    From
    €204
    / Night
    Payment Protection
    View Details
    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other travellers have booked this property
    Overview Reviews (1)
    Overview Reviews (1)
    From
    €446
    / Night
    Payment Protection
    View Details
    Hinsdale
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview
    Overview
    From
    €201
    / Night
    Payment Protection
    View Details
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview
    Overview
    Amenities & Details
    • Hot Tub
    • Sauna
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 01237
    From
    €168
    / Night
    Payment Protection
    View Details
    1 / 16
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travellers have booked this property
    Overview Reviews (1)
    Overview Reviews (1)
    Amenities & Details
    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
    Location Information
    Hancock, Berkshires 01237
    4 of 5 stars Reviewed 25 October 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
    See all reviews
    From
    €125
    / Night
    Payment Protection
    View Details
    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travellers have booked this property
    Overview
    Overview
    Amenities & Details
    • Central Heating
    • TV
    • DVD Player
    • Stereo System
    • Internet Access
    • Deck
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 01235
    From
    €669
    / Night
    Payment Protection
    View Details
    Stephentown, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 16
    Overview
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This ultra-private ski ranch is situated on 52-wooded acres and is located one quarter mile from NY Route 22 in Rennselaer County just 10 minutes from the Massachusetts boarder and 20 minutes from the Vermont border. Several ski areas are accessible from the house including Jiminy Peak, Bosquet... View all property information
    Location Information
    Stephentown, New York 12168
    From
    €267
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (2) Excellent
    Stephentown, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (2)
    Overview Reviews (2)
    Amenities & Details
    • Washer
    • Mountain Views
    • Wi-Fi
    • Horse Riding Nearby
    • TV
    • Dryer
    • Deck
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 500 square foot grand room for parties,... View all property information
    Location Information
    Stephentown, New York 12168
    5 of 5 stars Reviewed 23 July 2015
    I signed up on trip advisor just to say thank you and awesome job! I travel between New York and Boston quite a bit on business, I adore detouring into the Berkshires for a day...
    5 of 5 stars Reviewed 13 July 2015
    We attended a small function at BBLODGE a few weeks ago and it was simply delightful. The weather was lovely so we sat on the deck which overlooks the Berkshire mountains...
    See all reviews
    From
    €156
    / Night
    Payment Protection
    View Details
    Windsor
    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
    Location Information
    Windsor, Berkshires 01270
    From
    €241
    / Night
    Payment Protection
    View Details
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview
    Overview
    Amenities & Details
    • Housekeeping...
    • Game Room
    • Shared Indoor Pool
    • Air Conditioning
    • Sauna
    • Wi-Fi
    • Ping Pong Table
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Exclusive Deal for Christmas week, the most wanted week of the year! Ski-In/Ski-Out Plus Year-Round Mountainside Fun! Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. During the winter, ski out your... View all property information
    Location Information
    Hancock, Berkshires 01237
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    €3,476
    / Month
    Payment Protection
    View Details
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview
    Overview
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Private Outdoor...
    • Satellite TV
    • Private Tennis Court
    • Sauna
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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. Sledding on back terrace. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and... View all property information
    Location Information
    Hancock, Berkshires 01237
    From
    €267
    / Night
    View Details
    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (9)
    Overview Reviews (9)
    Amenities & Details
    • Skiing: Property Is...
    • Air Conditioning
    • Satellite TV
    • There Are Tennis...
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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 01237
    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...
    See all reviews
    From
    €156
    / Night
    View Details
    1 / 12
    4.5 of 5 stars (15) Very good
    New Ashford
    4 Bedrooms, 3 Bathrooms, Sleeps 7
    Overview Reviews (15)
    Overview Reviews (15)
    Amenities & Details
    • Wi-Fi
    • Private Fishing...
    • Central Heating
    • Mountain Views
    • Water Views
    • Housekeeping...
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Berkshire Gorge House sits beside the Green River above a turbulent set of cascades, on the western slopes of Mt. Greylock. This 5-bedroom house was built in 1910 by New England's finest craftsmen. It has been recently remodeled and is offered for rent. The house offers a new kitchen with gas... View all property information
    Location Information
    New Ashford, Berkshires 01237
    5 of 5 stars Reviewed 3 January 2015
    I am kicking myself that I didn't invite my brother, sister-in-law and their small kids to come with us on this trip. There sure was plenty of room! Right when you enter the...
    5 of 5 stars Reviewed 1 December 2014
    The house was everything we expected. Right from the beginning there was clear communication between us, the owner and the property manager. The booking process was easy. Checking...
    See all reviews
    From
    €89
    / Night
    View Details
    1 / 8
    4 of 5 stars (2) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 5
    Overview Reviews (2)
    Overview Reviews (2)
    Amenities & Details
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
    Location Information
    Pittsfield, Berkshires 01201
    3 of 5 stars Reviewed 18 August 2015
    The place was less than ideal in that the room smelled of smoke when we walked in. The bedroom had no windows and that felt very claustrophobic. It did have a kitchen which was...
    5 of 5 stars Reviewed 3 July 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
    See all reviews