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Holiday Homes and Apartments Cheshire, MA and nearby

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    All 23 Rentals in the Cheshire Area
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    From
    $257
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    1 / 19
    Cheshire
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry

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

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    $385
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    1 / 25
    5 of 5 stars (7) Excellent
    Hancock
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Enquiry
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    $193
    / Night
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    1 / 20
    5 of 5 stars (1) Excellent
    Pittsfield
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
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    $243
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    1 / 16
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
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    Location Information
    Hancock, Berkshires 01237
    4 of 5 stars Reviewed 26 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...
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    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), Alpine Slide (warmer months), Berkshire Express Chairlift to Summit Lodge during ski season. The Berkshire Express provides scenic rides during warmer months. Bentley Brook is situated Slope Side for SKI/IN - SKI/OUT all winter... View all property information
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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 24 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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    $225
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    1 / 9
    5 of 5 stars (12) Excellent
    Lanesboro
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. It is perfect for romantic weekends or family... View all property information
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    Location Information
    Lanesboro, Berkshires 01237
    5 of 5 stars Reviewed 8 July 2014
    We were lucky to happen upon this gem, and highly recommend it to families visiting the area of Mt. Greylock. Great on a rainy day, and interesting for all given the history of...
    5 of 5 stars Reviewed 31 May 2014
    We have stayed in several vacation rentals, and this one was extremely charming. The very first time I saw this one I just knew we had to vacation here while we were in The...
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    $186
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    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    1 Bedroom / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
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    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 17 October 2014
    This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
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    $294
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
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    Location Information
    Hancock, Berkshires 01237
    4 of 5 stars Reviewed 12 August 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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    $289
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    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
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    Location Information
    Hancock, Berkshires 001237
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    $321
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    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Mountain Views
    • Private Fishing...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
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    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 17 August 2014
    The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the...
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    $167
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    1 / 10
    5 of 5 stars (1) Excellent
    North Adams
    2 Bedrooms / 1 Bathroom / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa!!! Animals are welcome is needed. . The master bedroom has an... View all property information
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    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 7 July 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    $128
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    1 / 8
    5 of 5 stars (1) Excellent
    Pittsfield
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    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
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    Location Information
    Pittsfield, Berkshires 01201
    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...
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    $250
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    1 / 12
    4.5 of 5 stars (15) Very good
    New Ashford
    4 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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
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    Location Information
    New Ashford, Berkshires 01237
    5 of 5 stars Reviewed 4 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 2 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...
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    $642
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    1 / 18
    Hinsdale
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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    Location Information
    Hinsdale, Berkshires 01235
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    $308
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    1 / 4
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Housekeeping...
    • Internet Access
    • Mountain Views
    • Ping Pong Table
    • Pool Table
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    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
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    Location Information
    Hancock, Berkshires 01237
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    $180
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    1 / 11
    Hinsdale
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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
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    Location Information
    Hinsdale, Berkshires 01235
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    $321
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    1 / 6
    Hancock
    2 Bedrooms / 1 Bathroom / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
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    Location Information
    Hancock, Berkshires 01237
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    $90
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    1 / 6
    North Adams
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Housekeeping...
    • Internet Access
    • Mountain Views
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    I have a two bedroom apartment and I am renting out the spare bedroom. It is at the end of a dead end street with a huge wooded backyard that includes a grill, picnic table and two fire pits. It is walking distance to Mass MoCA and minutes from downtown Williamstown and/or downtown North Adams. The... View all property information
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    Location Information
    North Adams, Berkshires 01247
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    $1,798
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    1 / 13
    Hancock
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Luxury condo in hancock, ma ....Three bedrooms, loft, 2 baths, living room, kitchen with dining area, a/c, deck w/grill et al, heated pool, tennis court, mountain view. Near williamstown theater, clark art museum, tanglewood and three local golf courses. View all property information
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    Location Information
    Hancock, Berkshires 01237
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    1 / 6
    Savoy
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and... View all property information
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    Location Information
    Savoy, Berkshires 01256
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    1 / 16
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
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    Location Information
    Hancock, Berkshires 01237
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    Windsor
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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
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    Location Information
    Windsor, Berkshires 01270
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    $320
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    1 / 19
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Gym
    • Hot Tub
    • Mountain Views
    • Pool Table
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    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. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback... View all property information
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    Location Information
    Hancock, Berkshires 01237