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Cheshire Elder Access Vacation Rentals

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    Don't let other travellers get your favourite Cheshire area vacation rental. You're so close to securing your perfect getaway. Book today.
    19 Matching Rentals in the Cheshire AreaView all 36 rentals
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    The following rentals are within 15 kilometres of Cheshire.
    Wyndham Bentley Brook at Jiminy Peak1 / 21
    (9)Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • DVD Player
    • Washer
    • Balcony
    • Wi-Fi
    • Parking
    • Outdoor Dining Area
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Hinsdale, Berkshires 01235
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshire Blueberry Lodge LLC - Near Jiminy Peak1 / 24
    (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
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    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...
    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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    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,...
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    Stephentown, New York 12168
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Wyndham Bentley Brook - Fri-Fri, Sat-Sat, Sun-Sun only!1 / 8
    (1)Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2017
    Two couples with similar music, arts, culinary, hiking, shopping and just chillin' tastes would definitely reserve the two bedroom/two bath deluxe unit any Wyndham Bentley...
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. 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...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Shared Indoor Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lodging at the highest rated resort at Jiminy Peak Mountain--Wyndham Bently Brook Resort-Mountainside What is Jiminy Peak Known For---The Best Skiing in the Berkshire Mountains tucked away in Hancock, Ma. 2 Bedroom Unit consisting of-King bed master, 2 doubles 2nd bedroom and a queen sleep...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Berkshires Vacation Rental - Bentley Brook Resort Suite1 / 16
    (2)Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    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...
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    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...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshire Mountain Lodge - Fri, Sat,Sun check ins only!  Inbox x1 / 5
    (3)Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2017
    We traded in from RCI and had a great stay! The staff and grounds were fantastic. I trade all over the US, and this place is quiet and clean. Boston is only a couple hours...
    Reviewed 18 June 2017
    We Loved the Berkshire Mountain Lodge. Just got back yesterday. We stayed for seven nights. It is quiet as all the rooms consist of one bedroom, living room, large bathroom and...
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Located near Lenox, Massachusetts and among the picturesque Berkshire highlands lies the Berkshire Mountain Lodge. Ideal no matter the season, Berkshire Mountain Lodge offers a...
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    Pittsfield, Berkshires 01201
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Golden Triangle in the Berkshires1 / 4
    (1)Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 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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    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...
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    Hancock, Berkshires 01237
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please email or call to confirm availability. Ski-In/Ski-Out Resort! Wyndham Bentley Brook is located right at the base of Jiminy Peak ski mountain, with ski lifts only 200 feet from the resort's front door. In winter, you can ski right out the door to the lifts. In spring, summer and fall,...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy great year round activities from white water rafting and hiking in the summer, to skiing at the famous Jiminy Peak at this ski in ski out resort. The newly opened Ramblewild Aerial Park is the talk of the town! Your 2 bedroom private condo sleeps 8. It has a king size bed in the master...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    PanoramicView1000 sq ft Guest Quarters Berkshires1 / 16
    (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
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to aview of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
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    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...
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    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have this in both 1 and 2Br, so please confirm which you want. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for a...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation Village in the Berkshires accommodations feature spacious floor plans for maximum comfort. Kitchen, living and dining room in each suite are integrated for entertaining and enjoyment. Designated suites meet Americans with Disabilities Act (ADA) requirements. Unit Features Individual...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The vacation house at Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak and to many cultural attractions of the Berkshires, 'America's Premier Cultural Resort', including Williamstown Theater Festival, the Clark Art Museum, Hancock Shaker Village and Tanglewood. For...
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    Hancock, Berkshires 01237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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
    Kid friendly
    Smoking allowed
    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...
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    Kid friendly
    Smoking allowed
    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...
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    Pittsfield, Berkshires 01201
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 18
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The...
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    Hancock, Berkshires 01267
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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