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Holiday Homes and Apartments Cheshire, MA and nearby

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    Cheshire
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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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 / 20
    5 of 5 stars (2) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Mountain Views
    • Patio
    • Grill
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! This excellent property carries an abundance of amenities to make your northeast vacation one you’ll always cherish. Nestled along the scenic border of New York and... View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 24
    5 of 5 stars (5) Excellent
    Stephentown, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • 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 12168
    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...
    5 of 5 stars Reviewed 21 November 2015
    I attended a group weekend workshop at the Berkshire Blueberry Lodge in Stephentown; foothills of the Berkshires. I cannot tell you how beautiful the lodge is; the breathtaking...
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    1 / 10
    5 of 5 stars (14) Excellent
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Internet Access
    • DVD Player
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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. We are about 8 minutes away from Jiminy Peak and... View all property information
    Location Information
    Lanesboro, Berkshires 01237
    5 of 5 stars Reviewed 13 February 2016
    My boyfriend and I celebrated my birthday weekend at the cottage. We had a rough start the day we were to arrive and Cheryl was just wonderful and so understanding. We were...
    5 of 5 stars Reviewed 6 October 2015
    My husband and I just returned from a fabulous weekend getaway in the Berkshires. We chose the Stone School Cottage but it's privacy, central location, and unique character. We...
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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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    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Hancock, Berkshires 01237
    4 of 5 stars 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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    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 01237
    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 / 16
    4.5 of 5 stars (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
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed 6 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...
    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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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Private Indoor Pool
    • Sauna
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Discover an unparalleled vacation destination at Wyndham Bentley Brook. This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal activities, return to your... View all property information
    Location Information
    Hancock, Berkshires 01237
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    1 / 6
    5 of 5 stars (3) Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Savoy, Berkshires 01256
    5 of 5 stars Reviewed 4 February 2016
    What a quaint and absolutely lovely place to have spent the weekend. The quiet and peaceful surroundings along with the gorgeous wood interior made for a very homey and...
    5 of 5 stars Reviewed 9 December 2015
    Words can't begin to describe how amazing this rental is! My husband and I were married in November of 2014. Being a teacher, we couldn't go away for a long honeymoon so we...
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    1 / 19
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 10 September 2015
    The units are clean and spacious and well stocked. Movie theater, swimming pools, outdoor picnic area with grills. and the mountain adjacent has plenty of outdoor activities...
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    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Mountain Views
    • Grill
    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Hancock, Berkshires 001237
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Terrace
    • Central Heating
    • DVD Player
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak (less than 5 minutes away) and to many cultural attractions of the Berkshires including Williamstown Theater Festival and Tanglewood. For outdoor lovers, Whitman Woods is near Mount Greylock Reservation, Audubon's... View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 8
    4 of 5 stars (2) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    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...
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    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Outdoor Dining Area
    • Parking
    • Shared Garden
    • Central Heating
    • DVD Player
    • Washer
    • Internet Access
    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 01235
    Lanesboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Patio
    • Central Heating
    • DVD Player
    • Mountain Views
    • Washer
    • Hot Tub
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and all the furnishings are new... View all property information
    Location Information
    Lanesboro, Berkshires 01224
    Stephentown, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Two story cape that can sleep up to 12 people on 50 acres. Fully equipped kitchen, laundry area and dining & living room that faces the Berkshire Mountains. Relaxingy deck with barbecue. Walking trails and swimming pond make it a perfect getaway place. Wifi, a/c tv Near all Berkshire attractions,... View all property information
    Location Information
    Stephentown, New York 12168
    1 / 25
    5 of 5 stars (9) Excellent
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Outdoor Dining Area
    • Washer
    • Central Heating
    • Grill
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 5 weeks ago
    This was a perfect weekend retreat for our extended family of six (three adult couples). The house is very warm and inviting, clean, and well-equipped. The surrounding woods and...
    5 of 5 stars Reviewed 8 July 2015
    My eight year old daughter and I had a wonderful time staying in Hancock. We were joined at different times by young cousins and grandparents - the kids loved the inside (the bunk...
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    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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 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...
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    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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 01237
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Hancock, Berkshires 01237
    Stephentown, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Parking
    • Washer
    • Mountain Views
    • Private Garden
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Perfect weekend retreat or short term furnished rental close to all Berkshire, MA amenities and Jiminy Peak Mountain Resort, museums, theatre, restaurants, shopping and more! 20 Minutes to Williamstown, 25 to Pittsfield, 30 to Albany. Home is efficient, easily maintained in an adorable 1870's... View all property information
    Location Information
    Stephentown, New York 12168
    Pittsfield
    7 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    • 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 01201
    1 / 47
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Washer
    • Balcony
    • DVD Player
    • Terrace
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to our home! This beautiful, luxury unit is fully equipped with everything a family will need for the perfect Mountainside vacation. 3 Bedrooms accommodates 8 guests with all the comforts of home. Master bedroom, with Queen-size bed, wall mounted TV, large closet and a view of the... View all property information
    Location Information
    Pittsfield, Berkshires
    1 / 16
    4 of 5 stars (2) Very good
    Stephentown, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
    • Parking
    • Satellite TV
    • Balcony
    • DVD Player
    • Internet Access
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful three bed room home with a private master bedroom with attached bath and deck. Two bedrooms downstairs with a shared bathroom. Modern Kitchen with everything you need to make wonderful meals, Large deck out the back with tables, chairs and gas grill. House has a spacious living room with... View all property information
    Location Information
    Stephentown, New York 12169
    4 of 5 stars Reviewed 29 October 2014
    Beautiful home, comfortable BUT there were no sheets on the bed. And when I contacted the owner nothing was done about it. Kitchen was outfitted with everything. There was a...
    4 of 5 stars Reviewed 28 July 2014
    We had a great time and would recommend this house to anyone looking for a quiet escape. The house was in great condition, with full kitchen, lots of room, carpeting, amazing...
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    ***PRICE AND AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. PLEASE INQUIRE ABOUT DATES AND PRICE PRIOR TO SUBMITTING PAYMENT*** 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... View all property information
    Location Information
    Hancock, Berkshires 01237
    Dalton
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • DVD Player
    • Patio
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This home is an exact replica of the first Colonial ever built in Massachusetts back in the 1600's. It is called the "Parson Capens Home" and is located in Topsfield Mass. It has the design of the old but all the modern features. The home is nestled in the mountains of Berkshire County which have... View all property information
    Location Information
    Dalton, Berkshires 01226
    Hancock
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Sauna
    • Patio
    • Balcony
    • Mountain Views
    • Hot Tub
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pool. Go hiking, biking, fishing or horseback riding around the property or enjoy the off site... View all property information
    Location Information
    Hancock, Berkshires 01267
    Stephentown, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
    • Balcony
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Washer
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This cozy cottage is perfect for a small group of friends or a family getaway in the beautiful Berkshires. We're on 120 acres of private woods but only 7 miles from Jiminy Peak. The main space features a cathedral ceiling in the open living/dining area, with a glass-front woodstove for chilly... View all property information
    Location Information
    Stephentown, New York 12168