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Lanesboro Vacation Rentals

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    Don't let other travellers get your favourite Lanesboro area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 30 Rentals in Lanesboro
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    Stone School Cottage1 / 10
    (15)Very good
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Lanesboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 10 kilometres of Lanesboro.
    Berkshire's Getaway ---Peace & Tranquility1 / 20
    (3)Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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 3 weeks ago
    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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    PanoramicView1000 sq ft Guest Quarters Berkshires1 / 16
    (2)Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    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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    Wyndham Bentley Brook at Jiminy Peak1 / 21
    (9)Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 26 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...
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    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...
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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
    • Air Conditioning
    • Satellite TV
    • Private Indoor Pool
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Sauna
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • 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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    Cheshire
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study,...
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    Cheshire, Berkshires 01225
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Wyndham Bentley Brook1 / 19
    (3)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
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We had our family reunion there in July. Everything was set up very well for our group. There were activities for the younger kids, tennis courts were in fine shape and pools...
    Reviewed 27 June 2017
    Had a great experience booking with Christian at the Wyndham Bentley - Everything was clean tidy and new - very much enjoyed and hope to be coming back
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    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...
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    Location Information
    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
    • Sauna
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Booking stays under 3 days may be possible. Please inquire for more information Bentley Brook is a colorful resort located in Hancock, Massachusetts. This spacious hotel also has the majestic Bershire Mountains, which is apart of the Appalachians, at it’s front door. This resort offers scenic...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps from the main lifts this 3 Bedroom unit can accommodate up to 8 guests; with all the comforts of home. Master bedroom, with Queen-size bed, wall mounted TV, large closet and a view of the Cricket lift and learning slope. The master bath has duel sinks, jet tub, body sprays and washer and...
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    • Balcony
    • Shared Indoor Pool
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our home on Jiminy Peak! This beautiful, luxury unit was just renovated for the 2016 ski season. It is fully equipped with everything a family will need for the perfect Mountainside vacation. Two Bedrooms accommodates 6+ guests with all the comforts of home. 10 foot ceilings and crown...
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    Dalton
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Dalton, Berkshires 01226
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    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
    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
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Wi-Fi
    • Terrace
    • DVD Player
    • Washer
    • Central Heating
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Hancock, Berkshires 01237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2200sf Country House on 16 Acres-2 Miles to Jiminy1 / 14
    (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
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hancock, Berkshires 001237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    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
    Kid friendly
    Smoking allowed
    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...
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    Hancock, Berkshires 01267
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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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
    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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    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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    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
    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Booking stays under 3 days may be possible. Please inquire for more information Bentley Brook is a colorful resort located in Hancock, Massachusetts. This spacious hotel also has the majestic Bershire Mountains, which is apart of the Appalachians, at it’s front door. This resort...
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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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.
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! Nestled along the scenic border of New York and Massachusetts in the beautiful Berkshire Mountains, this pristine Hancock vacation rental condo comfortably accommodates 6...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hancock
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Booking stays under 3 days may be possible. Please inquire for more information Bentley Brook is a colorful resort located in Hancock, Massachusetts. This spacious hotel also has the majestic Bershire Mountains, which is apart of the Appalachians, at it’s front door. This resort...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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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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    Location Information
    Hancock, Berkshires 01267
    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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    • 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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    Location Information
    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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    • 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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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Private Berkshire Home on 27 acres near Jiminy Peak1 / 25
    (11)Excellent
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Outdoor Dining Area
    • Washer
    • Central Heating
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2016
    Just got back from our stay at the Wolfs Den and i already cant wait to go back! Its a great place for a friends trip or a family trip! Nestled in the woods with a beautiful...
    Reviewed 23 August 2016
    Thanks Kevin for renting your place to us. We love it there!!! The place is nice and cozy for our family. Everything we needed was all there. My family have a great time there...
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    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...
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    Location Information
    Hancock, Berkshires 01237
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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