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Hancock Holiday Rentals

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    Travellers to Hancock are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    Wyndham Bentley Brook at Jiminy Peak1 / 21
    (9)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • 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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    Wyndham Bentley Brook1 / 19
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    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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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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 - Fri-Fri, Sat-Sat, Sun-Sun only!1 / 8
    (1)Excellent
    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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    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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    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Golden Triangle in the Berkshires1 / 4
    (1)Very good
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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
    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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    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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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2200sf Country House on 16 Acres-2 Miles to Jiminy1 / 14
    (3)Very good
    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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    Hancock, Berkshires 001237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Satellite TV
    • Shared Indoor Pool
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    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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    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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    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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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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. 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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    Jiminy Peak 4 LEVEL LUXURY ALL YEAR ROUND CONDO ALSO WINTER SKI RENTAL1 / 24
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Hot Tub
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    • Sauna
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Hancock, Berkshires 01237
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Artsy Jiminy Peak Rental1 / 24
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
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    • Internet Access
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    Pet friendly
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Walk To Slopes From This Fantasitc Condo1 / 11
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    Luxury Mountainside Ski In/Ski Out - Jiminy Peak Resort in the Berkshires1 / 24
    (55)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    New Huge Beautiful House-16 Acres-2 miles from Jiminy! Summer available1 / 22
    (4)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Hancock, Berkshires 01237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Create Lasting Family Memories in Massachusetts1 / 24
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Updated Mountainside Condo, Easy Acces on Mountain 50% OFF FOR JULY TO SEPT1 / 21
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Satellite TV
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    • Internet Access
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    Pet friendly
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    Smoking allowed
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    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Hancock, Berkshires 01267
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ski In/Ski Out - Premium Jiminy Peak Mountain Resort- Berkshires1 / 24
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Washer
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Rates! BEAUTIFUL Ski-In/Ski-Out - Jiminy Peak Mountain Resort - Berkshires1 / 24
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
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    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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