Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA
Welcome to Jiminy Peak Mountain Resort in the Berkshire Mountains! Our newly-renovated mountain retreat "The Lazy Bear" is one of only a handful of FREE-STANDING HOUSES in the exclusive Black Diamond section of Jiminy Peak. The Lazy Bear boasts a quiet location on a dead-end street and 3 levels of luxury living complete with a spacious master suite, oversized great room with a wood-burning fireplace, a large tv/game room, and spacious outdoor deck with a gas grill and 360-degree mountains views. *Sleeps up to 4 adults & 6 children, no exceptions. Events and parties and strictly prohibited. House is priced accordingly.
4 Bed/3 Bath Newly renovated, free-standing Exclusive Black Diamond, Mountainside, Jiminy Peak Ski-in/ski-out, Private owner's entrance to the slopes directly onto Grouse Run 360-Degree Mountain Views in Winter Months 2600+sf & 3 Levels of Living Spacious, light-filled Great Room with Wood Burning Indoor Fireplace Large, accommodating Dining Area Chef's Kitchen w/brand new appliances and luxury cookware Luxurious wood Lower Level Living/Game Room w/Foosball Separate Ski Room Entrance/Wet Room w/Dryers Gas Cooking, Indoor & Out Luxurious Wool Carpeting in Bedrooms Large Laundry Room with Washer/Dryer Large Balcony w/ Slope Views and Gas Grill Oversized, private Master Bedroom Private, dead-end, neighbors on only one side Alarm System & Nest Doorbell Wi-Fi Two Smart Televisions Year-round access to the pool at The Country Inn Summer access to tennis courts Smoke & pet-free
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Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
The host requires you to complete the following before checking out:
Load and start the dishwasher
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
Due to owner's severe allergies, we cannot accommodate pets, therapy or service animals.
Identification matching the reservation must be provided prior to check-in as well as a list of all guests that will be in the house.
Important information
You need to know
Property Registration Number C2105284400
Property # 3316105vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Hancock
Located in Hancock, this holiday home is in the mountains. Mountain Coaster and Alpine Super Slide are local attractions and those in the mood for shopping can visit Guido's Marketplace and Colonial Plaza. Travelling with kids? Consider Zema's Nursery and Lichtenstein Center for the Arts. Discover the area's water adventures with nearby swimming, or enjoy the great outdoors with horse riding, mountain biking and cycling.
Pittsfield Intermodal Transportation Center - 23 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 29 min drive
Restaurants
Cumberland Farms - 10 min drive
JJ's Lodge - 16 min walk
Old Man Jeff’s Barbecue Company - 22 min drive
Dunkin' - 17 min drive
Bob's Country Kitchen - 14 min drive
Frequently asked questions
Does Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA?
As of 11 May 2026, prices found for a 1-night stay for 2 adults at Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA on 12 May 2026 start from NZ$1,056, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA pet-friendly?
No, pets are not allowed at this property.
How much is parking at Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA?
On-site parking is available at the property.
What time is check-in at Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA?
Check-in begins at 4:00 PM.
What time is check-out at Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA?
Checkout is at 12:00 PM.
Where is Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA located?
Located in the mountains, this Hancock holiday home offers ski-in/ski-out access within 3 miles (5 km) of Jiminy Peak Mountain Resort, Alpine Super Slide and Mountain Coaster. Mount Greylock State Reservation and Taconic Ridge State Forest are also within 6 miles (10 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We stayed in Jill's house for just over a month. It was perfectly comfortable, lovely relaxed scenery and just a short drive away from everything you might need. Jill was a very responsive host and fixed a couple issues we had super efficiently.
The house is at the end of the street towards the top of the hill and is very quiet. It is very well equipped with everything that you could need. The host responded to any questions very quickly. We had a rainy week but still found lots to do in the area and at the mountain. I would highly recommend this property to anyone.
What a great house! We were 2 families with 6 children and the house suited us perfectly. It had a great basement where the children watched tv and played with all the games provided. The house was extremely well stocked and well furnished. The host was very responsive and dealt with any issues we had very quickly. Would highly recommend.
We just returned from a magical weekend in Hancock. Our hotel cancelled on us last minute and this host went way above and beyond to be accommodating and supportive so we could still enjoy our vacation! The home is immaculate - we’ve stayed at many, many rental homes and this was among the nicest for sure. Spacious, bright, everything perfectly decorated and comfortable! Lovely private mountain setting. Awesome downstairs space with playroom
And bedrooms for the kids. We loved it!
Emily W.
Stayed 3 nights in Oct 2023
About the host
Hosted by Jill
Mom of 3 boys from Long Island, New York.
Why they chose this property
We fell in love with Jiminy Peak because it's a small, friendly mountain our children can navigate on their own and grow as skiers. It's location is in the heart of the Berskshire Mountains with easy access to Great Barrington, Stockbridge, Lee, Lenox, Pittsfield, Adams and Williamstown.
What makes this property unique
We updated the Lazy Bear so it feels fresh, clean and new. What sets this house apart, besides the beautiful, upscale décor, is the home's layout. It's 3 floors of living with 2 living rooms. The children have their own space on the ground floor. The house is free-standing, very private, and surrounded by mountains. We love that it's in the heart of the Berkshires and everything the area offers.