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Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA

Photo gallery for Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA

Summer exterior of house/front porch
Black Diamond Mountainside Drive entrance
Winter exterior photo of house and mountain view of Jiminy Peak
Winter exterior of house/front porch
Main floor living room

Reviews

10 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 10241.5 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Hancock, MA
  • Place, Jiminy Peak Mountain Resort
    ‪2 min walk‬
  • Place, Mountain Coaster
    ‪7 min walk‬
  • Place, Alpine Super Slide
    ‪16 min walk‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪27 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Children's Blue Bunk Room

1 Double Bed and 1 Single Bed

Children's Green Room

1 Double Bed

Children's Red Bunk Room

1 Single Bunk Bed

Main Floor Bedroom

1 Queen Bed

Master Bedroom

1 King Bed and 1 Double Sofa Bed

3 bathrooms

Lower Level Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Main Floor Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Master Bathroom

Soap · Towels provided · Toilet · Jetted bathtub · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

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.

5 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

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 12:00 PM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

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

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
Property Registration Number C2105284400

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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Hancock, MA

What's nearby

  • Jiminy Peak Mountain Resort - 2 min walk - 0.2 km
  • Mountain Coaster - 7 min walk - 0.6 km
  • Alpine Super Slide - 16 min walk - 1.4 km
  • Tanglewood Music Center - 39 min drive - 58.1 km
  • Colonie Center Mall - 46 min drive - 63.9 km

Getting around

  • Pittsfield Intermodal Transportation Center - 23 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 29 min drive

Restaurants

  • ‪Dunkin' - ‬17 min drive
  • ‪Cumberland Farms - ‬10 min drive
  • ‪Old Man Jeff’s Barbecue Company - ‬22 min drive
  • ‪Bob's Country Kitchen - ‬14 min drive
  • ‪Proprietor’s Lodge - ‬20 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 27 Mar 2026, prices found for a 1-night stay for 2 adults at Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA on 1 Apr 2026 start from AU$914, 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

África M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for families

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.
Stayed 45 nights in Jun 2025
Verified

10/10 Excellent

Stuart L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Jiminy Peak Family visit

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.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Anna S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great rental at Jiminy Peak

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.
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Emily W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nothing short of perfect!

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!
Stayed 3 nights in Oct 2023

About the host

Hosted by Jill

Host profile image
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.
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