Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
31 min drive
Rooms & beds
4 bedrooms (sleeps 12)
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Kitchen
Balcony
Garden
About this property
Comfortable Berkshires retreat on mtn resort, SISO
Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a chalet: perfect after a ski/hike/bike through the beautiful mountains around it. 4 bdrs allow your group to space out, and a great room with 20 foot high ceilings extends through the dining area. Convenient to many Berkshires spots (Tanglewood, museums, etc.), a 2nd living room, fireplace, jacuzzi, and access to slopes, hot tubs, heated pool & gym complete the perfect getaway.
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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
About the area
Hancock
Hancock is home to this holiday home. Mount Lebanon Shaker Village and Colonial Theater are local landmarks, and travellers looking to shop may want to visit Guido's Marketplace and Colonial Plaza. Mountain Coaster and Alpine Super Slide are also worth visiting.
Pittsfield Intermodal Transportation Center - 28 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 30 min drive
Restaurants
Cumberland Farms - 10 min drive
JJ's Lodge - 16 min walk
Old Man Jeff’s Barbecue Company - 23 min drive
Dunkin' - 17 min drive
Bob's Country Kitchen - 14 min drive
Frequently asked questions
Does Comfortable Berkshires retreat on mtn resort, SISO have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Comfortable Berkshires retreat on mtn resort, SISO?
As of 8 May, 2026, prices found for a 1-night stay for 2 adults at Comfortable Berkshires retreat on mtn resort, SISO on 21 Aug, 2026 start from S$581, 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 Comfortable Berkshires retreat on mtn resort, SISO pet-friendly?
No, pets are not allowed at this property.
How much is parking at Comfortable Berkshires retreat on mtn resort, SISO?
On-site parking is available at the property.
What time is check-in at Comfortable Berkshires retreat on mtn resort, SISO?
Check-in begins at 4:00 PM.
What time is check-out at Comfortable Berkshires retreat on mtn resort, SISO?
Checkout is at 11:00 AM.
Where is Comfortable Berkshires retreat on mtn resort, SISO located?
Situated in Hancock, this holiday home is 0.6 mi (0.9 km) from Jiminy Peak Mountain Resort and within 3 miles (5 km) of Alpine Super Slide and Mountain Coaster. Mount Greylock State Reservation and Taconic Ridge State Forest are also within 9 miles (15 km).
Reviews
8.4
Very good
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The location was excellent, within walking distance of ski trail. Wonderful view of the ski area and surrounding mountains. The fireplace was perfect for the end of the day. Our large family had plenty of space to have fun together or chill alone. We had concerns about the cleanliness and working conditions of some electronics. Our concerns were communicated with the owner, and the response was positive. I am sure with corrections this Comfortable Berkshire Retreat will be a 5 star stay.
Russell R.
Stayed 3 nights in Mar 2026
Verified
10/10 Excellent
Javier
25 Jul, 2025
Liked: Cleanliness, amenities, property conditions & facilities, communication
We had a great stay at Carl's townhouse. He was super helpful and great to work with. He took the time to arrange for us to check in earlier than advertised. The kitchen was well stocked, and the house was clean. There was plenty of room and it was very comfortable. Hope to visit again soon!
Alyson A.
Stayed 1 night in Mar 2025
Verified
4/10 Poor
Rowena
28 Jul, 2025
Disliked: Cleanliness, property conditions & facilities, communication
Jiminy Peak has passed its prime and is "tired" looking. My family experienced one disappointment after another with our lodging. My sister had to vacate the premises because everytime she was present her sensitivity to mold/mildew kicked in and she felt sick. She and 5 other family members had to find new lodging. The HVAC was leaking and the carpet wet in the basement. A technician did not arrive until day 6 of our 7 day vacation. The front door key pad was broken and we could not lock our possessions securely. One of the beds was broken and maintenance never addressed the issue though notified on day 1. I had to sleep on a mattress on the floor. One bed was very hard and very squeaky. The master bedroom mattress was lopsided and my 89 year old mother had to sleep across it at an angle to keep from rolling off. The master bathroom door would not close. There was no hand railing to help my elderly mother get in the tub. There was a pet odor in the entry hall. Multiple lights did not work and the shower was dark in one bathroom. The living room furniture is worn and the carpets are outdated. The deck needed powerwashing and there were no table and chairs to eat outside. One of two lounge chairs was rotting. The sliding screen door to the deck had holes in it and would not slide or fit properly in the runners. One of the kitchen outlets did not work. No instructions for trash disposal. Pool is not next to the home as shown in the photos. Kitchen equipped fine.
Rowena
Stayed 7 nights in Jul 2025
Verified
4/10 Poor
Chris G.
22 Apr, 2026
Disliked: Cleanliness, communication
Chris G.
Stayed 5 nights in Jan 2026
Verified
10/10 Excellent
Meghan C.
26 Oct, 2025
Meghan C.
Stayed 2 nights in Oct 2025
About the host
Your host
Premier Host
They consistently provide great experiences for their guests