Find Ski Hotels in Pittsfield, MA
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Oct 2 - Oct 4Our top choices for Pittsfield ski hotels
1. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
- Ski the Berkshires from a central Pittsfield hotel with an indoor pool, just minutes from multiple slopes and trails for winter fun.
NT$3,469
NT$3,875 total
includes taxes & fees
Oct 19 - Oct 20
NT$4,487
NT$5,012 total
includes taxes & fees
Oct 18 - Oct 19
3. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
NT$2,533
NT$3,540 total
includes taxes & fees
Oct 1 - Oct 2
4. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
- Nestled near premier ski areas, this cozy retreat offers mountain adventures and a fitness center for year-round active stays.
NT$3,366
NT$3,760 total
includes taxes & fees
Oct 18 - Oct 19
NT$3,120
NT$3,485 total
includes taxes & fees
Oct 8 - Oct 9
NT$4,655
NT$5,200 total
includes taxes & fees
Sep 27 - Sep 28
7. Berkshire Inn
Berkshire InnPittsfield
- Snow-covered paradise beckons with ski adventures and a seasonal outdoor pool, all conveniently located in the heart of Pittsfield.
NT$2,737
NT$3,057 total
includes taxes & fees
Sep 21 - Sep 22
8. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
- Warm up on the slopes at Bousquet Ski Area, just minutes away from this cozy Pittsfield retreat with an indoor pool and hot tub.
NT$3,628
NT$4,052 total
includes taxes & fees
Oct 19 - Oct 20
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Top Pittsfield Hotel Reviews
The Yankee Inn
10/10 Excellent
"The staff ,as always, were excellent. George, Carl, and Shelley are always a pleasure to deal with. We love your weekend bar."
Vacation Village in the Berkshires
10/10 Excellent
"Love this place for a weekend getaway."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
The Red Lion Inn
8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Nice place, would stay again"
Hilton Garden Inn Lenox Pittsfield
8/10 Good
"Hotel was very clean, spacious, and staff was very courteous. Bar and restaurant onsite are hood, Guidos market is right in front and is AMAZING!! Definitely a great value and comfortable!"
The Central Downtown Inn & Suites
8/10 Good
"It was priced well. The central location was convenient. The space inside was much larger than usual. There was a bedroom, living room and dining room combo with a full kitchen. It appears that it was an apartment at one time."
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- Frelinghuysen Morris House and Studio
- Visit Middlefield
- Visit West Stockbridge
- Lee Premium Outlets
- Norman Rockwell Museum
- Visit Housatonic
- Canoe Meadows Wildlife Sanctuary
- Visit South Lee
- Visit Lee
- Mount Greylock State Reservation Visitor Center
- Bousquet Ski Area
- Pleasant Valley Wilderness Sanctuary
- Kushi Institute
- National Shrine of the Divine Mercy
- Greenock Country Club
- South Lee Vacations
- Charles H. Baldwin & Sons
- Williamstown Theatre Festival
- Visit Hancock
- Visit Lanesborough
- Mission House
- Crane Museum of Papermaking
- Visit Dalton
- Animagic Museum of Animation
- Berkshire Botanical Garden
- Lenox Mountain
- Visit Lenox