Find Ski Hotels in The Berkshires, MA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Ski Hotels
Tonight
Sep 19 - Sep 20Tomorrow
Sep 20 - Sep 21Next weekend
Sep 25 - Sep 27In two weeks
Oct 2 - Oct 4Our top choices for The Berkshires ski hotels
1. The Yankee Inn
The Yankee InnLenox
- Embrace winter magic at this mountainside retreat offering an indoor pool, hot tub, and direct access to Bousquet Ski Area.
₩160,225
₩178,971 total
includes taxes & fees
Sep 22 - Sep 23
2. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
₩109,947
₩153,667 total
includes taxes & fees
Oct 1 - Oct 2
3. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
- Winter wonderland awaits at lakefront ski haven; fuel adventures with free breakfast and relax by panoramic waters.
₩176,248
₩196,869 total
includes taxes & fees
Sep 29 - Sep 30
₩195,835
₩218,747 total
includes taxes & fees
Oct 18 - Oct 19
5. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
- Winter adventures await at riverside Holiday Inn Express in Great Barrington, steps away from premier ski slopes and hiking trails.
₩171,275
₩191,313 total
includes taxes & fees
Oct 19 - Oct 20
6. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
- Alpine ski resort getaway awaits with 4 pools, mini-golf, and endless winter adventures in the beautiful Berkshires.
₩161,606
₩207,518 total
includes taxes & fees
Sep 21 - Sep 22
7. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
- Explore ski paradise at Jiminy Peak with mountainside hot tubs and slope-view relaxation at this Williamstown family retreat.
₩132,145
₩162,842 total
includes taxes & fees
Sep 21 - Sep 22
₩191,413
₩213,809 total
includes taxes & fees
Sep 20 - Sep 21
View all properties
4-star ski hotels in The Berkshires
₩136,154
₩152,085 total
includes taxes & fees
Oct 8 - Oct 9
₩304,030
₩339,600 total
includes taxes & fees
Sep 21 - Sep 22
₩455,813
₩550,028 total
includes taxes & fees
Sep 20 - Sep 21
₩606,369
₩677,310 total
includes taxes & fees
Oct 1 - Oct 2
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodStockbridge
₩717,325
₩867,765 total
includes taxes & fees
Oct 12 - Oct 13
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all propertiesTop The Berkshires Hotel Reviews
Vacation Village in the Berkshires
8/10 Good
"Very quiet property."
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."
Best Western Plus Berkshire Hills Inn & Suites
8/10 Good
"Clean, staff was great, and ample parking"