Find Ski Hotels in The Berkshires, MA
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Sep 11 - Sep 12Tomorrow
Sep 12 - Sep 13This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Our 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.
￥17,909
￥20,004 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.
￥12,227
￥17,090 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.
￥19,293
￥21,550 total
includes taxes & fees
Sep 22 - Sep 23
4. The Red Lion Inn
The Red Lion InnStockbridge
- Step into winter wonderland at this historic hotel, where skiing adventures and mountain relaxation unite just steps from scenic trails.
￥24,243
￥34,710 total
includes taxes & fees
Sep 23 - Sep 24
￥22,178
￥24,774 total
includes taxes & fees
Sep 13 - Sep 14
6. 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.
￥20,584
￥22,993 total
includes taxes & fees
Sep 20 - Sep 21
￥20,727
￥23,153 total
includes taxes & fees
Sep 13 - Sep 14
8. 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.
￥17,972
￥23,079 total
includes taxes & fees
Sep 16 - Sep 17
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4-star ski hotels in The Berkshires
￥63,146
￥70,534 total
includes taxes & fees
Sep 13 - Sep 14
￥15,180
￥16,955 total
includes taxes & fees
Oct 4 - Oct 5
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
￥50,717
￥61,353 total
includes taxes & fees
Sep 28 - Sep 29
￥50,691
￥61,169 total
includes taxes & fees
Oct 8 - Oct 9
￥36,513
￥40,785 total
includes taxes & fees
Sep 17 - Sep 18
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
The Yankee Inn
10/10 Excellent
"Nasically a large motel with both an outdoor and indoor pool. A bit tired, but reasonably close to Lenox and to Tabglewood."
The Cornell Inn, Lenox & The Berkshires
10/10 Excellent
"Great and helpful staff. Delicious complimentary drinks and a free bottle of wine in your room!!"
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Great location for Mass Moca"
Best Western Plus Berkshire Hills Inn & Suites
8/10 Good
"Clean, staff was great, and ample parking"
Willows Motel Williamstown
10/10 Excellent
"Awesome staff plus pet-friendly."
Jiminy Peak Mountain Resort
10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
Hotel On North
10/10 Excellent
"Best place in town"
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