Find Ski Hotels in The Berkshires, MA
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25 Sep - 27 SepOur 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.
AED 426
AED 476 total
includes taxes & fees
22 Sep - 23 Sep
2. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Alpine retreat with ski adventures awaits at Berkshire Mountain Lodge in the snow-capped mountains.
AED 292
AED 409 total
includes taxes & fees
1 Oct - 2 Oct
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.
AED 459
AED 513 total
includes taxes & fees
21 Sep - 22 Sep
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.
AED 592
AED 843 total
includes taxes & fees
23 Sep - 24 Sep
AED 528
AED 589 total
includes taxes & fees
14 Sep - 15 Sep
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.
AED 474
AED 529 total
includes taxes & fees
20 Sep - 21 Sep
AED 493
AED 551 total
includes taxes & fees
14 Sep - 15 Sep
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.
AED 430
AED 552 total
includes taxes & fees
15 Sep - 16 Sep
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4-star ski hotels in The Berkshires
AED 360
AED 402 total
includes taxes & fees
5 Oct - 6 Oct
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
AED 1,213
AED 1,467 total
includes taxes & fees
28 Sep - 29 Sep
AED 1,212
AED 1,463 total
includes taxes & fees
15 Sep - 16 Sep
AED 1,502
AED 1,678 total
includes taxes & fees
15 Sep - 16 Sep
AED 804
AED 898 total
includes taxes & fees
21 Sep - 22 Sep
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
"Loved the pond trail! What a nice shift after a long day on the road."
Quality Inn Great Barrington
10/10 Excellent
"The rooms looked to be newly renovated, very clean and the staff was friendly and helpful. Walkable to town and restaurants."
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Best Western Plus Berkshire Hills Inn & Suites
8/10 Good
"Clean, staff was great, and ample parking"
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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