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Top Hillsdale Ski Hotels

The Brooks Motel

2.0 star property
Hillsdale
  • Ski lifts nearby
  • Snowboarding nearby
7.4 out of 10, Good, (115)
The Brooks Motel

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Ski lifts nearby
  • Snowboarding nearby
  • Ski passes
  • Ski equipment rentals nearby
8.6 out of 10, Excellent, (1026)
Mountain enthusiasts thrive at this ski-friendly hotel with easy access to Bousquet Ski Area and Jiminy Peak Mountain Resort. Spacious rooms provide comfort after exhilarating days of skiing, snowboarding, or cross-country adventures, while complimentary breakfast fuels tomorrow's slopes.
The price is ฿3,028
฿3,383 total
includes taxes & fees
10 Nov - 11 Nov
Best Western Plus Berkshire Hills Inn & Suites

Monument Mountain Motel

2.5 star property
Great Barrington
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • Microwave
  • Extra beds/cots
9.0 out of 10, Wonderful, (782)
Powder enthusiasts flock to this spotless mountain motel for its prime location near Ski Butternut, just 3 miles away. Comfortable rooms feature refrigerators and microwaves perfect for après-ski snacks. Barbecue grills and picnic areas welcome outdoor gatherings after thrilling downhill adventures.
Monument Mountain Motel

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Ski lifts nearby
  • Snowboarding nearby
  • Ski passes
8.0 out of 10, Very good, (941)
Mountain adventures begin at this ski-friendly hotel where cross-country trails and downhill slopes await nearby. After exhilarating snow activities, guests revitalise in the heated indoor pool and health club. The on-site restaurant serves delicious meals perfect for refuelling between winter excursions.
The price is ฿3,175
฿3,546 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Snowboarding nearby
  • Ski passes
  • Hot tub
9.2 out of 10, Wonderful, (1000)
Powdery slopes beckon just moments away from this ski-friendly haven where winter adventures begin. After exhilarating runs, soothe tired muscles in the indoor pool or hot tub while enjoying spectacular mountain panoramas. Mornings start with complimentary made-to-order breakfast before another day conquering nearby trails.
The price is ฿3,287
฿3,671 total
includes taxes & fees
18 Nov - 19 Nov
The Yankee, Trademark Collection by Wyndham

Shaker Mill Inn

2.5 star property
West Stockbridge
  • Breakfast included
  • Parking included
  • Free WiFi
  • Housekeeping
9.6 out of 10, Exceptional, (433)
Mountain escapades flourish at this charming inn, where skiing enthusiasts find pristine trails just steps away. Nestled in West Stockbridge, active travellers enjoy cross-country and downhill skiing before returning to peaceful accommodation. Complimentary breakfast fuels outdoor adventures in this serene county setting.
The price is ฿3,531
฿3,874 total
includes taxes & fees
12 Nov - 13 Nov
Shaker Mill Inn

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
  • Snowboarding nearby
  • Skiing lessons nearby
  • Ski equipment rentals nearby
9.0 out of 10, Wonderful, (1003)
Skiers revel in powder-filled days at this Berkshire Mountain retreat, offering cross-country trails, downhill runs, and snowboarding adventures. After exhilarating slopes, savour Indian cuisine at Mint restaurant while admiring spectacular lake sunsets from private deck views.
The price is ฿3,552
฿3,968 total
includes taxes & fees
30 Nov - 1 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
  • Ski lifts nearby
  • Snowboarding nearby
8.8 out of 10, Excellent, (690)
Mountain enthusiasts thrive at this riverfront haven featuring an indoor heated pool perfect for après-ski relaxation. Situated near Ski Butternut, the hotel offers convenient access to snowboarding, skiing, and hiking trails. Adventurous days end with plush pillowtop beds and complimentary breakfast.
The price is ฿3,314
฿3,702 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Quality Inn

2.5 star property
Lee
  • Breakfast included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Parking available
  • Housekeeping
8.4 out of 10, Very good, (1000)
Mountain enthusiasts savour slope-ready accommodation with premium bedding and in-room refrigerators, ideal for storing snacks after exhilarating runs. Situated minutes from area ski destinations, this hotel offers complimentary continental breakfast before adventurous winter days.
The price is ฿2,831
฿3,162 total
includes taxes & fees
1 Dec - 2 Dec
Quality Inn

Berkshire Mountain Lodge

3.0 star property
Pittsfield
  • Ski equipment rentals nearby
  • Hot tub
9.0 out of 10, Wonderful, (747)
Skiers thrive at this mountain retreat offering proximity to Bousquet Ski Area and equipment rentals. Spacious rooms feature full kitchens for après-ski meals, while the hot tub soothes tired muscles. Adventure continues with nearby hiking trails, snow tubing, and ziplining opportunities.
Berkshire Mountain Lodge
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.

Top Hillsdale Hotel Reviews