Find Ski Hotels in Western Massachusetts, MA

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Western Massachusetts Ski Hotels

Top Western Massachusetts Ski Hotels

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Snowboarding nearby
  • Ski passes
  • Hot tub
9.2 out of 10, Wonderful, (1005)
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 ₩112,617
₩125,793 total
includes taxes & fees
Dec 4 - Dec 5
The Yankee, Trademark Collection by Wyndham

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, (1001)
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 ₩137,157
₩153,203 total
includes taxes & fees
Nov 25 - Nov 26
Best Western Plus Berkshire Hills Inn & Suites

Shaker Mill Inn

2.5 star property
West Stockbridge
  • Breakfast included
  • Parking included
  • Free WiFi
  • Housekeeping
9.6 out of 10, Exceptional, (436)
Mountain escapades flourish at this charming inn, where skiing enthusiasts find pristine trails just steps away. Nestled in West Stockbridge, active travelers enjoy cross-country and downhill skiing before returning to peaceful accommodations. Complimentary breakfast fuels outdoor adventures in this serene county setting.
The price is ₩184,871
₩202,804 total
includes taxes & fees
Dec 2 - Dec 3
Shaker Mill Inn

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, (696)
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 ₩157,598
₩176,037 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (962)
Mountain adventures begin at this ski-friendly hotel where cross-country trails and downhill slopes await nearby. After exhilarating snow activities, guests revitalize in the heated indoor pool and health club. The onsite restaurant serves delicious meals perfect for refueling between winter excursions.
The price is ₩131,499
₩146,884 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Vacation Village in the Berkshires

3.0 star property
Williamstown
  • Skiing lessons nearby
8.8 out of 10, Excellent, (2138)
Mountainside relaxation awaits after downhill adventures, with indoor and outdoor pools offering post-ski rejuvenation. Families appreciate the playground, arcade room, and sports courts while savoring spectacular Berkshire views. Spacious accommodations feature fireplaces perfect for warming up after exhilarating mountain experiences.
The price is ₩108,651
₩137,459 total
includes taxes & fees
Nov 29 - Nov 30
Vacation Village in the Berkshires

The Red Lion Inn

3.5 star property
Stockbridge
  • Snowboarding nearby
  • Skiing lessons nearby
  • Ski equipment rentals nearby
8.8 out of 10, Excellent, (1002)
Mountain adventures begin at this charming historic hotel, where skiers access cross-country and downhill trails nearby. After exhilarating snow activities, soak in the outdoor hot tub, enjoy excellent dining at 3 restaurants, or unwind by the lobby fireplace.
The price is ₩219,459
₩310,939 total
includes taxes & fees
Dec 15 - Dec 16
The Red Lion 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, (1000)
Skiers revel in powder-filled days at this Berkshire Mountain retreat, offering cross-country trails, downhill runs, and snowboarding adventures. After exhilarating slopes, savor Indian cuisine at Mint restaurant while admiring spectacular lake sunsets from private deck views.
The price is ₩155,893
₩174,133 total
includes taxes & fees
Dec 22 - Dec 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
  • Snowboarding nearby
  • Ski passes
  • Ski equipment rentals nearby
9.2 out of 10, Wonderful, (1000)
Mountain adventure beckons from this ski-friendly retreat with easy access to cross-country and downhill skiing. Following powder-filled days, guests rejuvenate in the indoor pool before retiring to spotlessly clean, spacious rooms. Complimentary breakfast fuels tomorrow's snow explorations.
The price is ₩163,156
₩182,245 total
includes taxes & fees
Dec 1 - Dec 2
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Springfield/Downtown

2.5 star property
South End
  • Ski lifts nearby
  • Snowboarding nearby
8.6 out of 10, Excellent, (1001)
Mountain enthusiasts flock to this Springfield haven, where skiing, snowboarding, and cross-country trails await nearby. After exhilarating slopes, swimmers retreat to the indoor pool while fitness buffs enjoy the 24-hour gym. Clean, spacious rooms provide perfect recovery before complimentary breakfast.
The price is ₩152,001
₩172,445 total
includes taxes & fees
Dec 11 - Dec 12
Hampton Inn & Suites Springfield/Downtown
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 Western Massachusetts Hotel Reviews

Explore a world of travel with Expedia