Find Ski Hotels in Hillsdale, NY

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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, (116)
The Brooks Motel

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Snowboarding nearby
  • Ski passes
  • Hot tub
9.2 out of 10, Wonderful, (1011)
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 AED 229
AED 256 total
includes taxes & fees
7 Dec - 8 Dec
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, (1004)
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 AED 343
AED 384 total
includes taxes & fees
2 Dec - 3 Dec
Best Western Plus Berkshire Hills Inn & Suites

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, (1006)
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 AED 390
AED 436 total
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 AED 384
AED 422 total
includes taxes & fees
2 Dec - 3 Dec
Shaker Mill Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Snowboarding nearby
  • Hot tub
9.2 out of 10, Wonderful, (64)
Skiers discover winter bliss near this Berkshires hotel with easy access to Bousquet Ski Area and cross-country trails. After snowy adventures, soak in the hot tub, swim indoors, or venture to nearby Tanglewood. A complimentary breakfast fuels each morning's mountain expedition.
The price is AED 350
AED 391 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires 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, (974)
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 AED 341
AED 381 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
7.6 out of 10, Good, (827)
The price is AED 290
AED 324 total
includes taxes & fees
1 Dec - 2 Dec
Howard Johnson by Wyndham Lenox

Monument Mountain Motel

2.5 star property
Great Barrington
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • Microwave
  • Extra beds/cribs
9.0 out of 10, Wonderful, (801)
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

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Microwave
7.6 out of 10, Good, (560)
The price is AED 275
AED 308 total
includes taxes & fees
1 Dec - 2 Dec
Travelodge by Wyndham Great Barrington Berkshires
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.

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