Find ski hotels & lodging in West Stockbridge, MA

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Check availability on West Stockbridge Ski Hotels

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Nov 30 - Dec 1
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Dec 1 - Dec 2
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Top West Stockbridge Ski Hotels

Garden
Shaker Mill Inn

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.
$105 nightly
The price is $116
Dec 2 - Dec 3
Total with taxes and fees
Shaker Mill Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Snowboarding nearby
  • Ski passes
  • Hot tub
9.2 out of 10, Wonderful, (1012)
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.
$63 nightly
The price is $70
Dec 14 - Dec 15
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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.
$93 nightly
The price is $104
Dec 3 - Dec 4
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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.
$95 nightly
The price is $106
Dec 7 - Dec 8
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Restaurant
Holiday Inn & 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, (975)
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.
$93 nightly
The price is $104
Dec 3 - Dec 4
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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.
$98 nightly
The price is $109
Dec 22 - Dec 23
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

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.
$67 nightly
The price is $74
Dec 3 - Dec 4
Total with taxes and fees
Monument Mountain Motel
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
  • Breakfast included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Parking available
  • Housekeeping
8.4 out of 10, Very Good, (1003)
Mountain enthusiasts savor slope-ready accommodations 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.
$93 nightly
The price is $104
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn
Exterior
Howard Johnson by Wyndham Lenox

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)
$79 nightly
The price is $88
Dec 1 - Dec 2
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
  • Ski equipment rentals nearby
7.8 out of 10, Good, (839)
Glide down nearby slopes before returning to this spotless, peaceful motel featuring comfortable rooms with modern amenities. Situated within walking distance of Colonial Theater and Berkshire Museum, winter adventurers appreciate the convenient location and clean accommodations after exhilarating ski days.
$82 nightly
The price is $92
Dec 7 - Dec 8
Total with taxes and fees
Berkshire Inn
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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Top West Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Everything was a great experience "
Gonzalo 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

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