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Top The Berkshires Ski Resorts and Hotels

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is $115 per night
$115
includes taxes & fees
$105 per night
Jan 5 - Jan 6, 2025
Free WiFi in public areas is available at this bed & breakfast. Take advantage of the free self parking.
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $141 per night
$141
includes taxes & fees
$127 per night
Jan 5 - Jan 6, 2025
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
The price is $178 per night
$178
includes taxes & fees
$159 per night
Dec 25 - Dec 26
A full-service spa and an indoor pool are featured at this smoke-free hotel. There's fun for all ages with a playground and an arcade/game room, and families ...
Club Wyndham Bentley Brook

Club Wyndham Bentley Brook

3 out of 5
1 Corey Road, Hancock, MA
Get rates
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free hotel. Take advantage of ski storage on site, and enjoy snowboarding. Enjoy the indoor ...
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
The price is $108 per night
$108
includes taxes & fees
$97 per night
Dec 30 - Dec 31
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
Berkshire Valley Inn

Berkshire Valley Inn

2.5 out of 5
2541 Hancock Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
The price is $106 per night
$106
includes taxes & fees
$97 per night
Dec 23 - Dec 24
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. If you want to take your pet along, this ...
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
The price is $74 per night
$74
includes taxes & fees
$67 per night
Jan 1 - Jan 2, 2025
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
The price is $216 per night
$216
includes taxes & fees
$197 per night
Jan 1 - Jan 2, 2025
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks ...
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
The price is $207 per night
$207
includes taxes & fees
$189 per night
Jan 1 - Jan 2, 2025
Ski-in/ski-out access, 2 restaurants, and 2 outdoor tennis courts are all featured at this smoke-free condo resort. Take advantage of ski lessons, ski rentals ...
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
The price is $94 per night
$94
includes taxes & fees
$85 per night
Dec 29 - Dec 30
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Free Cancellation
The price is $111 per night
$111
includes taxes & fees
$99 per night
Jan 5 - Jan 6, 2025
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
The price is $77 per night
$77
includes taxes & fees
$69 per night
Dec 29 - Dec 30
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and dry cleaning are also on offer.
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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.

Ski Resorts in The Berkshires

It’s that time of the year—the mountains are calling and you are ready to hit the slopes. There’s no better place than ski hotels in The Berkshires. With access to various places to ski, from bunny hills for the newbies to black diamonds for the experts, The Berkshires ski resorts are your best bet to enjoy some wintry fun.

If you're a beginner skier and want to start with a few trips down the bunny slopes, see if your The Berkshires ski hotel or the nearby facilities offer lessons. If you're a veteran on the slopes, take the chair lift up to the top of the mountain and take in the views as you slalom down the fresh snow. After a full day on the slopes, retreat to your The Berkshires ski resort to warm up. Take a dip in the hot tub on property, drink some cocktails at the lobby bar to warm you up or get cozy in your hotel room and order room service. 

Travelocity is here to help you find the best deals on The Berkshires ski hotels and resorts, so you can hit the ski lift without breaking the bank! Book today and Wander Wisely.

The Berkshires hotels essential information

Accommodation
1,021 hotels
Lowest Price
$74
Highest Price
$216
Popular hotels
Vacation Village in the Berkshires, The Yankee, Trademark Collection by Wyndham, Berkshire Valley Inn, Jiminy Peak Mountain Resort, Hampton Inn & Suites Berkshires-Lenox, Monument Mountain Motel, Shaker Mill Inn, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Quality Inn, Club Wyndham Bentley Brook, Travelodge by Wyndham Great Barrington Berkshires

Recent The Berkshires hotel reviews by fellow wanderers

The Red Lion Inn

The Red Lion Inn

5 out of 5
Posted 17 hours ago
Travelocity Verified Review
"Lively plae"
A verified traveler stayed at The Red Lion Inn
The Red Lion Inn