Find & compare ski resorts in Western Massachusetts, MA from $66

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Western Massachusetts Ski Resorts and Hotels

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is $145 per night
$145
per night
May 28 - May 29
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
per night
May 30 - May 31
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 $152 per night
$152
per night
May 27 - May 28
This hotel features an indoor pool and a 24-hour gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite ...
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 $110 per night
$110
per night
May 30 - May 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 $164 per night
$164
per night
May 26 - May 27
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 $66 per night
$66
per night
May 27 - May 28
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Free Cancellation
The price is $132 per night
$132
per night
May 27 - May 28
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 ...
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
The price is $154 per night
$154
per night
May 30 - May 31
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 $85 per night
$85
per night
May 30 - May 31
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 $97 per night
$97
per night
May 30 - May 31
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 $69 per night
$69
per night
May 27 - May 28
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.
Don't see what you're looking for?
See all available properties in Western Massachusetts
View all properties
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 Western Massachusetts

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 Western Massachusetts. With access to various places to ski, from bunny hills for the newbies to black diamonds for the experts, Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts ski hotels and resorts, so you can hit the ski lift without breaking the bank! Book today and Wander Wisely.

Western Massachusetts hotels essential information

Accommodation
1,325 hotels
Lowest Price
$66
Highest Price
$164
Popular hotels
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, Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Recent Western Massachusetts hotel reviews by fellow wanderers

The Red Lion Inn

The Red Lion Inn

5 out of 5
Posted 6 days ago
Travelocity Verified Review
"Very comfortable beds. Quiet with very friendly staff. Wasn’t too thrilled with the antique bathtub, too high to step into safely for seniors. "
A verified traveler stayed at The Red Lion Inn
The Red Lion Inn

Explore more Ski Resorts and Hotels

Types of hotels

Hotels near…

Hotels by star rating

Areas of Western Massachusetts

Popular Ski Resorts and Hotels Destinations