10 Best Ski Resorts In The Berkshires, Massachusetts - Updated 2023


Situated in the western part of Massachusetts, the Berkshires is a haven for outdoor enthusiasts. Whether you plan to visit in the summer or winter, this region offers plenty of activities to keep you occupied. You can indulge in hiking, skiing, snowmobiling, and camping here. It also offers plenty of stunning towns, each with its own charm. Visit Pittsfield, which is the most populated town in the area and known for its historical attractions, such as Herman Melville’s Arrowhead and the Berkshire Museum. Great Barrington is also a great destination, known as one of the most beautiful towns in the region. It is home to Monument Mountain, which is perfect for hiking, and Ski Butternut. If you are seeking a comfortable holiday filled with exciting outdoor adventures in this region, check out these best ski resorts in the Berkshires, Massachusetts.

1. Jiminy Peak Mountain Resort, Hancock (from USD 120)

Perfect for outdoor enthusiasts, Jiminy Peak Mountain Resort has a lot to offer its visitors in any season. This three-star property offers spacious rooms and apartments that come with a full bath, an airy living area, and a fully equipped kitchen, so you can conveniently prepare your own meals during your stay. You can purchase lift tickets at the resort if you want to go skiing. Skiing and snowboarding lessons for beginners are also offered here.

Jiminy Peak Mountain Resort

Wifi Available

Address: 37 Corey Road
Accommodates: 8

Parking Restaurant Meeting/banquet facilities Bar 24-hour front desk Tennis court Sauna Fitness centre

Accommodations near ski area

2. Club Wyndham Bentley Brook, Hancock (from USD 87)

Club Wyndham Bentley Brook is a three-star property that is suitable for couples and families. It offers spacious and air-conditioned suites that are equipped with a cable TV for entertainment and two modern baths with free toiletries. You can enjoy access to free WiFi throughout the premises. The game room has a pool table, and there are tennis courts on site.

If you are seeking some outdoor recreation, you can enjoy skiing and snowboarding nearby. The well-groomed trails of Jiminy Peak Mountain Resort are just a stone’s throw away. The hotel also has a hot tub and sauna to work out those tired muscles.

Club Wyndham Bentley Brook

Wifi Available

Address: 1 Corey Road
Accommodates: 10

Parking Tennis court Sauna Fitness centre Non-smoking rooms Laundry Facilities for disabled guests Skiing

3. Vacation Village in the Berkshires, Hancock (from USD 155)

Situated in a quiet area in Hancock overlooking the rolling hills, Vacation Village in the Berkshires offers cozy rooms with a kitchen for easy meal preparation, a TV to keep guests entertained, and a coffee maker. It is just 1 km (0.6 mi) from Jiminy Peak ski area, where you can enjoy skiing, snowshoeing, and snowboarding.

After a day in the powder, you can relax in the pool or curl up near the outdoor fireplace. Those who wish to enjoy a proper workout can take advantage of the well-equipped fitness center on site.

Vacation Village in the Berkshires

Wifi Available

Address: 276 Brodie Mountain Road
Accommodates: 8

Parking 24-hour front desk Fitness centre Golf course (within 3 km) Garden Terrace Non-smoking rooms Business centre

4. Hotel on North, Pittsfield (from USD 164)

A simple hotel in Pittsfield, Hotel on North features roomy accommodations that come with a private bathroom, a minibar for unwinding, and a wardrobe for storing your garments. Family rooms are also offered here, suitable for those who are planning to bring their kids along.

This property is a 20-minute drive from Jiminy Peak Mountain Resort, perfect for those who wish to go skiing. Ski passes are available on site, as is ski storage and equipment. There is a business center on site, in case you need to catch up on work during your stay.

Hotel on North

Wifi Available

Address: 297 North Street
Accommodates: 4

Parking Pets allowed Room service Meeting/banquet facilities Bar 24-hour front desk Non-smoking rooms Business centre

5. Berkshire Valley Inn, North Hancock (from USD 84)

Set in North Hancock, Berkshire Valley Inn boasts a lovely outdoor pool with a shallow end and gorgeous views of the lush surroundings. This property is a great accommodation option if you want to enjoy some outdoor activities, like skiing, as it is situated less than 10 minutes’ away from Jiminy Peak Mountain Resort. After an adventurous day, you can take advantage of the picnic area or the sun deck to relax. Pets are welcome here at an extra charge.

Berkshire Valley Inn

Wifi Available

Address: 2541 Hancock Road
Accommodates: 6

Parking Pets allowed Non-smoking rooms Skiing Family rooms Breakfast in the room Free parking Internet services

6. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel (from USD 111)

This four-star hotel found in Pittsfield is pet-friendly and offers easy access to the Appalachian Trail. Plus, the ski areas of Bousquet Mountain, known for snowboarding and cross-country skiing, are just a seven-minute drive away from the property. You can purchase ski passes at the hotel.

Each room comes with free WiFi access, a flat-screen TV, a work desk, and a private bathroom. You can have a relaxing massage at the spa after a fun-filled day outdoors. The indoor swimming pool welcomes guests of all ages and is open all year round.

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Wifi Available

Address: 1 West Street
Accommodates: 6

Restaurant Pets allowed Meeting/banquet facilities Bar 24-hour front desk Tennis court Fitness centre Golf course (within 3 km)

7. Lanesboro Country Inn, Lanesborough (from USD 95)

Situated just 5.7 km (3.5 mi) away from Jiminy Peak Mountain Resort, Lanesbory Country Inn is perfect for travelers who are seeking a wonderful skiing holiday in the center of the Berkshires. There’s private storage for skis on site, and ski equipment is also available for rent.

Free WiFi can be accessed throughout the property, so feel free to update your socials during your stay. The rooms are equipped with a microwave and a fridge, allowing you to easily prepare and store your food and beverages. There’s also a flat-screen TV in each room and it comes with HBO access to keep guests occupied.

Lanesboro Country Inn

Wifi Available

Address: 499 South Main Street
Accommodates: 4

Parking Pets allowed Golf course (within 3 km) Non-smoking rooms Fishing Skiing Family rooms Free parking

8. Berkshire Inn, Pittsfield (from USD 79)

Conveniently situated in the heart of the Berkshires, Berkshire Inn is less than a 10-minute drive from the Bousquet Mountain ski area. After a day on the slope, unwind in the outdoor pool. All rooms here feature a TV with cable channels, a microwave, and an en-suite bathroom for convenience.

A delicious continental breakfast is served daily in the lobby. Should you have any concerns, you can approach the staff at the 24-hour front desk. You also have access to WiFi at no extra charge, so you can conveniently keep your socials updated.

Berkshire Inn

Wifi Available

Address: 150 West Housatonic Street
Accommodates: 2

Parking 24-hour front desk Non-smoking rooms Family rooms Free parking Internet services Heating Fax/photocopying

9. Best Western Plus Berkshire Hills Inn & Suites, Pittsfield (from USD 114)

Featuring a well-equipped gym and hot tub, Best Western Plus Berkshire Hills Inn & Suites can ensure guests a relaxing and comfortable holiday in Pittsfield. All rooms and suites come with a cable TV, tea- and coffee-making facilities, and a spacious bathroom.

For your convenience, essentials such as towels and bathing products are provided. The Jiminy Peak ski lift is 30.6 km (19 mi) away from the property, making it ideal for travelers who wish to engage in outdoor activities, such as skiing.

Best Western Plus Berkshire Hills Inn & Suites

Wifi Available

Address: 1350 West Housatonic Street
Accommodates: 6

Parking Meeting/banquet facilities 24-hour front desk Fitness centre Non-smoking rooms Business centre Facilities for disabled guests Family rooms

10. Howard Johnson by Wyndham Lenox (from USD 69)

Featuring simple yet cozy rooms, Howard Johnson by Wyndham Lenox is a two-star property that offers beautiful mountain vistas. It has an outdoor pool, where you can enjoy a relaxing swim in your leisure time. Bousquet Mountain ski area is just 1 km (0.6 mi) away from the property, and there is also a golf course nearby.

Free continental breakfast is served daily for your convenience. Vending machines are available here for some quick snacks. If you are looking to sample the local cuisine, there are three restaurants within walking distance.

Howard Johnson by Wyndham Lenox

Wifi Available

Address: 462 Pittsfield Road
Accommodates: 4

Parking 24-hour front desk Golf course (within 3 km) Garden Non-smoking rooms Facilities for disabled guests Skiing Family rooms

Have a great skiing holiday in the Berkshires

The Berkshires in Massachusetts is known for its outdoor adventures and is a paradise for winter sports enthusiasts. Here, you can indulge in skiing, tubing, snowboarding, and other activities. For a memorable stay in the region, book one of the above listed ski resorts.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

An avid traveler, Martina aims to visit as many countries as she can. This caféphile admires things that can take her to different places, hence her love for books, baking, and writing. She is...Read more

 Want to contribute as a Local Expert?
Explore The Berkshires
Looking for accommodation?
Good things are meant to be shared!