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, such as family resorts, to keep you occupied. You can indulge in hiking, skiing, snowmobiling, and camping at the glamping spots 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 seek a comfortable holiday filled with exciting outdoor adventures in this region, read about these best ski resorts in the Berkshires, Massachusetts.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to ski slopes and equipment. The image galleries get refreshed with the latest updates regularly. They were last updated on May 28, 2024.
1. Jiminy Peak Mountain Resort, Hancock (from USD 174)
Reasonable off-peak value, but higher than nearby options
Mountain adventure park, heated pool, spacious suites with kitchenettes
Beautiful Berkshires setting, walkable to attractions, but some rooms have accessibility issues
On-site restaurant, country store with breakfast options, but limited dining availability
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
Address: 37 Corey Road
344 meters (0.3 ft) from Jiminy Peak Mountain Resort
Accommodations near ski area
2. Charming abode with access to a communal pool, Hancock (from USD 723)
This charming abode is less than 0.1 miles (0.16 kilometers) from the Jiminy Peak Mountain Resort. Step inside and relax in the living room with a 65-inch high-definition Smart TV and a Sonos Playbar. On chilly evenings, cozy up by the fireplace. You can also enjoy the views from the deck. If you want to unwind, the bathroom features a jetted tub perfect for relaxation.
It also features air conditioning and heating, ensuring you are comfortable anytime. The communal pool is the perfect place to cool off and enjoy when the weather is warm.
For those who love to ski, the house is ideally situated just for a quick walk through the woods to the Grouse Run ski trail; easy access allows you to spend your days skiing and snowboarding to your heart’s content.
Top guest reviews
Amenities & Room:
the house is beautiful and very comfortable particularly for our multi generational groupCleanliness:
the house was beautiful and clean - in a lovely settingHost:
the host is fantastic very helpful- the best: the host was fantastichouse is amazing and easy to communicate with ownerour host howard was so attentive and helpfulthe kitchen was very well stocked and the owner was super to work withRead more reviewsLocation:
second time staying here and it was delightful the house has everything you’ll need and has the perfect locationkids had lots of fun at mountain adventure parkvery comfortable place to stay
3. Lovely property with a bathtub, Hancock (from USD 270)
This property offers a fantastic getaway for guests who enjoy skiing, as it is conveniently located near the Jiminy Peak Mountain Resort. Guests can take advantage of the nearby ski trails and lifts for an exhilarating outdoor experience. It has air conditioning and heating to ensure a comfortable stay, regardless of the weather. There is also a TV with satellite and cable channels and a DVD player for entertainment.
For relaxation, it features a bathtub for a soothing soak after a long day. Guests can also enjoy the indoor and outdoor heated pools on the premises and a game room for entertainment.
An onsite fitness center is available for those looking to stay active during their stay. For relaxation, guests can indulge in the sauna or the outdoor gazebo with a hot tub, perfect for unwinding and taking in the stunning views of the surrounding area.
Top guest reviews
Cleanliness:
the condo was clean and well equipped for what we neededthe condo was great - updated clean and well-equippedbentley brook is a great location nice clean and very quiet buildingclean efficient ski on/off propertyHost:
susan was very helpful with questions that we had prior to our weekendRead more reviewsLocation:
great location and very comfyloved this property and the location—it is literally ski in / ski out and perfect for a family vacationbut overall a nice place for a quick ski trip if skiing is all you are looking forperfect place to stay at jiminy peak
4. Club Wyndham Bentley Brook, Hancock (from USD 87)
Great value for spacious, well-equipped suites in a prime location.
Abundance of family-friendly activities, pools, and a game room.
Convenient access to ski resorts and natural attractions in the Berkshire mountains.
Limited dining options on-site, but well-stocked kitchens in the suites provide convenience.
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 snowboarding and nearby best skiing in Berkshires. 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
Address: 1 Corey Road
169 meters (0.2 ft) from Jiminy Peak Mountain Resort
5. Vacation Village in the Berkshires, Hancock (from USD 157)
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 the Jiminy Peak ski area in Massachusetts, 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
Address: 276 Brodie Mountain Road
1.02 km (0.7 mi) from Jiminy Peak Mountain Resort
6. Hotel on North, Pittsfield (from USD 149)
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 in the ski mountains of Massachusetts. 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
Address: 297 North Street
11.86 km (7.4 mi) from Jiminy Peak Mountain Resort
7. Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel (from USD 132)
This four-star hotel found in Pittsfield is pet-friendly and offers easy access to the Appalachian Trail. Plus, the Bousquet Mountain’s ski areas in the Berkshires, known for snowboarding and cross-country skiing, are just a seven-minute drive 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
Address: 1 West Street
12.31 km (7.7 mi) from Jiminy Peak Mountain Resort
8. Berkshire Inn, Pittsfield (from USD 100)
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
Address: 150 West Housatonic Street
12.61 km (7.9 mi) from Jiminy Peak Mountain Resort
9. Best Western Plus Berkshire Hills Inn & Suites, Pittsfield (from USD 125)
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
Address: 1350 West Housatonic Street
13.63 km (8.5 mi) from Jiminy Peak Mountain Resort
10. Howard Johnson by Wyndham Lenox (from USD 88)
Affordable rates for spacious rooms, but some issues with overcharging and pricing accuracy.
Convenient location, quiet rooms, and friendly staff, but some amenities like pool and breakfast were lacking or underwhelming.
Centrally located with easy access to attractions, dining, and shopping, but some guests found the immediate area less appealing.
Simple continental breakfast with room for improvement, but nearby dining options available for convenience.
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
Address: 462 Pittsfield Road
17.13 km (10.7 mi) from Jiminy Peak Mountain Resort
11. Berkshire Valley Inn, North Hancock (from USD 129)
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
Address: 2541 Hancock Rd
5.38 km (3.4 mi) from Jiminy Peak Mountain Resort
12. 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
Address: 499 South Main Street
5.56 km (3.5 mi) from Jiminy Peak Mountain Resort
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.
Frequently asked questions about the best ski resorts in the Berkshires, Massachusetts
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