Great Barrington

Travel Guide

Great Barrington
Great Barrington
Great Barrington
Great Barrington
Great Barrington

Enjoy fine dining and antique shopping at this Berkshires hub, along with hiking, biking and skiing in the surrounding countryside.

Visit Great Barrington, the largest town in the southwest Berkshires, for outdoor activities. With more hotels, restaurants and services than in neighboring towns and villages, it’s an ideal weekend destination and a great base for exploring the area.

While Great Barrington oozes with colonial charm, the town is not sleepy. You’ll find plenty to see and do. Get acquainted with the town centre by strolling along Main Street and browsing numerous antique stores. Before shopping, consider converting your dollars into Berkshares. This local currency experiment is designed to strengthen the area’s economy visitors who use Berkshares receive discounts.

Later, select from the town’s great restaurants and funky bars. Great Barrington is home to many ex-New Yorkers and is a popular weekend destination for Manhattanites. Its diverse and sophisticated selection of restaurants appeals to this cultured clientele. Head to the Saturday farmers market for fresh, locally sourced produce.

Great Barrington has cultural attractions too. For drama, film and concerts, visit the Mahaiwe Performing Arts Centre. Built in 1905, this local institution is still going strong after more than a century. Enjoy an art exhibit at the Vault Gallery and look for the namesake vault with the safe door still intact from the days when the building was used as a bank.

While staying here, explore the great outdoors in a variety of ways. Head for the nearby nature reservation of Bartholomew’s Cobble, a rocky, tree-covered knoll with 6 miles (10 kilometres) ofscenic hiking trails. Just a 10-minute drive from the town, you’ll find Monument Mountain, which offers breathtaking views over the Housatonic River Valley. In winter, hit the slopes at the popular local ski resort Ski Butternut, which is 3 miles (5 kilometres) from Great Barrington.

Reach Great Barrington in about 2.5 hours from Boston or New York. Getting to and around this rural area is easiest by car. After enjoying everything the town centre offers, grab a map and head out to see the spectacular countryside.

Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
The price is S$121 per night from 25 May to 26 May
S$121
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,006 reviews)
"The room was nice, didn’t care for the smell in the room but I guess it’s normal. Room was clean. Nice area. Very cute town. Would definitely stay again. Loved the Bible in the drawer."

Reviewed on 16 May, 2026

Quality Inn Great Barrington
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
The price is S$136 per night from 11 Jun to 12 Jun
S$136
11 Jun - 12 Jun
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (561 reviews)
"Avoid this place."

Reviewed on 17 May, 2026

The Little Lion
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
The price is S$98 per night from 20 May to 21 May
S$98
20 May - 21 May
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (855 reviews)
"its dated old and it was sitll very clean every thing worked Room care was good. The microwave and the frig were nice. but got to give a thumbs down to no coffee in the rooom"

Reviewed on 17 May, 2026

Monument Mountain Motel
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.
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20 Hudson NY
Stay at this business-friendly aparthotel in Hudson. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions FASNY Museum of Firefighting ...
9.2/10 Wonderful! (146 reviews)
"I would absolutely stay here again. It was such a charming property that is run by lovely people. You can tell it’s run with care. Great value for the area."

Reviewed on 17 May, 2026

Micosta Leisure Inn
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (141 reviews)
"I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ..."

Reviewed on 9 Feb, 2026

The Ponds at Foxhollow
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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