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 CA $131 per night from Jun 15 to Jun 16
CA $131
CA $147 total
Jun 15 - Jun 16
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,000 reviews)
"Excellent location, great low price, VERY Comfortable bed- throwback era motel. Why pay more when it’s all here!"

Reviewed on Jun 7, 2026

Quality Inn Great Barrington
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
The price is CA $123 per night from Jun 14 to Jun 15
CA $123
CA $137 total
Jun 14 - Jun 15
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (565 reviews)
"Parking is"

Reviewed on Jun 5, 2026

The Little Lion
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
The price is CA $107 per night from Jun 21 to Jun 22
CA $107
CA $120 total
Jun 21 - Jun 22
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (867 reviews)
"Room was clean and cozy, bed comfy, pillows comfy, bathroom nice and clean, plenty of towels, AC worked, and plenty of parking for two cars since we usually travel with 2 vehicles."

Reviewed on Jun 10, 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.
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Monument Mountain Reservation and Art ...
9.2/10 Wonderful! (15 reviews)
"We had the best time at Marisa's place. It was a charming and comfortable home, and, for our purposes, was an excellent location as we were on a bit of a tour to visit a few different towns where famous American authors lived. Near the house, we found good food -- Prairie Whale and Xicohtencatl Restaurant ..."

Reviewed on Jun 3, 2026

Cozy Riverside Berkshires Retreat
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

New Marlborough MA
Stay at this cottage in Great Barrington. Enjoy laundry facilities, patios, and in-room washers/dryers. Popular attractions Lake Buel and Les Trois Emme Winery ...
9.2/10 Wonderful! (44 reviews)
"Could not have been more relaxing or enjoyable."

Reviewed on Oct 14, 2025

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located ...
10/10 Exceptional! (32 reviews)
"As noted in the listing, the house is on the older side, but it is very well kept up, the rooms were clean, the kitchen was also clean and very complete for making and serving meals. We had a group of 5 couples getting together for a reunion and had a great weekend at the Inn."

Reviewed on Apr 5, 2026

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
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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