Great Barrington, MA

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 center 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 Center. 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 kilometers) of scenic 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 kilometers) 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 center 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 ¥13,431 per night from May 26 to May 27
¥13,431
¥15,002 total
May 26 - May 27
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! (1,001 reviews)
"The staff was especially nice and helpful. The breakfast was one of the best. The music played in the breakfast room was fantastic. The location was great and very close to everything in Great Barrington. Will definitely stay there again."

Reviewed on May 20, 2026

Quality Inn Great Barrington
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is ¥15,091 per night from Jun 11 to Jun 12
¥15,091
¥16,856 total
Jun 11 - Jun 12
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (561 reviews)
"Avoid this place."

Reviewed on May 17, 2026

The Little Lion
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
The price is ¥10,865 per night from May 25 to May 26
¥10,865
¥12,136 total
May 25 - May 26
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! (856 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 May 17, 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! (14 reviews)
"Awesome location. Host was very informative and responsive."

Reviewed on Apr 15, 2026

Cozy Riverside Berkshires Retreat
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!
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough MA
Book a stay at this family-friendly cottage in Great Barrington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Lake Buel and Les Trois ...
9.6/10 Exceptional! (23 reviews)
"It was a great stay!"

Reviewed on May 20, 2026

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
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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