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 $103 per night from May 18 to May 19
CA $103
CA $116 total
May 18 - May 19
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 ...
8.4/10 Very Good! (1,003 reviews)
Staff was very friendly, room was clean

Reviewed on Apr 27, 2026

Quality Inn Great Barrington
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
The price is CA $86 per night from Apr 29 to Apr 30
CA $86
CA $96 total
Apr 29 - Apr 30
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! (845 reviews)
This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires.

Reviewed on Apr 26, 2026

Monument Mountain Motel
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
The price is CA $150 per night from Apr 29 to Apr 30
CA $150
CA $168 total
Apr 29 - Apr 30
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! (556 reviews)
A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on ...

Reviewed on Apr 20, 2026

The Little Lion
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 National Shrine of the Divine Mercy and ...
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!
Amazing  2-bedroom apartment sunny and quiet in Great Barrington

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington MA
Stay at this apartment in Great Barrington. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Housatonic River and Housatonic ...
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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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