Great Barrington

Travel Guide

Great Barrington
Great Barrington featuring central business district
Great Barrington which includes café lifestyle, city views and outdoor eating
Great Barrington featuring a church or cathedral
Great Barrington which includes a church or cathedral

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.

Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is HK$1,963 per night from 26 Jan to 27 Jan
HK$1,963
HK$2,454 total
26 Jan - 27 Jan
includes taxes & fees
Stay at this hotel in Great Barrington. Enjoy free Wi-Fi, free parking and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
9.6/10 Exceptional! (18 reviews)
Wonderful stay - the property becomes a beautiful winter wonderland in December! Cabin was warm and well-designed, sauna was amazing and easily accessible all day, the staff was friendly, super responsive and drove us around the property when needed. Would recommend and plan to comeback!

Reviewed on 30 Dec 2025

Prospect Berkshires
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
The price is HK$764 per night from 25 Jan to 26 Jan
HK$764
HK$853 total
25 Jan - 26 Jan
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 helpful staff and the clean ...
8.8/10 Excellent! (715 reviews)
Very clean. Nice staff

Reviewed on 29 Dec 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
The price is HK$857 per night from 6 Jan to 7 Jan
HK$857
HK$957 total
6 Jan - 7 Jan
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 ...
8.4/10 Very Good! (547 reviews)
Perfect for pets

Reviewed on 24 Dec 2025

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.
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 Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Housatonic River and Housatonic ...
9.4/10 Exceptional! (39 reviews)
Everything was perfect. We hope it’s available next time we visit.

Reviewed on 29 Nov 2025

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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 holiday home in Great Barrington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located ...
10/10 Exceptional! (28 reviews)
The Turning Point stay was excellent in every respect. We had a large group (11) and all had great sleeping locations, some with ensuite bathrooms, all in short distance to them. Kitchen was awesome for large group cooking and service. Nothing lacking! Location great for Great Barrington attractions, ...

Reviewed on 20 Oct 2025

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington MA
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Monument Mountain Reservation and Art et ...
9.4/10 Exceptional! (6 reviews)
Amazing cosy property. The berkshires are beautiful and Marisa was a great host. Thank you for having us!

Reviewed on 9 Nov 2025

Pet Friendly Riverfront Home 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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