Great Barrington Travel Guide

Tourist Guide

Great Barrington
Great Barrington
Great Barrington which includes central business district
Great Barrington which includes central business district, café lifestyle and outdoor eating
Great Barrington featuring 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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
The price is NZ$124 per night from 23 Mar to 24 Mar
NZ$124
23 Mar - 24 Mar
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 ...
8.4/10 Very Good! (1,001 reviews)
Everything was great except the toilet tube. That was dirty

Reviewed on 25 Feb 2026

Quality Inn
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 NZ$192 per night from 11 Mar to 12 Mar
NZ$192
11 Mar - 12 Mar
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! (739 reviews)
Nice and responsive

Reviewed on 23 Feb 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd Great Barrington MA
The price is NZ$285 per night from 29 Mar to 30 Mar
NZ$285
29 Mar - 30 Mar
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 ...
9.4/10 Exceptional! (767 reviews)
Room spotless and staff were great

Reviewed on 8 Feb 2026

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.
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! (31 reviews)
Great house with plenty of bedrooms and space! Perfect location for a ski weekend.

Reviewed on 16 Jan 2026

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 ...
Pet Friendly Riverfront Home in Great Barrington
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 ...
9.6/10 Exceptional! (43 reviews)
The location was wonderful. The host was very friendly and informative.

Reviewed on 10 Feb 2026

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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