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.

Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is AU$336 per night from 27 Jan to 28 Jan
AU$336
27 Jan - 28 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
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 AU$251 per night from 25 Jan to 26 Jan
AU$251
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 ...
9.2/10 Wonderful! (761 reviews)
Temperature of pool was cold

Reviewed on 1 Jan 2026

Fairfield Inn & Suites by Marriott Great Barrington Lenox/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 AU$143 per night from 22 Jan to 23 Jan
AU$143
22 Jan - 23 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! (723 reviews)
fine inn

Reviewed on 17 Jan 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
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 ...
9.2/10 Wonderful! (7 reviews)
Marisa's place was cozy and well-decorated. We enjoyed staying there for New Years and it was a good distance to the local downtowns while being quietly tucked away by the river.It was unclear to our party that the outdoor cats on the property lived within the rental unit until we received our check-in ...

Reviewed on 5 Jan 2026

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! (40 reviews)
Very nice and clean house with all amenities. Main Street is just around the corner, with all the shops and restaurants a 5-minute walk. Ski Butternut is a 7-minute drive. The host responds very quickly to all questions. I highly recommend stay at this house.

Reviewed on 27 Dec 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 ...
9.8/10 Exceptional! (30 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!
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.

Popular places to visit

Explore a world of travel with Expedia