Great Barrington Travel Guide

Tourist Guide

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
Great Barrington showing 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.

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
The price is NZ$167 per night from 10 Dec to 11 Dec
NZ$167
10 Dec - 11 Dec
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! (1,003 reviews)
Room was extremely clean, beds very comfortable, staff friendly. The only problem was the noisy heating system which loudly switched on and off at night preventing us from getting a good nights sleep. I would also suggest getting a room in the front of the hotel, rather than the back, since a train ...

Reviewed on 22 Nov 2025

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$212 per night from 11 Dec to 12 Dec
NZ$212
11 Dec - 12 Dec
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! (697 reviews)
Pancake machine was a hoot! However brown sugar for oatmeal was hard as rock just like the breakfast potatoes. Staff was nearby but no one refreshing or checking on breakfast entrees. Enjoyed the updates to thr room. Room 241 very nice! Fascia board near toilet roll needs repair. Overall I would ...

Reviewed on 23 Nov 2025

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$300 per night from 1 Dec to 2 Dec
NZ$300
1 Dec - 2 Dec
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! (755 reviews)
Yes

Reviewed on 21 Nov 2025

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.
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 ...
9/10 Wonderful! (4 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
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! (27 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!
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington MA
Stay at this ski holiday home in Great Barrington. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Lake Mansfield Park and Housatonic River ...
9.8/10 Exceptional! (53 reviews)
Place was cleanClose proximity to town and hikingHot tub holds 4 at a timeKitchen had great supplies but limited counter space

Reviewed on 29 Oct 2025

The Great Escape Ski Cottage w/HOT TUB @ 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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