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 €64 per night from 30 Apr to 1 May
€64
30 Apr - 1 May
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)
I like this hotel for the great location, breakfast included, and clean adequate rooms. The staff are wonderful. Very well priced.

Reviewed on 12 Apr 2026

Quality Inn Great Barrington
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 €97 per night from 23 Apr to 24 Apr
€97
23 Apr - 24 Apr
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! (755 reviews)
Yes

Reviewed on 13 Apr 2026

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
The price is €57 per night from 23 Apr to 24 Apr
€57
23 Apr - 24 Apr
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 and the clean rooms in their ...
9/10 Wonderful! (840 reviews)
We didn’t get to check in with staff. An envelope with my name on it and a key. Bathroom shower is small and tight. Rooms are okay clean wise.

Reviewed on 12 Apr 2026

Monument Mountain Motel
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 holiday home in Great Barrington. Enjoy free Wi-Fi, 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 15 Apr 2026

Cozy Riverside Berkshires Retreat
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 ...
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! (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!
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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