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.

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$832 per night from 14 Jan to 15 Jan
HK$832
HK$929 total
14 Jan - 15 Jan 2026
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! (709 reviews)
Clean, everyone there was so sweet! Great breakfast

Reviewed on 20 Dec 2025

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
The price is HK$588 per night from 12 Jan to 13 Jan
HK$588
HK$657 total
12 Jan - 13 Jan 2026
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)
My go to place for my ski weekends

Reviewed on 20 Dec 2025

Quality Inn
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is HK$1,960 per night from 26 Jan to 27 Jan
HK$1,960
HK$2,449 total
26 Jan - 27 Jan 2026
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 ...
9.4/10 Exceptional! (15 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on 29 Nov 2025

Prospect 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! (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 ...
9.2/10 Wonderful! (5 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
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! (54 reviews)
We had a great time at this house. The second living/play room was great for the 8 kids we had with us as it gave them a separate space to play. The large front and back yards also provided ample space to get outdoors. The house was clean and well suited for our large group.

Reviewed on 10 Dec 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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