Great Barrington, MA

Travel Guide

A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.
A street lined with parked cars, trees, and buildings including a church and a bank.
A street scene with a restaurant named 'Baba Louie's' and a car parked on the side of the road.
A large stone church with a tall bell tower and arched windows.
A brick building with a white door, arched windows, and a clock tower.

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 center 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 Center. 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 kilometers) of scenic 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 kilometers) 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 center 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 NT$4,269 per night from Jul 22 to Jul 23
NT$4,269
NT$4,769 total
Jul 22 - Jul 23
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,005 reviews)
"Great experience. Friendly staff. Easy walk to town."

Reviewed on 2026/7/18

Quality Inn Great Barrington
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
The price is NT$4,074 per night from Jul 22 to Jul 23
NT$4,074
NT$4,550 total
Jul 22 - Jul 23
includes taxes & fees
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Little Lion
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
The price is NT$13,531 per night from Aug 19 to Aug 20
NT$13,531
NT$16,197 total
Aug 19 - Aug 20
includes taxes & fees
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,012 reviews)
"Very good value if you can find a deal. Large rooms and clean but a bit rough around edges. Also some minor maintence issues. I would stay again if price was right. kitchen well equipped and bed comfortable. Not much in way of outdoor amenities- no real place for a walk but a few chairs spread around. ..."

Reviewed on 2026/7/18

Berkshire Mountain Lodge
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20 Hudson NY
Book a stay at this business-friendly aparthotel in Hudson. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions FASNY Museum of Firefighting ...
9.2/10 Wonderful! (158 reviews)
"Great place to stay close to Hudson. Steven is very welcoming. The room is clean, comfortable and convenient. I’d stay there again."

Reviewed on 2026/7/18

Micosta Leisure Inn
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and National Shrine of the ...
8.6/10 Excellent! (142 reviews)
"The place is on beautiful grounds & the units are spacious & clean & you have everything you need. My big complaint is that the indoor & outdoor pools were closed, in the middle of a hot summer week, awaiting an inspection by the Bd. of Health. Thus should have been communicated to us before (or ..."

Reviewed on 2026/7/14

The Ponds at Foxhollow
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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