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) 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 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 $103 total per night from Sep 1 to Sep 2
$103 total
per night
Sep 1 - Sep 2
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 ...
Quality Inn Great Barrington
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
The price is $124 total per night from Sep 1 to Sep 2
$124 total
per night
Sep 1 - Sep 2
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 ...
8.6/10 Excellent! (597 reviews)
"Great location. Functional and affordable. Pet friendly."

Reviewed on Aug 6, 2026

The Little Lion
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 $169 total per night from Sep 7 to Sep 8
$169 total
per night
Sep 7 - Sep 8
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
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.
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Monument Mountain Reservation and Art ...
9.6/10 Exceptional! (23 reviews)
"Very pleasant stay. We would love to come back."

Reviewed on Aug 7, 2026

Cozy Riverside Berkshires Retreat
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy private pools, a garden, and laundry facilities. Popular attractions W.E.B. Du Bois Boyhood Homesite and ...
10/10 Exceptional! (59 reviews)
"Beautiful house. Super easy check-in and great communication communications with a host. House beautifully decorated and well appointed. Beautiful grounds. Everything I promises to be. Best VRBO I’ve ever stayed at. Will be coming back."

Reviewed on Jul 25, 2026

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake

Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake

Great Barrington MA
Stay at this apartment in Great Barrington. Enjoy free WiFi, a garden, and patios. Popular attractions Lake Mansfield Park and Housatonic River are located ...
10/10 Exceptional! (2 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"

Reviewed on Jul 17, 2026

Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake
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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