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, Rte 7 and Main Street, Great Barrington, MA
The price is AU$156 per night from 28 Sept to 29 Sept
AU$156
28 Sept - 29 Sept
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 ...
8.2/10 Very Good! (1,000 reviews)
"Room very comfortable and clean; appreciated free wifi, breakfast, coffee, iron and hairdryer. But best of all, the warm welcome that Brian at the Reception Desk gave us and all the information he gave about Great Barrington, excellent recommendations on dining spots and, especially, telling us about ..."

Reviewed on 8 Sep. 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 AU$208 per night from 28 Sept to 29 Sept
AU$208
28 Sept - 29 Sept
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 helpful staff and the ...
8.8/10 Excellent! (657 reviews)
"Friendly knowledgeable helpful staff"

Reviewed on 24 Aug. 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 AU$267 per night from 18 Sept to 19 Sept
AU$267
18 Sept - 19 Sept
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 helpful staff and the ...
9.2/10 Wonderful! (734 reviews)
"It has a great location - lobby area and breakfast room look nicely updated. The room was decent but thankfully with better lighting than other Fairfield Inns I’ve stayed in. The front desk employee at check in and breakfast room attendant were very friendly and helpful The only disappointment was ..."

Reviewed on 2 Sep. 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.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located ...
10/10 Exceptional! (26 reviews)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, ..."

Reviewed on 29 Jul. 2025

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
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
Stay at this vacation home in Great Barrington. Enjoy private pools, a water park, and a garden. Popular attractions W.E.B. Du Bois Boyhood Homesite and Mahaiwe ...
10/10 Exceptional! (54 reviews)
Perfect stay!
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. ..."

Reviewed on 20 Apr. 2025

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

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (128 reviews)
"The property is beautiful and very walkable, and well-located with Tanglewood, The Mount, Shakespeare & Co and downtown Lenox extremely nearby. Onsite amenities such as clubhouse, tennis courts and pool are convenient and the individual units are nicely laid out. The property is a bit older and could ..."

Reviewed on 3 Sep. 2025

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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