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Great Barrington Vacation Packages

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.


Top Hotel Deals

See all 143 Hotels in Great Barrington
£90
Fairfield Inn and Suites by Marriott Lenox Great Barrington

Fairfield Inn and Suites by Marriott Lenox Great Barrington

249 Stockbridge Rd, Great Barrington
4.4
of 5, from 60 reviews
2.5 out of 5.0

This family-friendly Great Barrington hotel is located in the mountains, within 2 mi (3 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. Ski Butternut is 2.5 mi (4.1 km) away.

£67
Days Inn Great Barrington

Days Inn Great Barrington

372 Main Street, Great Barrington
3.7
of 5, from 111 reviews
2.0 out of 5.0

Situated in Great Barrington, this motel is within 1 mi (2 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. W.E.B. Du Bois Boyhood Homesite is 2 mi (3.2 km) away.

£45
Lantern House Motel

Lantern House Motel

256 Stockbridge Road, Great Barrington
3.9
of 5, from 41 reviews
2.5 out of 5.0

Situated in Great Barrington, this motel is within 3 mi (5 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Ski Butternut. W.E.B. Du Bois Boyhood Homesite and Mission House are also within 6 mi (10 km).

£48
Travelodge Great Barrington Berkshires

Travelodge Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington
3.1
of 5, from 86 reviews
2.0 out of 5.0

Situated in Great Barrington, this motel is within 6 mi (10 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Ski Butternut. Mission House and Berkshire Theatre Festival are also within 6 mi (10 km).

£86
Holiday Inn Express Hotel & Suites Great Barrington

Holiday Inn Express Hotel & Suites Great Barrington

415 Stockbridge Rd, Great Barrington
4.3
of 5, from 60 reviews
2.5 out of 5.0

Situated in Great Barrington, this hotel is within 6 mi (10 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Mission House. Ski Butternut and Berkshire Theatre Festival are also within 6 mi (10 km).

£45
Monument Mountain Motel

Monument Mountain Motel

247 Stockbridge Rd, Great Barrington
4.4
of 5, from 61 reviews
2.5 out of 5.0

Situated in Great Barrington, this motel is within 3 mi (5 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Ski Butternut. W.E.B. Du Bois Boyhood Homesite and Mission House are also within 6 mi (10 km).

£68
The Briarcliff Motel

The Briarcliff Motel

506 Stockbridge Road, Great Barrington
4.6
of 5, from 31 reviews
2.0 out of 5.0

Situated in Great Barrington, this motel is within 6 mi (10 km) of Mission House, Berkshire Theatre Festival, and Naumkeag. National Shrine of the Divine Mercy and Mahaiwe Performing Arts Center are also within 6 mi (10 km).

£98
The Windflower Inn

The Windflower Inn

684 South Egremont Road, Great Barrington
5.0
of 5, from 2 reviews
3.0 out of 5.0

Situated in Great Barrington, this bed & breakfast is 1.1 mi (1.8 km) from W.E.B. Du Bois Boyhood Homesite and within 6 mi (10 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. Catamount Ski Area and Ski Butternut are also within 9 mi (15 km).

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