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The Berkshires Vacation Packages

This mountain range in west Massachusetts combines spectacular nature, world-class cultural destinations and charming New England towns. 

The Berkshires is a picturesque mountain range that runs for 98 miles (158 kilometers) along Massachusetts west border. Known for its scenic beauty and its cultural offerings, the Berkshires is one of the state’s top vacation destinations.

Bring a pair of comfortable hiking boots and explore the beautiful wilderness. Hike some of the famous Appalachian Trail, which runs through the Berkshires on its 2,160-mile (3,476.18-kilometer) journey. The Berkshires portion of the trail passes through spectacular peaks such as Mount Greylock and Mount Everett, along with small New England towns.

Explore the trees at the “living tree library” of Hebert Arboretum. This 231-acre (93.5-hectare) park lies in the city of Pittsfield, the largest town in the Berkshires. The arboretum is home to fields, forests and wildflowers. During the spring and fall, the garden is host to migrating songbirds.

Surround yourself with flowers at the Berkshire Botanical Garden in Stockbridge, 14 miles (22.5 kilometers) south of Pittsfield. Browse more than 3,000 species of plants in the botanical garden, which is one of the oldest public gardens in the United States. It was founded in 1934. Stay in Stockbridge to visit the Norman Rockwell Museum of Art, which has the world’s largest collection of work by the famous American artist. Rockwell spent the last several decades of his life in the town, and the museum displays over 500 pieces of his art. 

If you’re in Stockbridge in summer, visit Tanglewood. The music venue is the summer home of the Boston Symphony Orchestra and hosts regular music concerts.

Drive 1-hour north of Stockbridge to North Adams for the Massachusetts Museum of Contemporary Art, one of the largest and most renowned contemporary art centers in the United States. Look through 19 galleries in the converted factory space. 

The best time to visit the Berkshires is in summer, when the Boston Symphony Orchestra is in residence and many visitors flock to the mountains from New York and Boston. Cold winters are best enjoyed indoors, but there are plenty of museums, concert halls and theaters to keep visitors occupied. 

To learn more about all there is to do in the region, visit the official Berkshires of Western Massachusetts tourism website.


Top Hotel Deals

See all 133 Hotels in The Berkshires
£76
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
4.1
of 5, from 238 reviews
3.0 out of 5.0

Situated in Hancock, this condo is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 km) of Waubeeka Golf Links and New Lebanon Library. Mount Lebanon Shaker Village and Berkshire Athenaeum are also within 12 mi (20 km).

Rose and Goat Retreat

Rose and Goat Retreat

9 Moores Rd, North Adams
4.0 out of 5.0

Located in the mountains, this family-friendly resort is within 9 mi (15 km) of Windsor Lake Park, Natural Bridge State Park, and Mass MoCA. North Adams Public Library and Western Gateway Heritage State Park are also within 9 mi (15 km).

1896 House Brookside & Pondside Country Motels

1896 House Brookside & Pondside Country Motels

910 Cold Spring Rd, Williamstown
4.2
of 5, from 10 reviews
0.0 out of 5.0

Situated in a rural location, this bed & breakfast is within 3 mi (5 km) of Williamstown Historical Museum, 62 Center for Theater and Dance, and Chapin Library of Rare Books and Manuscripts. Williams College Museum of Art and Williams College are also within 3 mi (5 km).

£87
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock
3.8
of 5, from 145 reviews
3.0 out of 5.0

Located in the mountains, this Hancock condominium resort offering ski-in/ski-out access is 6.1 mi (9.8 km) from Mount Greylock State Reservation Visitor Center and within 16 mi (25 km) of Waubeeka Golf Links and Canoe Meadows Wildlife Sanctuary. New Lebanon Library and Mount Lebanon Shaker Village are also within 12 mi (20 km).

£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.

£86
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
4.7
of 5, from 15 reviews
3.0 out of 5.0

Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 3 mi (5 km).

£51
Super 8 Lee/Berkshires/Outlet Area

Super 8 Lee/Berkshires/Outlet Area

170 Housatonic Street, Lee
3.5
of 5, from 74 reviews
2.0 out of 5.0

Situated in Lee, this motel is within a 15-minute walk of Lee Prime Outlets, Lee Library, and Animagic Museum of Animation. Greenock Country Club is 0.9 mi (1.4 km) away.

£76
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
4.6
of 5, from 113 reviews
2.5 out of 5.0

Situated in a rural location, this hotel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary and Canoe Meadows Wildlife Sanctuary are also within 3 mi (5 km).

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