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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 135 Hotels in The Berkshires
$135
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
4.2
of 5, from 768 reviews
0.0 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).

$129
Cranwell Spa and Golf Resort

Cranwell Spa and Golf Resort

55 Lee Road, Lenox
4.1
of 5, from 97 reviews
4.0 out of 5.0

Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company and Wood's Pond are also within 3 mi (5 km).

$118
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 214 reviews
3.0 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.

$84
Days Inn Great Barrington

Days Inn Great Barrington

372 Main Street, Great Barrington
3.8
of 5, from 383 reviews
2.5 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.

$88
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
3.6
of 5, from 442 reviews
4.0 out of 5.0

Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary and Arrowhead Museum are also within 3 mi (5 km).

$99
Holiday Inn Berkshires

Holiday Inn Berkshires

40 Main St, North Adams
4.1
of 5, from 441 reviews
3.5 out of 5.0

Located in the heart of North Adams, this hotel is within a 10-minute walk of Mass MoCA, North Adams Public Library, and Western Gateway Heritage State Park. Windsor Lake Park and Natural Bridge State Park are also within 2 mi (3 km).

$110
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
4.6
of 5, from 33 reviews
3.5 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).

$101
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
4.6
of 5, from 346 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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