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Pittsfield Vacation Packages

Located at a fork in the Housatonic River, this city provides an appealing mix of cultural diversions and outdoor pursuits. 

The largest town in the Berkshires region, Pittsfield has varied shops, services and restaurants, making it a great jumping-off point for hiking and camping trips to the nearby Pittsfield State Forest. There is much to explore within Pittsfield itself. Check out colorful street art, discover museum exhibits and attend performances in one of its cultural venues.

Pittsfield was settled in the mid-18th century after a wealthy Bostonian purchased the land as a speculative investment. The village slowly grew in size during the 1800s and 1900s as wool and electrical manufacturing industries flourished. Get a taste of local history at the Berkshire Museum, one of the main tourist draws. A small museum with eclectic exhibits focusing on art, history and nature, it also has an interactive aquarium and hands-on activities for kids to enjoy. 

In downtown Pittsfield, enjoy Artscape, a self-guided walking tour of the city’s street art. Take a guided tour of Herman Melville's Arrowhead, the lovingly maintained former residence of Herman Melville, who wrote his famous novel Moby Dick here in Pittsfield.

In the evenings enjoy culture with a classical or contemporary professional ballet performance at the Albany Berkshire Ballet. Investigate the Colonial Theater, a gilded old theater that has been fully restored and offers an entertaining program including music and theatrical performances. The Pittsfield Visitors Center is found in the theater’s lobby.  

In summer, make a splash at the area’s numerous lakes, which have plentiful opportunities for swimming, fishing and boating. As well as hiking through the forest, find year-round recreation available at the Bousquet Ski Resort and Family Fun Center. Stop at the complex outside of ski season to enjoy the water park and go-karting track, perfect for summer fun.

Drive to Pittsfield or use Amtrak's Lakeshore Limited rail service, which operates daily between Boston and Chicago. Pittsfield is also served by intercity bus lines from Boston, New York and Albany.


Top Hotel Deals

See all 135 Hotels in Pittsfield
£68
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
3.5
of 5, from 129 reviews
3.5 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).

£69
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield
4.1
of 5, from 131 reviews
2.5 out of 5.0

Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from Bousquet Ski Area. Colonial Theater and Berkshire Museum are also within 6 mi (10 km).

£65
Yankee Suites Extended Stay

Yankee Suites Extended Stay

20 W Housatonic St., Pittsfield
4.1
of 5, from 22 reviews
4.0 out of 5.0

Situated in Pittsfield, this guesthouse is within a 5-minute walk of Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe Meadows Wildlife Sanctuary are also within 2 mi (3 km).

£88
Hilton Garden Inn Lenox/Pittsfield

Hilton Garden Inn Lenox/Pittsfield

1032 South Street, Pittsfield
4.6
of 5, from 22 reviews
3.0 out of 5.0

Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and Berkshire Museum are also within 3 mi (5 km).

£48
Heart of the Berkshires Motel

Heart of the Berkshires Motel

970 W Housatonic St, Pittsfield
2.6
of 5, from 19 reviews
2.0 out of 5.0

Situated in Pittsfield, this motel is within 3 mi (5 km) of Hancock Shaker Village, Colonial Theater, and Berkshire Museum. Berkshire Athenaeum is 2.8 mi (4.4 km) away.

£56
Berkshire Inn

Berkshire Inn

150 W Housatonic St, Pittsfield
3.6
of 5, from 50 reviews
2.0 out of 5.0

Located in the heart of Pittsfield, this motel is within a 15-minute walk of Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe Meadows Wildlife Sanctuary are also within 2 mi (3 km).

£115
Hotel On North

Hotel On North

297 North Street, Pittsfield
4.7
of 5, from 23 reviews
3.5 out of 5.0

Situated in Pittsfield, this hotel is within a 10-minute walk of Berkshire Museum, Berkshire Athenaeum, and Colonial Theater. Canoe Meadows Wildlife Sanctuary is 2.1 mi (3.3 km) away.

£58
Econo Lodge

Econo Lodge

16 Cheshire Road, Pittsfield
2.5
of 5, from 60 reviews
1.5 out of 5.0

Situated in the suburbs, this motel is 1.6 mi (2.6 km) from Crane Museum of Papermaking and within 6 mi (10 km) of Berkshire Athenaeum and Colonial Theater. Berkshire Museum and Canoe Meadows Wildlife Sanctuary are also within 6 mi (10 km).

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