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Pittsfield Vacation Packages
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
Crowne Plaza Pittsfield-Berkshires
1 West St, PittsfieldLocated 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).
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, PittsfieldLocated 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).
Yankee Suites Extended Stay
20 W Housatonic St., PittsfieldSituated 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).
Hilton Garden Inn Lenox/Pittsfield
1032 South Street, PittsfieldSituated 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).
Heart of the Berkshires Motel
970 W Housatonic St, PittsfieldSituated 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.
Berkshire Inn
150 W Housatonic St, PittsfieldLocated 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).
Hotel On North
297 North Street, PittsfieldSituated 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.
Econo Lodge
16 Cheshire Road, PittsfieldSituated 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).
Top Flight + Hotel Deals
Comfort Inn & Suites East Greenbush - Albany
2.5 out of 5.0Tue, 14 Nov - Sat, 18 Nov
London City - Albany Intl.
£741
per person
The Century House, an Ascend Hotel Collection Member
3.0 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£628
per person
Radisson Hotel Albany
3.0 out of 5.0Thu, 9 Nov - Mon, 13 Nov
London City - Albany Intl.
£621
per person
La Quinta Inn & Suites Latham Albany Airport
2.5 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£612
per person
Fairfield Inn by Marriott Albany University Area
2.5 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£659
per person
Cocca's Inn & Suites Wolf Rd, Albany Airport
2.0 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£539
per person
Red Carpet Inn & Suites
2.5 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£541
per person
Golden Circle Inn
2.0 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£579
per person
Days Inn and Suites Albany
2.0 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£540
per person
Howard Johnson Inn - Albany
1.5 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£555
per person
Super 8 Schenect/Albany Area
2.0 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£567
per person
Days Inn Albany SUNY
2.0 out of 5.0Wed, 1 Nov - Wed, 8 Nov
Manchester - Albany Intl.
£566
per person
Top Deals on Flights
These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.
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