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Pittsfield Vacation Packages

Whether you want to go away for a couple of days or a few weeks, Pittsfield is an ideal destination.

Packages in Pittsfield

Expedia deals make you save! We will make it easier for you to book the right hotel and flight combination. Experience even more while in Pittsfield with the extra money.

You can save up to 17% when you book a Pittsfield package deal.

With our international database of some 400 partner airlines and 321,000 hotels, how can you ever go wrong?

Your The Berkshires vacation will seem that much sweeter with Expedia's competitive prices.

Almost all reservations can be changed without any additional fees from us.

Pittsfield Vacation Packages

Guests in this area of The Berkshires will be sharing space with about 45,000 residents.

You'll find this destination approximately 110 miles from Boston, the state capital of Massachusetts. It is also about 7 miles from Lenox.

Looking for somewhere to spend the day with the kids? One of the most fun-filled family activities around town is Canoe Meadows Wildlife Sanctuary.

Spend a day or two exploring some of the varied exhibition spaces in the area. The Arrowhead Museum and the Berkshire Athenaeum offer a range of collections that are bound to keep you captivated. Equally rewarding are the Berkshire Museum and the Crane Museum of Papermaking.

Learn more about the past at Hancock Shaker Village and Herman Melville's Arrowhead, just a sample of the important heritage sites in and around the region.

Round up some friends and see local and touring artists performing live at the Colonial Theater or Barrington Stage Company.

When the temperature starts to drop, you'll see the locals making the trip up for a day of wintersport action at Bousquet Ski Area.

Accommodation in Pittsfield

Before you head off, make a reservation for one of the 21 Pittsfield hotels or motels found on Expedia's hotel website.

Pittsfield accommodation options include the Birchwood Inn and Hampton Inn & Suites Berkshires Lenox.


Top Hotel Deals

See all 166 Hotels in Pittsfield
£112
Hotel On North

Hotel On North

297 North Street, Pittsfield
4.8
of 5, from 129 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.

£65
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
3.6
of 5, from 449 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 miles (5 km).

£58
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield
4.1
of 5, from 440 reviews
3.0 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 miles (10 km).

£94
Hilton Garden Inn Lenox/Pittsfield

Hilton Garden Inn Lenox/Pittsfield

1032 South Street, Pittsfield
4.7
of 5, from 96 reviews
3.5 out of 5.0

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

£125
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield
3.0 out of 5.0

Situated in Pittsfield, this lodge is 1 mi (1.7 km) from Bousquet Ski Area and within 3 miles (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and Berkshire Museum are also within 3 miles (5 km).

£42
Berkshire Inn

Berkshire Inn

150 W Housatonic St, Pittsfield
3.5
of 5, from 145 reviews
2.5 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 miles (3 km).

£43
Econo Lodge

Econo Lodge

16 Cheshire Road, Pittsfield
2.7
of 5, from 234 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 miles (10 km) of Berkshire Athenaeum and Colonial Theater. Berkshire Museum and Canoe Meadows Wildlife Sanctuary are also within 6 miles (10 km).

£63
Yankee Suites Extended Stay

Yankee Suites Extended Stay

20 W Housatonic St., Pittsfield
4.4
of 5, from 78 reviews
4.5 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 miles (3 km).

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