Pittsfield Vacation Packages
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Your Pittsfield Vacation
When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theater and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like.
Pittsfield Hotel Deals
Berkshire Mountain Lodge
We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being ...
Reviewed on Feb 1, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
generally good
Reviewed on Jan 19, 2026
Best Western Plus Berkshire Hills Inn & Suites
Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great.
Reviewed on Jan 20, 2026
Discover the most popular places to visit in Pittsfield
Hancock Shaker Village
You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.
Canoe Meadows Wildlife Sanctuary
You can take time to visit Canoe Meadows Wildlife Sanctuary during your travels to Pittsfield. Wander the lakeside in this quaint area.
