
Pittsfield Vacations from $982
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Your Pittsfield Vacation
Our Pittsfield vacation packages give you endless opportunities to enjoy new sights, sounds and tastes. And with all the planning taken care of, you can breathe easy and enjoy your city adventure without a worry in the world. Every trip to Pittsfield needs a well-thought-out itinerary. Fill yours with leading attractions like Old Orchard Country Club, John Greene Shastid House and Pike County Historic Museum. A couple of quick clicks is all it takes to craft a tailor-made Pittsfield vacation on Expedia.
The Latest Pittsfield vacation packages

Discover the most popular places to visit in Pittsfield
Old Orchard Country Club
Enjoy a round of golf in Pittsfield at Old Orchard Country Club. Experience the area's entertainment venues and theater scene.
Pike County Historic Museum
You can study the exhibits at Pike County Historic Museum, a museum with a story of its own, during your travels to Pittsfield. Experience the area's entertainment venues and theater scene.
King Park
Explore the great outdoors at King Park, a lovely green space in Pittsfield. Experience the area's entertainment venues and theater scene.
Pittsfield Hotel Deals

William Watson Hotel
Reviewed on Aug 6, 2025

Rodeway Inn
Reviewed on Jul 7, 2025

Green Acres Hotel
Reviewed on Jul 23, 2025