Pittsfield Holidays
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- Better togetherSave up to £335 when you book a flight and hotel together*
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- Rest easyPackages with flights are ATOL protected
Your Pittsfield Holiday
Our Pittsfield holiday 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 holiday on Expedia.
Pittsfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Quincy Regional-Baldwin Field Airport (UIN) |
Population | 4,500 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Pike County Historic Museum, Old Orchard Country Club and King Park |
Top hotels in Pittsfield
William Watson Hotel
Clean room, nice staff. Helpful when needing anything. The place had a nice rustic feel to it.
Reviewed on 24 Dec 2025
Green Acres Hotel
Highly recommend. Great staff. Friendly customer service. Would stay again for sure.
Reviewed on 23 Jan 2026
Rodeway Inn
Our stay was pleasant and quiet, the only problem was that the heat was not sufficient to keep the room warm during extreme cold wave. Other than that it was fairly clean, and the staff was very friendly and helpful.
Reviewed on 30 Dec 2025
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
