Pittsfield Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- 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
105 East Washington Street Pittsfield IL
The price is £66 per night from 21 May to 22 May
£66
21 May - 22 May
includes taxes & fees
9.2/10 Wonderful! (356 reviews)
Enjoyable and pleasant surroundings. The quaint hotel is located on the town square with an in-house restaurant and shops and a great pizza parlor close by. Everyone was friendly and helpful.
Reviewed on 29 Apr 2026
Rodeway Inn Pittsfield
1238 W Washington St Pittsfield IL
The price is £49 per night from 31 May to 1 Jun
£49
31 May - 1 Jun
includes taxes & fees
Green Acres Hotel
625 W. Washington Pittsfield IL
Fully refundableReserve now, pay when you stay
The price is £87 per night from 17 May to 18 May
£87
17 May - 18 May
includes taxes & fees
8.6/10 Excellent! (145 reviews)
A nice, cozy, small town feel. Was recommended Gianni's pizza down the road from the hotel staff. Very friendly people, will stay again when I visit
Reviewed on 30 Apr 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Explore a world of travel with Expedia
* 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.
