Pittsfield Vacation Packages
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- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
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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.
Pittsfield Hotel Deals
William Watson Hotel
105 East Washington Street Pittsfield IL
The price is CA $110 per night from Apr 4 to Apr 5
CA $110
CA $121 total
Apr 4 - Apr 5
includes taxes & fees
Rodeway Inn Pittsfield
1238 W Washington St Pittsfield IL
The price is CA $79 per night from Apr 16 to Apr 17
CA $79
CA $87 total
Apr 16 - Apr 17
includes taxes & fees
Green Acres Hotel
625 W. Washington Pittsfield IL
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Apr 19 to Apr 20
CA $177
CA $195 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (143 reviews)
Good place to stay!
Reviewed on Feb 27, 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.
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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.
