Title: Pittsfield Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d146411.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d146411.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d146411.Car-Rental-Guide) ![](https://images.trvl-media.com/place/146411/b0600e5f-dde9-43da-82f3-8f2296a554e7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pittsfield Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Old-Orchard-Country-Club-Pittsfield.d553248621564478943.Vacation-Attraction), [John Greene Shastid House](https://www.expedia.ca/John-Greene-Shastid-House-Pittsfield.d553248621532649042.Vacation-Attraction) and [Pike County Historic Museum](https://www.expedia.ca/Pike-County-Historic-Museum-Pittsfield.d553248621564478949.Vacation-Attraction). A couple of quick clicks is all it takes to craft a tailor-made Pittsfield vacation on Expedia. ## Ready to book your vacation to Pittsfield? Choose your dates ## Pittsfield Hotel Deals ![William Watson Hotel](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### William Watson Hotel 105 East Washington Street Pittsfield IL CA $115 CA $127 total Jan 22 - Jan 23 includes taxes & fees 9.2/10 Wonderful! (254 reviews) Clean room, nice staff. Helpful when needing anything. The place had a nice rustic feel to it. Reviewed on Dec 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=6659525&PinnedHotelID=6659525&HadPinnedHotel=true®ionId=146411) ![Rodeway Inn](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/0aa674c1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rodeway Inn 1238 W Washington St Pittsfield IL Fully refundableReserve now, pay when you stay CA $83 CA $91 total Jan 21 - Jan 22 includes taxes & fees 6.6/10 (127 reviews) 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 Dec 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=5637460&PinnedHotelID=5637460&HadPinnedHotel=true®ionId=146411) ![Green Acres Hotel](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Green Acres Hotel 625 W. Washington Pittsfield IL Fully refundableReserve now, pay when you stay CA $124 CA $137 total Feb 15 - Feb 16 includes taxes & fees 8.6/10 Excellent! (141 reviews) Room climate was fine, haven't had the breakfast yet. Reviewed on Sep 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=9986625&PinnedHotelID=9986625&HadPinnedHotel=true®ionId=146411) [See all 32 properties in Pittsfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F01%2F2026&endDate=21%2F01%2F2026®ionId=146411) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app