Title: Visit Winchester: 2026 Travel Guide for Winchester, Illinois | Expedia.com [Hotels in Winchester](https://expedia.com/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d3000435714.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d3000435714.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d3000435714.Destination-Travel-Guides) # Winchester, IL ## Travel Guide ## Visit Winchester ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_3000435714) - Winchester Hotel Deals - Vacation Rentals in Winchester ![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sleep Inn & Suites South Jacksonville 2401 Holliday Ln Jacksonville IL $82 nightly $91 total Mar 22 - Mar 23 Total with taxes and fees Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 9.4/10 Exceptional! (645 reviews) Clean rooms, kind staff, good breakfast and my dog stayed at a reasonable rate. Many thanks! Reviewed on Feb 22, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=23831866&PinnedHotelID=23831866&HadPinnedHotel=true®ionId=3000435714) ![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Jacksonville Inn 1709 W Morton Ave Jacksonville IL $70 nightly $80 total Mar 5 - Mar 6 Total with taxes and fees Stay at this hotel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ... 8.4/10 Very Good! (760 reviews) Best place in Jacksonville Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=124218&PinnedHotelID=124218&HadPinnedHotel=true®ionId=3000435714) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 2501 Holliday Lane Jacksonville IL $90 nightly $100 total Mar 8 - Mar 9 Total with taxes and fees Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Prairie Land Heritage Museam ... [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=1793078&PinnedHotelID=1793078&HadPinnedHotel=true®ionId=3000435714) [See all 42 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F5%2F2026&endDate=3%2F6%2F2026®ionId=3000435714) 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. ![Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL ](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428476/w906h683x60y0-f10f078b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL Jacksonville IL Stay at this cabin in Jacksonville. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Lake Jacksonville and Prairie Land Heritage ... 10/10 Exceptional! (16 reviews) The house was very quaint and cozy. Stocked materials for coffee and a water filter pitcher for the tap water. Place was very clean and welcoming after driving for half the day. Reviewed on Feb 15, 2026 [](https://expedia.com/Jacksonville-Hotels-Bunkhouse-Seventy-Four.h103428476.Hotel-Information) ![Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville ](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w449h683x287y0-7464266c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville Jacksonville IL Stay at this cabin in Jacksonville. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Lake Jacksonville and Prairie Land Heritage ... 10/10 Exceptional! (9 reviews) If you love the country life, or have lived in the country for awhile, this place will bring you right back to it. Absolutely amazing, in all ways. Will be back again. Thank you! Reviewed on Jan 21, 2026 [](https://expedia.com/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information) ![Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee. Murrayville IL Stay at this vacation home in Murrayville. Enjoy free WiFi, a garden, and laundry facilities. Popular attraction Lake Jacksonville is located nearby. 9.8/10 Exceptional! (62 reviews) Stayed twice on a recent trip south and back from our home in WI. Dogs absolutely loved the property. Kevin is extremely welcoming, fresh cookies warm from the oven were a treat. Bed is very comfortable. We've always stayed at a place off of the I in past trips, this was so much more peaceful, and ... Reviewed on Mar 1, 2026 [](https://expedia.com/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information) [See all properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=3000435714&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=2026-03-04&endDate=2026-03-05)[Mar 4 - Mar 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=2026-03-04&endDate=2026-03-05) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=2026-03-05&endDate=2026-03-06)[Mar 5 - Mar 6](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=2026-03-05&endDate=2026-03-06) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=3%2F6%2F2026&endDate=3%2F8%2F2026)[Mar 6 - Mar 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=3%2F6%2F2026&endDate=3%2F8%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=3000435714&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026) ## Cities near Winchester ![Court House in Pittsfield](https://images.trvl-media.com/place/146411/e1162892-98db-4e1f-aa10-c1e92fa5be83.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Pittsfield ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Alsey Hotels ](https://www.expedia.com/Alsey-Hotels.d3000346086.Travel-Guide-Hotels) - [Apartments in Alsey ](https://www.expedia.com/Alsey-Apartments.d3000346086-aaApartments.Travel-Guide-Accommodation) - [Lynnville Hotels ](https://www.expedia.com/Lynnville-Hotels.d553248634983184392.Travel-Guide-Hotels) - [Florence Hotels ](https://www.expedia.com/Florence-Hotels.d553248634983143770.Travel-Guide-Hotels) - [Manchester Hotels ](https://www.expedia.com/Manchester-Hotels.d553248634983342309.Travel-Guide-Hotels) - [Vacation Homes in Bluffs ](https://www.expedia.com/Bluffs-Private-Vacation-Homes.d553248634983410026-aaPrivateVacationHomes.Travel-Guide-Accommodation) - 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[Car rentals near Time ](https://www.expedia.com/Car-Rentals-In-Time.d553248634983120929.Car-Rental-Guide) - [Car rental Jacksonville Airport (IJX) ](https://www.expedia.com/Car-Rentals-In-Jacksonville-Municipal.d5786185.Car-Rental-Guide) - [Jacksonville Vacation Rentals ](https://www.expedia.com/Jacksonville-Vacation-Rentals.d7884.Travel-Guide-VacationRentals) - Cities near Winchester - Places of interest [Jacksonville](https://expedia.com/Jacksonville.dx7884)[Pittsfield](https://expedia.com/Pittsfield.dx146411)[Alsey](https://expedia.com/Alsey.dx3000346086)[Roodhouse](https://expedia.com/Roodhouse.dx3000346545) - [Mississippi River ](https://expedia.com/Mississippi-River-United-States-of-America.d6209928.Vacation-Attraction) - [Future Champions Sport Complex ](https://expedia.com/Future-Champions-Sport-Complex-Jacksonville.d835797978406019072.Vacation-Attraction) - [Illinois College ](https://expedia.com/Illinois-College-Jacksonville.d553248621560054952.Vacation-Attraction) - [Lake Jacksonville ](https://expedia.com/Lake-Jacksonville-Jacksonville.d6124325.Vacation-Attraction) - [Old Orchard Country Club ](https://expedia.com/Old-Orchard-Country-Club-Pittsfield.d553248621564478943.Vacation-Attraction) - [Jacksonville Community Park ](https://expedia.com/Jacksonville-Community-Park-Jacksonville.d835650478598635520.Vacation-Attraction) - [John Greene Shastid House ](https://expedia.com/John-Greene-Shastid-House-Pittsfield.d553248621532649042.Vacation-Attraction) - [Pike County Historic Museum ](https://expedia.com/Pike-County-Historic-Museum-Pittsfield.d553248621564478949.Vacation-Attraction) - [Woodlawn Farm ](https://expedia.com/Woodlawn-Farm-Jacksonville.d835646551595532288.Vacation-Attraction) - [King Park ](https://expedia.com/King-Park-Pittsfield.d553248621564478944.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels 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. 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