Title: TOP 10 Hotels in Winchester, IL (from $63) 2026 - Competitive Prices | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx3000435714)[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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Winchester Pool [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-23&d2=2026-02-23&amenities=POOL) Pet-friendly [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-23&d2=2026-02-23&amenities=PETS) ## Check prices for these dates Tonight [Feb 7 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=3000435714&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 8 - Feb 9](https://www.expedia.com/Hotel-Search?regionId=3000435714&startDate=2026-02-08&endDate=2026-02-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=3000435714&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=3000435714&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![Exterior](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/1b7c7a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/6a6a12bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e4411334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites South Jacksonville [](https://www.expedia.com/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) Jacksonville 9.4/10 Exceptional (636 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexis $80 nightly $89 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/f0b06050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/aae1932a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/56f759a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Jacksonville [](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) Jacksonville 8.8/10 Excellent (503 reviews) "Clean room. Great friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence $81 nightly $93 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/df8698e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/b85b01be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/eaa23db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Jacksonville near I-72 [](https://www.expedia.com/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) Jacksonville 7.8/10 Good (444 reviews) "Staff was very friendly and room was clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim $62 nightly $69 total Feb 14 - Feb 15 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/6afc32c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/b7c49e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/23a03799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### William Watson Hotel [](https://www.expedia.com/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) Pittsfield 9.2/10 Wonderful (348 reviews) "Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Druann $82 nightly $91 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub | Soundproofing, iron/ironing board, free cribs/infant beds, Internet](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/513649eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub | Soundproofing, iron/ironing board, free cribs/infant beds, Internet](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/6afd7497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/fc256dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Jacksonville Inn [](https://www.expedia.com/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) Jacksonville 8.4/10 Very Good (753 reviews) "It was a great location and front desk staff was very friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charise $70 nightly $80 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/c2f3b0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/be2865b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/bb05caaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG [](https://www.expedia.com/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) Jacksonville 7.8/10 Good (447 reviews) "Clean room and great breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen $79 nightly $88 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![Hallway](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/946d8e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room | Premium bedding, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/1af516fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/b4ce7d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/baf4a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monroe Street Suites [](https://www.expedia.com/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) Pittsfield 9.6/10 Exceptional (58 reviews) "We had a great stay and would recommend others to stay here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brady $98 nightly $108 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/87b66cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/6dfa4459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a47c0b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/86469d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green Acres Hotel [](https://www.expedia.com/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) Pittsfield 8.6/10 Excellent (142 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeramy $107 nightly $118 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/64356a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/0778f0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/9275be3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/fff007e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa DeWolf [](https://www.expedia.com/Jacksonville-Hotels-Villa-DeWolf.h76952694.Hotel-Information) Jacksonville 10/10 Exceptional (11 reviews) "If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Catherine $239 nightly $273 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Jacksonville-Hotels-Villa-DeWolf.h76952694.Hotel-Information) ![Standard Room, 2 Queen Beds | Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/w3840h2571x0y3-b5dd01e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/61a36298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/f9ea47d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Jacksonville [](https://www.expedia.com/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) Jacksonville 8.2/10 Very Good (622 reviews) "Nice clean room, nice staff and the breakfast is great..." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mickey $55 nightly $63 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/0aa674c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/74c9995c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e6a3a05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e9aab2d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Pittsfield [](https://www.expedia.com/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) Pittsfield 6.8/10 (128 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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tod $59 nightly $65 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/d188b5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free cribs/infant beds](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/10550585.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/e9218eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, hair dryer](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/3b6ca79f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knights Inn Jacksonville East Morton Ave [](https://www.expedia.com/Springfield-Hotels-Knights-Inn-Jacksonville-East-Morton-Ave.h9309491.Hotel-Information) Jacksonville 6.8/10 (165 reviews) "The room was very clean and comfortable we only stayed one night. I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon $65 nightly $74 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Knights-Inn-Jacksonville-East-Morton-Ave.h9309491.Hotel-Information) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/aa0e636e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/8b233b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/ad02a974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Single Room, 1 King Bed, Non Smoking | Living area](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/e17bcaaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jacksonville Hotel [](https://www.expedia.com/Jacksonville-Hotels-Jacksonville-Hotel.h125256069.Hotel-Information) Jacksonville $60 nightly $67 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Jacksonville-Hotels-Jacksonville-Hotel.h125256069.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22®ionId=3000435714&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d3000435714.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d3000435714.Travel-Guide-Hotels) ## Top Winchester Hotel Reviews ![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg) ### Sleep Inn & Suites South Jacksonville 10/10 Excellent "Clean, quiet and comfortable. Have stayed many times and will continue. " [](https://expedia.com/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Green Acres Hotel](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c_y.jpg) ### Green Acres Hotel 10/10 Excellent "Highly recommend. Great staff. Friendly customer service. Would stay again for sure. " [](https://expedia.com/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.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) ### Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville 10/10 Excellent "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! " [](https://expedia.com/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 10/10 Excellent "Clean room and great breakfast." [](https://expedia.com/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![Quality Inn Jacksonville near I-72](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg) ### Quality Inn Jacksonville near I-72 10/10 Excellent "The pool was warm!! The room was nice and clean .. The water pressure in the showers along with the soap that was free was amazing .. for a cheap rate you couldn’t beat this hotel " [](https://expedia.com/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg) ### Hampton Inn Jacksonville 10/10 Excellent "Clean room. Great friendly staff. " [](https://expedia.com/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Monroe Street Suites](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/7fa649ae_y.jpg) ### Monroe Street Suites 10/10 Excellent "Great accomodations and concept for a small town. Much better than staying in a low budget chain hotel." [](https://expedia.com/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.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) ### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee. 10/10 Excellent "Kevin was an excellent host and the house on the prairie was exactly what we needed after a long day of travel. We were surprised with fresh baked cookies upon arrival.The house was very cozy and walking the trails of the prairie was great for our pup. We would definitely stay here again the future!" [](https://expedia.com/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information) ![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg) ### Best Western Jacksonville Inn 10/10 Excellent "Check-in was easy! No hassles! Room is clean and the TV works😊" [](https://expedia.com/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ## More cheap stays in Winchester ![Super 8 by Wyndham Jacksonville](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Super 8 by Wyndham Jacksonville 1003 W Morton Ave Jacksonville IL $55 nightly $63 total Mar 8 - Mar 9 Total with taxes and fees 8.2/10 Very Good! (622 reviews) [](https://expedia.com/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) ![Quality Inn Jacksonville near I-72](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn Jacksonville near I-72 200 Comfort Drive Jacksonville IL $62 nightly $69 total Feb 14 - Feb 15 Total with taxes and fees 7.6/10 Good! (444 reviews) [](https://expedia.com/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Jacksonville Inn 1709 W Morton Ave Jacksonville IL $70 nightly $80 total Feb 8 - Feb 9 Total with taxes and fees 8.4/10 Very Good! (753 reviews) [](https://expedia.com/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 2501 Holliday Lane Jacksonville IL $79 nightly $88 total Feb 22 - Feb 23 Total with taxes and fees 7.6/10 Good! (447 reviews) [](https://expedia.com/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sleep Inn & Suites South Jacksonville 2401 Holliday Ln Jacksonville IL $80 nightly $89 total Feb 15 - Feb 16 Total with taxes and fees 9.2/10 Wonderful! (633 reviews) [](https://expedia.com/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Jacksonville 1725 W Morton Ave Jacksonville IL $81 nightly $93 total Feb 15 - Feb 16 Total with taxes and fees 8.8/10 Excellent! (503 reviews) [](https://expedia.com/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ## Hotels in Winchester with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 2 properties [](https://expedia.com/4Star-Winchester-Hotels.s40-0-d3000435714.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 2 properties [](https://expedia.com/3Star-Winchester-Hotels.s30-0-d3000435714.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 15 properties [](https://expedia.com/2Star-Winchester-Hotels.s20-0-d3000435714.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Recreation:** Winchester offers a variety of outdoor activities, including scenic parks and lakes perfect for hiking and fishing. - **Family-Friendly Attractions:** Enjoy local fairgrounds and arena entertainment facilities that cater to families and children. - **Historic Sites:** Explore the historic college and university sites that add cultural depth to your visit. - **Charming Small-Town Vibe:** Experience the welcoming atmosphere and quaint shops that define Winchester. - **Convenient Accommodations:** Find a range of hotels and vacation rentals to fit any traveler's needs. ### Find great hotels near Winchester Explore a range of hotel accommodations in Winchester, Illinois, perfect for every type of traveler. Whether you're looking for pet-friendly options, family vacation experiences, or business-themed stays, Winchester has you covered. Discover the best hotels and vacation rentals, along with competitive room rates that suit your budget. Enjoy a comfortable and memorable stay in this charming town. - **[Best Western Jacksonville Inn: ](https://www.expedia.com/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information)** Nestled 12 miles from Winchester, the Best Western Jacksonville Inn is the ideal choice for pet lovers seeking a comfortable and welcoming stay. This hotel prides itself on being pet-friendly, allowing furry companions to join in on the vacation fun. With amenities such as a pet policy that includes Service Animal fee waivers and restrictions on certain pets, travelers can relax knowing their pets are accommodated. The hotel also features modern rooms and a friendly atmosphere, making it a great base for exploring the local area. - **[Sleep Inn & Suites: ](https://www.expedia.com/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information)** Located 13 miles away from Winchester, Sleep Inn & Suites caters to both pet owners and business travelers alike. This hotel’s business-oriented amenities include a well-equipped Business Center, ensuring that professionals can manage their work seamlessly while on the road. Pets are also welcome, with specific policies in place to ensure a comfortable stay for everyone. Guests appreciate the clean, cozy rooms and the commitment to providing a peaceful environment, making it an excellent choice for those balancing work and leisure. - **[Holiday Inn Express Hotel & Suites Jacksonville by IHG: ](https://www.expedia.com/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information)** This hotel, situated 13 miles from Winchester, is perfect for business travelers who value inclusivity and comfort. The Holiday Inn Express offers a range of business facilities, including accessible Business Center, Conference Space, and Meeting Rooms, making it an excellent choice for corporate events. Additionally, the hotel is LGBTQIA welcoming and pet-friendly, ensuring a diverse and inclusive atmosphere for all guests. With its modern amenities and commitment to service, this hotel is a top pick for travelers seeking a well-rounded experience. ### Where to stay near Winchester Winchester, Illinois, offers a charming blend of outdoor adventures and family-friendly experiences. Just a short drive from downtown, you'll find scenic landscapes perfect for weekend getaways. Enjoy the small-town vibe while exploring nearby attractions, from parks to quaint shops. With convenient vacation rentals available, Winchester is an ideal base for your adventures, whether you're hiking, fishing, or simply soaking in the beautiful surroundings. Get ready to create unforgettable memories in this delightful city. - **[Lynnville: ](https://www.expedia.com/Lynnville-Hotels.d553248634983184392.Travel-Guide-Hotels)** A charming village located 7 miles from Winchester, Lynnville offers visitors a unique glimpse into local culture and history. Despite a steady influx of travelers throughout the year, summer months from June to August see the highest number of visitors. Here, you can immerse yourself in cultural experiences while exploring local museums and historic buildings. The quaint atmosphere and friendly locals make Lynnville a perfect stop for those looking to savor small-town charm. - **[Florence: ](https://www.expedia.com/Florence-Hotels.d553248634983143770.Travel-Guide-Hotels)** Situated 8 miles from Winchester, Florence is a picturesque city known for its stunning scenery and outdoor activities. With traveler numbers remaining consistent year-round, the summer months are particularly vibrant. Visitors are drawn to Florence for its natural beauty, especially the nearby river, which provides a serene backdrop for leisurely strolls and picnics. Whether you're into fishing, kayaking, or simply enjoying the outdoors, Florence is an idyllic spot for nature enthusiasts. - **[Manchester: ](https://www.expedia.com/Manchester-Hotels.d553248634983342309.Travel-Guide-Hotels)** Just 9 miles from Winchester, Manchester is a city that thrives on adventure and outdoor family fun. With a steady stream of visitors year-round, the city is particularly lively in the summer. Manchester boasts a variety of activities ranging from campgrounds to exploring nearby state parks. History buffs will appreciate the historic buildings and sites scattered throughout the area. For families looking to enjoy the great outdoors together, Manchester is a fantastic destination filled with adventure and excitement. ### Things to do near Winchester Winchester, Illinois, is perfect for an outdoor family vacation with plenty of entertainment options. Visitors can enjoy a variety of activities, including a recreational area, an arena entertainment facility, and local theaters. With its inviting outdoor attractions and engaging city experiences, Winchester promises a delightful getaway for families seeking fun and relaxation. **Shopping** In Winchester, you can enjoy local shops offering unique gifts and souvenirs. If you're up for a drive, head to the Jacksonville Mall, about 15 miles away, where you'll find a variety of retail stores and dining options for a complete shopping experience. **Recreation** Experience the energetic vibes at [Future Champions Sport Complex](https://www.expedia.com/Future-Champions-Sport-Complex-Hotels.0-l835797978406019072-0.Travel-Guide-Filter-Hotels), where you can engage in various sports activities. For a serene escape, visit [Jacksonville Community Park](https://www.expedia.com/Jacksonville-Community-Park-Hotels.0-l835650478598635520-0.Travel-Guide-Filter-Hotels), perfect for relaxation and wellness. Finally, enjoy a round of golf at [Old Orchard Country Club](https://www.expedia.com/Old-Orchard-Country-Club-Hotels.0-l553248621564478943-0.Travel-Guide-Filter-Hotels), surrounded by beautiful outdoor scenery. **Adventure** In Winchester, explore the scenic trails of the nearby Jim Edgar Panther Creek State Fish and Wildlife Area, perfect for hiking and wildlife spotting. For a thrilling experience, try your hand at fishing or boating on the beautiful lakes, where adventure meets tranquility in nature. **Nightlife** In Winchester, the Small Eli Ferris Wheel, located 14 miles away, offers a fun-filled amusement ride experience. While nightlife options may be limited, you can enjoy local diners and bars that provide a cozy atmosphere for unwinding after a day of exploration. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Winchester To save money on your trip to Winchester, consider visiting during the cheaper months of January to February and November, with Tuesdays offering the lowest hotel prices. Use Expedia's search tool to find affordable accommodations by sorting results from lowest to highest price and filtering by hotel type, such as eco-certified options. Booking a package that combines flights, hotels, and activities can also yield savings. Don’t forget to join Expedia's One Key membership for exclusive discounts and to earn OneKeyCash for future bookings. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are January to February and November, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Friday. - **Find cheap hotels on Expedia:** Expedia’s search tool makes it easy for you to set your budget and choose your desired location, among other preferences. You can arrange the results to display prices from lowest to highest, ensuring you find the most affordable hotels right away. Additionally, you can refine your search by hotel type. For instance, if you select the Eco-certified filter, you’ll discover sustainable and environmentally-friendly hotels available for booking. - **Consider bundling your trip:** You can save money by combining your Winchester hotel reservation with your flights and activities when you book an Expedia package. - **Become a One Key member:** Join [Expedia's One Key membership](https://www.expedia.com/welcome-one-key) program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels. ### Find the best attractions near Winchester Winchester, Illinois, offers a delightful vacation experience perfect for families and outdoor enthusiasts. Visitors can explore a variety of attractions, including the local fairground, historic college and university sites, and scenic lakes. Whether you're looking for outdoor adventures, cultural experiences, or a relaxing beach vibe, Winchester has something to satisfy every traveler’s interests. - **[Morgan County Fairgrounds: ](https://www.expedia.com/Morgan-County-Fairgrounds-Hotels.0-l553248621560054950-0.Travel-Guide-Filter-Hotels)** Experience the lively atmosphere of Morgan County Fairgrounds, a vibrant space perfect for family-friendly events. Enjoy the outdoor activities and engage with local culture during fairs and community gatherings held throughout the year. - **[Illinois College: ](https://www.expedia.com/Illinois-College-Hotels.0-l553248621560054952-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the rich history and culture at Illinois College, a beautiful campus with stunning architecture. Take a stroll through the grounds, explore its historical significance, and appreciate the academic spirit that permeates this historic institution. - **[Lake Jacksonville: ](https://www.expedia.com/Lake-Jacksonville-Hotels.0-l6124325-0.Travel-Guide-Filter-Hotels)** Discover the serene beauty of Lake Jacksonville, an ideal spot for outdoor enthusiasts and couples seeking romance. Enjoy beach activities, picturesque scenery, and peaceful moments by the water, making it a perfect getaway. ### Best time to go to Winchester The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 28.4°F (-2.0°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 31.3°F (-0.4°C) | Light Rain | Mostly Cloudy | Moderately Low | Slightly Low | | March | 43.9°F (6.6°C) | Light Rain | Mostly Sunny | Average | Average | | April | 53.8°F (12.1°C) | Light Rain | Mostly Sunny | Average | Average | | May | 64.4°F (18.0°C) | Light Rain | Mostly Sunny | Average | Average | | June | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | July | 76.1°F (24.5°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | August | 74.7°F (23.7°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly High | | September | 68.9°F (20.5°C) | Light Rain | Mostly Sunny | Moderately High | Average | | October | 56.5°F (13.6°C) | Light Rain | Mostly Sunny | Average | Average | | November | 43.7°F (6.5°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | December | 34.5°F (1.4°C) | Light Rain | Mostly Sunny | Average | Average | ### The nearest major airports for your trip to Winchester Traveling to Winchester, Illinois, is convenient with several nearby airports. St. Louis Lambert International Airport ([STL](https://www.expedia.com/Lambert-St-Louis-Intl-Airport-Hotels.0-aSTL-0.Travel-Guide-Filter-Hotels)) is located 62 miles away, with nearby hotels like [The Ritz-Carlton](https://www.expedia.com/St-Louis-Hotels-The-Ritz-Carlton.h6132.Hotel-Information) (7 miles) and [Ameristar Casino Resort and Spa](https://www.expedia.com/St-Louis-Hotels-Ameristar-Casino-Resort-And-Spa.h1873292.Hotel-Information) (7 miles), offering various transportation services. Springfield's Abraham Lincoln Capital Airport ([SPI](https://www.expedia.com/Abraham-Lincoln-Capital-Airport-Hotels.0-aSPI-0.Travel-Guide-Filter-Hotels)), situated 44 miles from Winchester, features the [President Abraham Lincoln Springfield - DoubleTree by Hilton](https://www.expedia.com/Springfield-Hotels-President-Abraham-Lincoln-Springfield-A-DoubleTree-By-Hilton.h5491.Hotel-Information) (3 miles) and Crowne Plaza Springfield (7 miles), both providing shuttle services. Quincy Regional-Baldwin Field ([UIN](https://www.expedia.com/Quincy-Regional-Baldwin-Field-Airport-Hotels.0-aUIN-0.Travel-Guide-Filter-Hotels)) is also 44 miles away, with options like Holiday Inn Quincy East (8 miles) and [Town & Country Inn and Suites](https://www.expedia.com/Quincy-Hotels-Town-Country-Inn-And-Suites.h1562708.Hotel-Information) (7 miles), offering easy access to the airport. ## Frequently asked questions ### What is the best area to stay in Winchester? > Winchester's downtown is the heart of the community, featuring a classic American town square surrounded by local businesses. You'll find a few small shops, eateries, and historic buildings here, offering a glimpse into local life. The area is easily walkable and serves as a convenient base for exploring the town and nearby attractions. > > > For travelers looking for a quiet and authentic experience, staying near the town square is ideal. ### When is the best time to go to Winchester? > Late spring provides comfortable temperatures, typically ranging from the 60s to high 70s Fahrenheit, with blooming flora. This is a great time for couples to enjoy scenic drives through the countryside or visit local parks without the summer crowds. > > > Early fall brings cooler, crisp air and the beautiful changing colors of the leaves, with temperatures generally in the 50s to low 70s Fahrenheit. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? > \*Excludes taxes and fees. 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