Title: Book The Best Hotels in Winchester, IL for 2026 from CA $86 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000435714.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/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__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-27&d2=2026-03-27&amenities=POOL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-27&d2=2026-03-27&travelerType=family_friendly) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-27&d2=2026-03-27&amenities=PETS) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America®ionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-27&d2=2026-03-27&lodging=CABIN) ## Check prices for these dates Tonight [Mar 11 - Mar 12](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-03-11&endDate=2026-03-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 12 - Mar 13](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-03-12&endDate=2026-03-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-03-20&endDate=2026-03-22&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) ![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) ![Lobby](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/1b7c7a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/c41d8356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites South Jacksonville [](https://www.expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) Jacksonville 9.4/10 Exceptional (646 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexis CA $117 CA $130 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.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/eaa23db4.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) ### Quality Inn Jacksonville near I-72 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) Jacksonville 7.8/10 Good (447 reviews) "Staff was very friendly and room was clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim CA $91 CA $101 total includes taxes & fees Apr 9 - Apr 10 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn.h474237.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/56f759a8.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) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/f0b06050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Jacksonville [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) Jacksonville 8.8/10 Excellent (508 reviews) "Great property, great staff, comfy beds" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Ann CA $110 CA $126 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.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/7000000/6660000/6659600/6659525/080807c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Ensuite (King Suite)](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/80a90a0a.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) ### William Watson Hotel [](https://www.expedia.ca/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 CA $106 CA $117 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/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](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](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/6afd7497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/1baf1987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Jacksonville Inn [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) Jacksonville 8.4/10 Very good (761 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 CA $81 CA $93 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/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/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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/c2f3b0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG [](https://www.expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) Jacksonville 7.8/10 Good (450 reviews) "Clean room and great breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $121 CA $134 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/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) ![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) ![Comfort Room](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) ### Monroe Street Suites [](https://www.expedia.ca/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 CA $133 CA $146 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/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) ![Interior](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/86469d30.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) ### Green Acres Hotel [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) Pittsfield 8.6/10 Excellent (143 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeramy CA $158 CA $173 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.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/e9aab2d4.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](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e6a3a05e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) Pittsfield 6.8/10 (129 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 CA $70 CA $78 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/w3840h2571x0y3-b5dd01e1.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) ![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) ![Business centre](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/69b3d11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Jacksonville [](https://www.expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) Jacksonville 8.2/10 Very good (625 reviews) "Nice clean room, nice staff and the breakfast is great..." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mickey CA $75 CA $86 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.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) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/f0ad4448.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) ![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) ### Knights Inn Jacksonville East Morton Ave [](https://www.expedia.ca/Springfield-Hotels-Knights-Inn-Jacksonville-East-Morton-Ave.h9309491.Hotel-Information) Jacksonville 6.8/10 (166 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 CA $88 CA $101 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/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) ![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) ![Exterior](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/8b233b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/209ee9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jacksonville Inn & Suites [](https://www.expedia.ca/Jacksonville-Hotels-Jacksonville-Hotel.h125256069.Hotel-Information) Jacksonville 6.0/10 (2 reviews) "TV didn’t work properly. Bathtub dripped all night long. No hot water for shower. No complimentary breakfast served as advertised. Very dissatisfied with stay and refused refund by management. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marvin CA $102 CA $114 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26®ionId=3000435714&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/deals?rfrr=HTG_SPRING_PROMO_3000435714) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d3000435714.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d3000435714.Travel-Guide-Hotels) ## Top Winchester Hotel Reviews ## Recent Reviews in Winchester ![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 2/10 Terrible "I will not be staying at this property again and I will 100% be back in this area. My room smelt of animal urine. My comforter had a large yellow stain on it that had a remnant urine smell. I switched it out for a different blanket. Luckily running the air conditioning a little helped to cycle the urine smell out of the room. " [](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg) ### Best Western Jacksonville Inn 8/10 Good "Inexpensive, clean friendly place to sleep." [](https://expedia.ca/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) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 8/10 Good "A swimming pool is advertised but has not been working for 4 years straight " [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg) ### Hampton Inn Jacksonville 4/10 Poor "Needs an upgrade. Rooms look old and very dated" [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Jacksonville Inn & Suites](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/aa0e636e_y.jpg) ### Jacksonville Inn & Suites 2/10 Terrible "TV didn’t work properly. Bathtub dripped all night long. No hot water for shower. No complimentary breakfast served as advertised. Very dissatisfied with stay and refused refund by management. " [](https://expedia.ca/Jacksonville-Hotels-Jacksonville-Hotel.h125256069.Hotel-Information) ![Green Acres Hotel](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/87b66cdb_y.jpg) ### Green Acres Hotel 10/10 Excellent "Good place to stay!" [](https://expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Super 8 by Wyndham Jacksonville](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/w3840h2571x0y3-b5dd01e1_y.jpg) ### Super 8 by Wyndham Jacksonville 4/10 Poor "Upon arrival girl at front desk we were first given a 2nd floor room. Asked where the elevator was and was told that they didn't have one Asked for main level which they had. I then asked where they kept the luggage cart. She wheeled out laundry basket on wheels. Then getting into bed and hear a water leak in the bathroom Water leaking through the ceiling above the tub By the appearance of the ceiling tiles it has been a issue for quite some time. Breakfast of okay but not a lot of selection. " [](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) ![Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo](https://images.trvl-media.com/lodging/114000000/113140000/113134000/113133953/2808cbb6_y.jpg) ### Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo 10/10 Excellent "Had a great stay. Place is in nice location. Very fast on replying to questions. Thank you " [](https://expedia.ca/Kampsville-Hotels-Charming-4-Bedroom-Sleeps-10-Lodge-With-AC-And-WiFi-In-Welcoming-Nebo.h113133953.Hotel-Information) ![Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville ](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w1021h680x0y0-e4ca8d16_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.ca/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information) ## More cheap stays in Winchester ![Super 8 by Wyndham Jacksonville](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/w3840h2571x0y3-b5dd01e1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Super 8 by Wyndham Jacksonville 1003 W Morton Ave Jacksonville IL CA $75 CA $86 total Apr 2 - Apr 3 includes taxes & fees 8.2/10 Very Good! (625 reviews) [](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.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 CA $81 CA $93 total Mar 12 - Mar 13 includes taxes & fees 8.4/10 Very Good! (761 reviews) [](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.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 CA $91 CA $101 total Apr 9 - Apr 10 includes taxes & fees 7.8/10 Good! (447 reviews) [](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Jacksonville Inn & Suites](https://images.trvl-media.com/lodging/126000000/125260000/125256100/125256069/aa0e636e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Jacksonville Inn & Suites 1914 Southbrooke Rd Jacksonville IL CA $102 CA $114 total Mar 12 - Mar 13 includes taxes & fees 6/10 (2 reviews) [](https://expedia.ca/Jacksonville-Hotels-Jacksonville-Hotel.h125256069.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 CA $110 CA $126 total Mar 19 - Mar 20 includes taxes & fees 8.8/10 Excellent! (508 reviews) [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.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 CA $121 CA $134 total Mar 15 - Mar 16 includes taxes & fees 7.8/10 Good! (450 reviews) [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.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.ca/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.ca/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.ca/2Star-Winchester-Hotels.s20-0-d3000435714.Travel-Guide-Filter-Hotels) ## Frequently asked questions ### What is the best area to stay in Winchester? > This area is the heart of Winchester, Illinois, and offers the most convenience for visitors. The town square is a central point, surrounded by local businesses, and the general layout is easy to navigate on foot. You'll find a few local eateries and shops within a short stroll. > > > For travellers looking for a straightforward and relaxing visit, staying in the town centre is ideal. It provides easy access to the few local attractions, such as the historic Winchester Public Library and the Scott County Courthouse, both located near the square. It's a good base for exploring the town on foot. > > > Families might also find this area suitable, as the convenience of having everything close by simplifies logistics. ### When is the best time to go to Winchester? > These periods offer pleasant weather, with comfortable temperatures that are ideal for exploring the local area and enjoying outdoor activities. Spring brings blooming landscapes, while autumn provides beautiful fall foliage, making both seasons particularly scenic. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? ### How much is the nightly rate at a Winchester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Alsey Hotels ](https://www.expedia.ca/Alsey-Hotels.d3000346086.Travel-Guide-Hotels) - [Apartments in Arcadia ](https://www.expedia.ca/Arcadia-Apartments.d553248635975871406-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Arenzville ](https://www.expedia.ca/Arenzville-Cabins.d3000346095-aaCabins.Travel-Guide-Accommodation) - [Arenzville Hotels ](https://www.expedia.ca/Arenzville-Hotels.d3000346095.Travel-Guide-Hotels) - [Ashland Hotels ](https://www.expedia.ca/Ashland-Hotels.d3000420824.Travel-Guide-Hotels) - [Beardstown Hotels ](https://www.expedia.ca/Beardstown-Hotels.d183176.Travel-Guide-Hotels) - 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