Title: Book the Best Chester WINERY Hotels in 2025 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6139861.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6139861.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6139861.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6139861.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/winery.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chester, IL from CA $109 ![](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 ## Check availability on Chester Winery Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Winery Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/692700/692668/372ece1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/692700/692668/d669a1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/700000/692700/692668/d1c4344d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/700000/692700/692668/74f16cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Briarwood Inn of Sparta Sparta 7.4/10 Good (119) "It’s the mid level hotel in town. Clean and gets the job done. " CA $98 CA $109 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Chester-Hotels-Briarwood-Inn-Of-Sparta.h692668.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/1000000/10000/5600/5523/5f8a3296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/10000/5600/5523/96723311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/5600/5523/6e9d01e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5600/5523/540bf915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Festus Festus 6.8/10 (899) "The floors were dirty. Trash all over. Indoor pool was freezing. Breakfast was either empty or still frozen (sausage, hash browns). Apparently Baymont just acquired this property, but much more work should have been done before opening. The bed was comfortable with clean sheets though. The toilet had to be flushed 6x just to get rid of toilet paper. " CA $113 CA $130 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Festus-Hotels-Baymont-By-Wyndham-Festus.h5523.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/e186477c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/298cfcd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/52de7a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/c3fbac48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ⚜️Rivertown Retreat⚜️ Lewis & Clark: King Bed Sleeps 4 Ste. Genevieve 10/10 Exceptional (13) "Amazing property super quiet and chill." CA $199 CA $335 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Rivertown-Retreat-Historic-Dufour-House-Circa-1800Downtown-District-Sleeps-4.h106052541.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/52e075c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/e5b0b4ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/46dd8c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/f5ad31e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Weber Farm - Enjoy a beautiful 100 acre farm! Frohna 10/10 Exceptional (31) "Hosts were great. I just wish they had a second bath or atleast a larger bathroom. " CA $158 CA $258 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h42533836.Hotel-Information) ![1 bedroom, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/24000000/23140000/23139500/23139432/86d734a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23140000/23139500/23139432/81907571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/24000000/23140000/23139500/23139432/08a1bdfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23140000/23139500/23139432/f03e39eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Modern Loft In Wine Country! Ste. Genevieve 10/10 Exceptional (267) "Beautiful loft on beautiful property!" CA $207 CA $250 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Beautiful-Modern-Loft-In-Wine-Country.h23139432.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67140000/67135900/67135817/9f1b48ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67140000/67135900/67135817/w1170h1560x0y486-7708b776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67140000/67135900/67135817/5aaf2aaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/68000000/67140000/67135900/67135817/6b5538e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Doves Nest Guest House
Tranquil & Relaxing Ste. Genevieve 9.8/10 Exceptional (48) "Outstanding! I highly recommend to everyone! So well decorated with every amenity! Great location and easy walk to restaurants and activities and shopping! Great hosts!" CA $176 CA $318 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Doves-Nest-Guest-Housebr-Tranquil-Relaxing.h67135817.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/89000000/89000000/88996300/88996203/93328db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/89000000/88996300/88996203/w507h683x259y0-84bc4b01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/89000000/88996300/88996203/07bdf180_edited_b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/89000000/88996300/88996203/w525h683x259y0-930fe938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Little Brick House on Main (1865)” Ste. Genevieve 10/10 Exceptional (56) "Great place to stay!" CA $166 CA $222 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Little-Brick-House.h88996203.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113890000/113885400/113885316/1b67e3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/114000000/113890000/113885400/113885316/43749169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113890000/113885400/113885316/16fec408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113890000/113885400/113885316/a369c401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside. Bloomsdale 10/10 Exceptional (5) "What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! " CA $231 CA $363 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bloomsdale-Hotels-Charming-1-Bedroom-Home-In-The-Peaceful-Countryside-Of-Bloomsdale.h113885316.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39500000/39493900/39493801/bc6052c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39500000/39493900/39493801/4647849f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/40000000/39500000/39493900/39493801/5c6ced68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39500000/39493900/39493801/fb9a776c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silo Farm Haus- located in the heart of wine country! Ste. Genevieve 10/10 Exceptional (145) "A awesome place to stay will be back" CA $335 CA $479 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Silo-Farm-Haus-Located-In-The-Heart-Of-Wine-Country.h39493801.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113880000/113879200/113879109/df663fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113880000/113879200/113879109/f41c0202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113880000/113879200/113879109/e64cef9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113880000/113879200/113879109/08a25916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten. New Offenburg 10/10 Exceptional (3) "Relaxing setting between Farmington and St Genevieve. Both towns are rich in history and have small town charm. " CA $189 CA $387 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Peaceful-3-Bedroom-House-With-WiFi-And-AC-In-Lovely-New-Offenburg.h113879109.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=2025-10-27&endDate=2025-10-28®ionId=6139861&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Microtel Inn & Suites by Wyndham Sainte Genevieve](//images.trvl-media.com/lodging/1000000/430000/426000/425932/96e79bac_y.jpg) ### Microtel Inn & Suites by Wyndham Sainte Genevieve 10/10 Excellent "Great location and safe area. Room was very comfortable and clean. Beds were comfortable and shower had great water pressure. Enjoyed the stay." 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