Title: Book the Best HISTORIC Hotels in Chester in 2026 | 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) ![View of a serene sunset over the Mississippi River with a bridge and a boat, Chester, United States.](https://images.trvl-media.com/place/6139861/daaedb53-d06a-4dd2-a501-e90fa192b410.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Chester, IL from CA $227 - ![](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 Historic Hotels Tonight [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester historic hotels ![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) ![Exterior](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/1422cf76_edited_0171.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 stayed here. King bed. Sleeps 4 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Rivertown-Retreat-Historic-Dufour-House-Circa-1800Downtown-District-Sleeps-4.h106052541.Hotel-Information) Ste. Genevieve 10/10 Exceptional (18) "Great historic property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rhonda R. CA $154 CA $284 total includes taxes & fees Dec 29 - Dec 30 [](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) ![Exterior](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/46dd8c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/d1990eb4.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! [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h42533836.Hotel-Information) Frohna 10/10 Exceptional (32) "Hosts were great. I just wish they had a second bath or atleast a larger bathroom. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis H. CA $130 CA $227 total includes taxes & fees Jan 1 - Jan 2, 2026 [](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) ![Smart TV, DVD player, video library](https://images.trvl-media.com/lodging/24000000/23140000/23139500/23139432/17e1434d.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) ### Beautiful Modern Loft In Wine Country! [](https://www.expedia.ca/Ste-Genevieve-Hotels-Beautiful-Modern-Loft-In-Wine-Country.h23139432.Hotel-Information) Ste. Genevieve 10/10 Exceptional (271) "Loved our stay here! Thoughtful amenities on a beautiful property. Great communication with host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elsie H. CA $202 CA $247 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Beautiful-Modern-Loft-In-Wine-Country.h23139432.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/b4be75d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/49f831a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/2790b148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/56b30b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peter Ray House [](https://www.expedia.ca/Maeystown-Hotels-Peter-Ray-House.h67672168.Hotel-Information) Maeystown 10/10 Exceptional (70) "The house was wonderful, the town was delightful, and the people were very friendly! We can’t wait for our next trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $185 CA $306 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Maeystown-Hotels-Peter-Ray-House.h67672168.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=2026-01-10&endDate=2026-01-11®ionId=6139861&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Microtel Inn & Suites by Wyndham Sainte Genevieve](https://images.trvl-media.com/lodging/1000000/430000/426000/425932/96e79bac_y.jpg) ### Microtel Inn & Suites by Wyndham Sainte Genevieve 10/10 Excellent "Excellent " [](https://expedia.ca/Ste-Genevieve-Hotels-Microtel-Inn-Suites-By-Wyndham-Sainte-Genevieve.h425932.Hotel-Information) ![Baymont by Wyndham Chester IL](https://images.trvl-media.com/lodging/1000000/10000/1700/1699/19091438_y.jpg) ### Baymont by Wyndham Chester IL 10/10 Excellent "The hotel has been declining in recent years but the new management is working to make things better and they are doing a great job. Our room was very comfortable and clean. The staff were very friendly and helpful. It was an enjoyable experience and we will stay here again. " [](https://expedia.ca/Chester-Hotels-Baymont-By-Wyndham-Chester-IL.h1699.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Chester? ### What are the most important historical places and other sights to visit in Chester? ### What is a historic hotel like in Chester? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Chester have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Farmstay in Ava ](https://www.expedia.ca/Ava-Agritourism.d3000420830-aaAgritourism.Travel-Guide-Accommodation) - [Apartments in Ava ](https://www.expedia.ca/Ava-Apartments.d3000420830-aaApartments.Travel-Guide-Accommodation) - [B&B in Ava ](https://www.expedia.ca/Ava-Bed-And-Breakfast.d3000420830-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Ava ](https://www.expedia.ca/Ava-Guest-Houses.d3000420830-aaGuestHouses.Travel-Guide-Accommodation) - 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