Title: Chester, IL Cottage Rentals from $213 | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx6139861)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6139861.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d6139861.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6139861.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6139861.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/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) ![](https://images.trvl-media.com/place/6139861/daaedb53-d06a-4dd2-a501-e90fa192b410.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester cottages ![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) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/8ecfca12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/d9c7cec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/f4915375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4 [](https://www.expedia.com/Ste-Genevieve-Hotels-Rivertown-Retreat-Historic-Dufour-House-Circa-1800Downtown-District-Sleeps-4.h106052541.Hotel-Information) Ste. Genevieve 10/10 Exceptional (22 reviews) "Charming historic home!! We had a wonderful stay!! Perfect location!! Wish we could have stayed longer!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken J. $213 nightly $213 total Feb 21 - Feb 22 Total with taxes and fees [](https://www.expedia.com/Ste-Genevieve-Hotels-Rivertown-Retreat-Historic-Dufour-House-Circa-1800Downtown-District-Sleeps-4.h106052541.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120600000/120598000/120597974/w1023h682x1y1-087e4f9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120600000/120598000/120597974/w1023h682x1y1-939ecfbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/121000000/120600000/120598000/120597974/w1023h682x1y1-dc6621ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120600000/120598000/120597974/ab8ca423.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Charming 2-bedroom cottage with Patio in Downtown Waterloo [](https://www.expedia.com/Waterloo-Hotels-Charming-2-Bedroom-Cottage-With-Patio-In-Waterloo.h120597974.Hotel-Information) Waterloo $330 nightly $350 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Waterloo-Hotels-Charming-2-Bedroom-Cottage-With-Patio-In-Waterloo.h120597974.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123910000/123907100/123907073/4aec557b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/124000000/123910000/123907100/123907073/85e7ef3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/124000000/123910000/123907100/123907073/cb5dc41e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123910000/123907100/123907073/af91ddb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Speakeasy Cottage [](https://www.expedia.com/Waterloo-Hotels-NEW-Speakeasy-Cottage-Available-For-Christmas.h123907073.Hotel-Information) Waterloo 10/10 Exceptional (2 reviews) "We loved our stay! Spacious, decor wonderful,Convenient to restaurants and coffee cafes The owner was easy to communicate with and hands on We were snowed in and she helped us in every way Look forward to a return visit " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas L. $325 nightly $344 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Waterloo-Hotels-NEW-Speakeasy-Cottage-Available-For-Christmas.h123907073.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=2026-03-06&endDate=2026-03-07®ionId=6139861&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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.com/deals?rfrr=AA_SPRING_PROMO_6139861) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-21&d1=2026-05-21&endDate=2026-05-24&d2=2026-05-24&lodging=APART_HOTEL) ![](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%2FChester-Cottages.d6139861-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d6139861-aaCottages.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ### Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "Todo perfecto!" [](https://expedia.com/French-Village-Hotels-Postcard-Cabins-St-Francois.h110550817.Hotel-Information) ![Baymont by Wyndham Festus](https://images.trvl-media.com/lodging/1000000/10000/5600/5523/219ce8d0_y.jpg) ### Baymont by Wyndham Festus 10/10 Excellent "Everything was great. I enjoyed my stay " [](https://expedia.com/Festus-Hotels-Baymont-By-Wyndham-Festus.h5523.Hotel-Information) ![Super 8 by Wyndham Perryville](https://images.trvl-media.com/lodging/1000000/670000/664100/664059/f824aec9_y.jpg) ### Super 8 by Wyndham Perryville 10/10 Excellent "The carpet in the room and halls looked new which says a lot. I would stay there again. " [](https://expedia.com/Perryville-Hotels-Super-8-By-Wyndham-Perryville.h664059.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 rooms were extremely clean & the staff was supper attentive and nice!" [](https://expedia.com/Chester-Hotels-Baymont-By-Wyndham-Chester-IL.h1699.Hotel-Information) ![Private Cabin with Pond on Family Farm](https://images.trvl-media.com/lodging/94000000/93760000/93751900/93751850/5a7f6384_y.jpg) ### Private Cabin with Pond on Family Farm 10/10 Excellent "Tom was very welcoming, when we arrived, he escorted us to the cabin. Upon entry he explained all the features of the cabin and showed us how to operate everything. The cabin is fully equipped with everything you could possibly need." [](https://expedia.com/Private-Cabin-On-Family-Farm.h93751850.Hotel-Information) ![Holiday Inn Express & Suites Perryville by IHG](https://images.trvl-media.com/lodging/21000000/20120000/20115400/20115319/68f46185_y.jpg) ### Holiday Inn Express & Suites Perryville by IHG 10/10 Excellent "Rooms are huge, great for family traveling " [](https://expedia.com/Perryville-Hotels-Holiday-Inn-Express-Suites-Perryville.h20115319.Hotel-Information) ![Red Bud Country Inn](https://images.trvl-media.com/lodging/105000000/104320000/104319800/104319742/3eb49477_y.jpg) ### Red Bud Country Inn 10/10 Excellent "Room was great. Staff Stupendous. Recommend friends to stay." [](https://expedia.com/Red-Bud-Hotels-Red-Bud-Country-Inn.h104319742.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Festus - St. Louis South](https://images.trvl-media.com/lodging/1000000/50000/42200/42120/1887aa70_y.jpg) ### La Quinta Inn & Suites by Wyndham Festus - St. Louis South 10/10 Excellent "Great staff, room was clean and comfortable. Clean and fully stocked breakfast." [](https://expedia.com/Farmington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Festus-St-Louis-South.h42120.Hotel-Information) ![Days Inn by Wyndham Perryville](https://images.trvl-media.com/lodging/1000000/20000/10400/10352/f6ab26a4_y.jpg) ### Days Inn by Wyndham Perryville 10/10 Excellent "Great people there" [](https://expedia.com/Perryville-Hotels-Days-Inn-By-Wyndham-Perryville.h10352.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 22 | | ----------------- | ----------- | | Accommodation | 11 Cottages | | Lowest Price | $213 | | Highest Price | $350 | ## Frequently asked questions ### Why book your cottage in Chester with Expedia? ### How can I find cheap cottages in Chester? ### What is there to do in Chester near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Popeye Museum ](https://www.expedia.com/Popeye-Museum-Hotels.0-l553248621532655787-0.Travel-Guide-Filter-Hotels) - [Hotels near Elzie C. 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