Title: Chester, IL Cottage Rentals from $222 | 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 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6139861&startDate=2026-06-19&endDate=2026-06-21&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) "Great historic property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rhonda R. $205 nightly $222 total Mar 2 - Mar 3 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) ![Smart TV](https://images.trvl-media.com/lodging/121000000/120600000/120598000/120597974/e81c863e.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) ![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) ### 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 Mar 2 - Mar 3 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) ![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) ![Private kitchen](https://images.trvl-media.com/lodging/124000000/123910000/123907100/123907073/85e7ef3a.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. $318 nightly $337 total Mar 2 - Mar 3 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=2026-03-15&endDate=2026-03-16®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=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&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=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&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=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&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=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&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=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&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 ![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 "Clean Room, staff always ready to assist with any issues." [](https://expedia.com/Chester-Hotels-Baymont-By-Wyndham-Chester-IL.h1699.Hotel-Information) ![Super 8 by Wyndham Okawville](https://images.trvl-media.com/lodging/1000000/460000/459800/459708/f757e9ca_y.jpg) ### Super 8 by Wyndham Okawville 10/10 Excellent "I Always stay here when traveling this way. The room is clean and the staff are great" [](https://expedia.com/Carlyle-Lake-Hotels-Super-8-By-Wyndham-Okawville.h459708.Hotel-Information) ### 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) ![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) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 22 | | ----------------- | ----------- | | Accommodation | 11 Cottages | | Lowest Price | $222 | | 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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