Title: Chester Cottages from CA $289 | 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) ![](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__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 prices for these dates In two weeks [Mar 6 - Mar 8](https://www.expedia.ca/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.ca/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.ca/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.ca/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) ![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) ![Interior](https://images.trvl-media.com/lodging/107000000/106060000/106052600/106052541/d9c7cec9.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 (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. CA $159 CA $289 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/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/e81c863e.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.ca/Waterloo-Hotels-Charming-2-Bedroom-Cottage-With-Patio-In-Waterloo.h120597974.Hotel-Information) Waterloo CA $207 CA $480 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/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) ![Private kitchen](https://images.trvl-media.com/lodging/124000000/123910000/123907100/123907073/85e7ef3a.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.ca/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. CA $202 CA $473 total includes taxes & fees Feb 24 - Feb 25 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04®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.ca/deals?rfrr=AA_SPRING_PROMO_6139861) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Illinois%2C+United+States+of+America®ionId=6139861&latLong=37.913663%2C-89.82205&adults=2&startDate=2026-05-18&d1=2026-05-18&endDate=2026-05-21&d2=2026-05-21&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d6139861-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d6139861-aaCottages.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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.ca/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.ca/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.ca/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.ca/Perryville-Hotels-Holiday-Inn-Express-Suites-Perryville.h20115319.Hotel-Information) ### Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "Absolutely perfect stay! Beautiful clean cabin, fantastic views, so private and lovely. The amenities were great, and from beginning to end our stay was everything we wanted. " [](https://expedia.ca/French-Village-Hotels-Postcard-Cabins-St-Francois.h110550817.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.ca/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.ca/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.ca/Perryville-Hotels-Days-Inn-By-Wyndham-Perryville.h10352.Hotel-Information) ![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 "The Microtel is a nice, relatively inexpensive place to stay in Ste. Genevieve. Breakfast options are somewhat limited. Overall, it is a very good value for the price." [](https://expedia.ca/Ste-Genevieve-Hotels-Microtel-Inn-Suites-By-Wyndham-Sainte-Genevieve.h425932.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 22 | | ----------------- | ----------- | | Accommodation | 11 Cottages | | Lowest Price | CA $289 | | Highest Price | CA $480 | ## 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 - [5 Star Hotels in Pomona ](https://www.expedia.ca/5Star-Pomona-Hotels.s50-0-d553248635592817265.Travel-Guide-Filter-Hotels) - [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) - 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