Title: Book the Best Chester FAMILY FRIENDLY Hotels from CA $100 - Kid-Friendly Hotels in Chester, IL | 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 availability on Chester Family Hotels Tonight [Mar 1 - Mar 2](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2026-03-01&endDate=2026-03-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Mar 2 - Mar 3](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2026-03-02&endDate=2026-03-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6139861&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Chester family-friendly hotels ![Free buffet breakfast](https://images.trvl-media.com/lodging/2000000/1700000/1691200/1691121/331aa35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/2000000/1700000/1691200/1691121/456e3083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1700000/1691200/1691121/93f13efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/2000000/1700000/1691200/1691121/2635c5bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Sparta by IHG [](https://www.expedia.ca/Chester-Hotels-Holiday-Inn-Express-Hotel-Suites-Sparta.h1691121.Hotel-Information) Sparta 9.2/10 Wonderful (383 reviews) - Family fun for all ages awaits with indoor pool adventures and free deluxe breakfast at this welcoming Sparta retreat. CA $149 CA $165 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Chester-Hotels-Holiday-Inn-Express-Hotel-Suites-Sparta.h1691121.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20120000/20115400/20115319/469821a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20120000/20115400/20115319/0c87c756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20120000/20115400/20115319/1d457549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/21000000/20120000/20115400/20115319/2b5bb07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Perryville by IHG [](https://www.expedia.ca/Perryville-Hotels-Holiday-Inn-Express-Suites-Perryville.h20115319.Hotel-Information) Perryville 9.2/10 Wonderful (561 reviews) CA $140 CA $161 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Perryville-Hotels-Holiday-Inn-Express-Suites-Perryville.h20115319.Hotel-Information) ![Studio Suite, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459708/c767f3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459708/f757e9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/460000/459800/459708/f63204c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459708/584aa2c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Okawville [](https://www.expedia.ca/Carlyle-Lake-Hotels-Super-8-By-Wyndham-Okawville.h459708.Hotel-Information) Okawville 7.4/10 Good (319 reviews) - Friendly roadside hotel offers easy family stays with cribs, breakfast, and premium TV channels for everyone's enjoyment. CA $90 CA $100 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Carlyle-Lake-Hotels-Super-8-By-Wyndham-Okawville.h459708.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/121000000/120600000/120598000/120597974/ab8ca423.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) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120600000/120598000/120597974/w1023h683x1y0-20e9dddf.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 $481 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) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/5600/5523/b5436bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Festus [](https://www.expedia.ca/Festus-Hotels-Baymont-By-Wyndham-Festus.h5523.Hotel-Information) Festus 6.8/10 (940 reviews) - Family fun guaranteed with indoor pool, game room, and free breakfast at this Festus hotel just minutes from Pevely Park. CA $105 CA $120 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Festus-Hotels-Baymont-By-Wyndham-Festus.h5523.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/65000000/64020000/64010900/64010827/279ae559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64020000/64010900/64010827/1ad35878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/65000000/64020000/64010900/64010827/e3abf9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/65000000/64020000/64010900/64010827/75aa74d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Country Home [](https://www.expedia.ca/Peaceful-Country-Home.h64010827.Hotel-Information) Marissa 10/10 Exceptional (48 reviews) CA $195 CA $348 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Peaceful-Country-Home.h64010827.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/970a0e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/f3482f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/b56eb1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/68000000/67680000/67672200/67672168/e8c84ce5.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 (72 reviews) CA $184 CA $304 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Maeystown-Hotels-Peter-Ray-House.h67672168.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/59000000/58090000/58087700/58087650/717b3c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/59000000/58090000/58087700/58087650/354167f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/59000000/58090000/58087700/58087650/c5f94d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/59000000/58090000/58087700/58087650/09eb09f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Haven Little Hidden Gem Sleeps 4 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Cozy-Haven-Little-Hidden-Gem-Sleeps-4.h58087650.Hotel-Information) Ste.Genevieve 9.8/10 Exceptional (58 reviews) CA $135 CA $291 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Ste-Genevieve-Hotels-Cozy-Haven-Little-Hidden-Gem-Sleeps-4.h58087650.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108620000/108613200/108613112/d7e4be9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108620000/108613200/108613112/6ab4b59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball](https://images.trvl-media.com/lodging/109000000/108620000/108613200/108613112/3624fba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/109000000/108620000/108613200/108613112/a82a0b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Firepit, Rooftop deck, Games & Bridal Suite and right next to The Coffee Girl [](https://www.expedia.ca/Waterloo-Hotels-Firepit.h108613112.Hotel-Information) Waterloo 10/10 Exceptional (18 reviews) CA $254 CA $552 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Waterloo-Hotels-Firepit.h108613112.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/92000000/91900000/91894300/91894271/6d5a7bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/92000000/91900000/91894300/91894271/985bc4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91900000/91894300/91894271/7f4ba1de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91900000/91894300/91894271/a519e681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farmstead home w/hot tub [](https://www.expedia.ca/Farmstead-Home-Whot-Tub.h91894271.Hotel-Information) Marissa 10/10 Exceptional (15 reviews) CA $203 CA $368 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Farmstead-Home-Whot-Tub.h91894271.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=2026-03-16&endDate=2026-03-17®ionId=6139861&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at family-friendly hotels in Chester Breakfast included Pool All-inclusive 4 stars 5 stars ![](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=AFFINITY_SPRING_PROMO_6139861) ## Top Chester Hotel Reviews ![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.ca/Carlyle-Lake-Hotels-Super-8-By-Wyndham-Okawville.h459708.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.ca/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.ca/Perryville-Hotels-Super-8-By-Wyndham-Perryville.h664059.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) ![Holiday Inn Express Hotel & Suites Sparta by IHG](https://images.trvl-media.com/lodging/2000000/1700000/1691200/1691121/331aa35f_y.jpg) ### Holiday Inn Express Hotel & Suites Sparta by IHG 10/10 Excellent "It was nice with friendly staff " [](https://expedia.ca/Chester-Hotels-Holiday-Inn-Express-Hotel-Suites-Sparta.h1691121.Hotel-Information) ## Frequently asked questions ### What's Chester like for family-friendly vacations? ### When's the best time to book a family-friendly vacation in Chester? ### What's there to see and do with your family in Chester? ## 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) - 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