Title: Chester Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d553248634983489687.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d553248634983489687.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d553248634983489687.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ![](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=PKG_SPRING_PROMO_553248634983489687) ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![AmericInn by Wyndham Osage](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027430/1e38176f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### AmericInn by Wyndham Osage 2212 Highway 218 Osage IA Fully refundableReserve now, pay when you stay CA $124 CA $139 total Mar 8 - Mar 9 includes taxes & fees 9.4/10 Exceptional! (280 reviews) Room was clean and at good room temperature despite the bitter cold (outside) conditions. friendly and welcoming staff Reviewed on Jan 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=5027430&PinnedHotelID=5027430&HadPinnedHotel=true®ionId=553248634983489687) ![Super 8 by Wyndham Cresco IA](https://images.trvl-media.com/lodging/1000000/860000/856400/856334/36399612_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Super 8 by Wyndham Cresco IA 511 Second Ave SE, Hwy 9 & 5th Street Cresco IA Fully refundableReserve now, pay when you stay CA $89 CA $100 total Mar 8 - Mar 9 includes taxes & fees 8.4/10 Very Good! (491 reviews) Yea Reviewed on Jan 28, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=856334&PinnedHotelID=856334&HadPinnedHotel=true®ionId=553248634983489687) ![Country Trails Inn & Suites ](https://images.trvl-media.com/lodging/101000000/100370000/100366400/100366373/f1672741_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Trails Inn & Suites 809 U.S. 52 Preston MN Fully refundableReserve now, pay when you stay CA $172 CA $190 total Feb 15 - Feb 16 includes taxes & fees 9.4/10 Exceptional! (103 reviews) Room was clean and staff were very friendly. Reviewed on Jan 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=100366373&PinnedHotelID=100366373&HadPinnedHotel=true®ionId=553248634983489687) [See all 24 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F02%2F2026&endDate=16%2F02%2F2026®ionId=553248634983489687) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app