Title: Winterset Vacation Packages & Trips 2026 from CA $814 | Expedia.ca [Hotels in Winterset](https://expedia.ca/Winterset-Hotels.d181516.Travel-Guide-Hotels)[Vacation Rentals in Winterset](https://expedia.ca/Winterset-Vacation-Rentals.d181516.Travel-Guide-VacationRentals)[Flights to Winterset](https://expedia.ca/Cheap-Flights-To-Winterset.d181516.Travel-Guide-Flights)[Winterset Car Rentals](https://expedia.ca/Car-Rentals-In-Winterset.d181516.Car-Rental-Guide) ![](https://images.trvl-media.com/place/181516/90035273-eecd-464a-9310-9199852de9b9.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winterset 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 #### Your Winterset Vacation Book a Winterset vacation package and get set for an awesome adventure. Famous for its rich history and friendly locals, there's loads to like about this fascinating city. Every trip to Winterset needs a well-planned itinerary. Fill yours with leading attractions like [John Wayne Birthplace Museum](https://www.expedia.ca/John-Wayne-Birthplace-Museum-Winterset.d6105996.Vacation-Attraction), [The Winterset Stage](https://www.expedia.ca/The-Winterset-Stage-Winterset.d553248621561929561.Vacation-Attraction) and [Clark Tower](https://www.expedia.ca/Clark-Tower-Winterset.d553248621564886258.Vacation-Attraction). Stop dreaming and start traveling. Check out the wide range of options on Expedia today and finally put your Winterset vacation plans into motion! ## Top Winterset Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Studio 6 Altoona, IA - Des Moines East](https://images.trvl-media.com/lodging/75000000/74060000/74056700/74056667/f4d98796_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Studio 6 Altoona, IA - Des Moines East CA $814 per person Mar 15 - Mar 17 found 18 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Des Moines (DSM) 7.4/10 Good! (439 reviews) Even though the room is non-smoking, outside the room is full of cigarettes smell. The AC unit made a loud noise. Reviewed on Jan 28, 2026 ![Holiday Inn Downtown - Mercy Area by IHG](https://images.trvl-media.com/lodging/1000000/20000/18900/18835/822a9f1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Downtown - Mercy Area by IHG Downtown Des Moines CA $883 per person Mar 15 - Mar 17 found 18 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Des Moines (DSM) 8/10 Very Good! (1,001 reviews) Hotel was good option for walking to Casey Center for Paul McCartney concert. Lobby was filled with concert goers end of evening, and it took hotel over 30 minutes to open stairwell. People were piled up in lobby, security was nowhere to be found, and front desk didn't have keys to open stairwell. People were tired, had to use bathroom, etc, and it took too long to accommodate the guests needs. Reviewed on Nov 16, 2025 ![Hyatt Place West Des Moines Jordan Creek](https://images.trvl-media.com/lodging/17000000/16120000/16112600/16112546/f70b7069_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place West Des Moines Jordan Creek CA $878 per person Mar 15 - Mar 17 found 18 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Des Moines (DSM) 9.2/10 Wonderful! (1,004 reviews) The room was well maintained, the staff were friendly, and they printed a few documents for me at no charge! Breakfast was really nice. Reviewed on Feb 4, 2026 ![Stoney Creek Hotel Des Moines - Johnston](https://images.trvl-media.com/lodging/2000000/1160000/1152300/1152222/8b967b66_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stoney Creek Hotel Des Moines - Johnston CA $864 per person Mar 15 - Mar 17 found 18 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Des Moines (DSM) 9/10 Wonderful! (1,775 reviews) Allways helpfull, clean, nice pool, hot tub area. Reviewed on Feb 4, 2026 ![Motel 6 Altoona, IA - Des Moines East](https://images.trvl-media.com/lodging/1000000/1000000/996300/996237/b0bc3d3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Motel 6 Altoona, IA - Des Moines East CA $815 per person Mar 15 - Mar 17 found 18 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Des Moines (DSM) 6/10 (1,001 reviews) Everything was great! Reviewed on Feb 3, 2026 ## Ready to book your vacation to Winterset? Choose your dates ## Winterset Hotel Deals ![Cobblestone Inn & Suites - Winterset, IA](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/f46e6906_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cobblestone Inn & Suites - Winterset, IA 1304 North 4th Avenue Winterset IA Fully refundableReserve now, pay when you stay CA $117 CA $132 total Feb 16 - Feb 17 includes taxes & fees 9.2/10 Wonderful! (716 reviews) Clean rooms. Friendly staff and easy to find Reviewed on Jan 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=10446857&PinnedHotelID=10446857&HadPinnedHotel=true®ionId=181516) ![Hotel Fort Des Moines, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/10000/9400/9375/9e4e0ef2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Fort Des Moines, Curio Collection by Hilton 1000 Walnut St Des Moines IA Fully refundableReserve now, pay when you stay CA $184 CA $206 total Feb 25 - Feb 26 includes taxes & fees 9.4/10 Exceptional! (1,081 reviews) The room was very clean Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=9375&PinnedHotelID=9375&HadPinnedHotel=true®ionId=181516) ![Home2 Suites by Hilton Des Moines at Drake University](https://images.trvl-media.com/lodging/49000000/48260000/48251500/48251406/b9f3330e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Home2 Suites by Hilton Des Moines at Drake University 2650 University Ave. Des Moines IA Fully refundableReserve now, pay when you stay CA $122 CA $137 total Feb 15 - Feb 16 includes taxes & fees 9.2/10 Wonderful! (1,011 reviews) Clean, spacious, great amenities, and the sheets were super soft. Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=48251406&PinnedHotelID=48251406&HadPinnedHotel=true®ionId=181516) [See all 560 properties in Winterset](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=181516) 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