Title: Winterset Vacation Packages & Trips 2026 from CA $1,283 | 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. ![TownePlace Suites by Marriott - Des Moines Urbandale](https://images.trvl-media.com/lodging/2000000/1770000/1764300/1764292/7a25013b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### TownePlace Suites by Marriott - Des Moines Urbandale CA $1,283 per person Apr 16 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Des Moines (DSM) 8.6/10 Excellent! (762 reviews) Tommy was clean and just what we needed. Reviewed on Feb 1, 2026 ![Hotel Fort Des Moines, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/10000/9400/9375/9e4e0ef2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Fort Des Moines, Curio Collection by Hilton Downtown Des Moines CA $1,630 per person Apr 16 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Des Moines (DSM) 9.6/10 Exceptional! (1,037 reviews) Room was great staff were very kind had to leave due to family emergency huge thank you to the staff that helped out that night and got my car out of valet for me will be coming back soon!! Reviewed on Feb 1, 2026 ![Hilton Des Moines Downtown](https://images.trvl-media.com/lodging/22000000/21330000/21321600/21321542/1993f6e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Des Moines Downtown Downtown Des Moines CA $1,749 per person Apr 16 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Des Moines (DSM) 9/10 Wonderful! (1,000 reviews) Great location and parking accommodation. Reviewed on Jan 28, 2026 ![AC Hotel Des Moines East Village](https://images.trvl-media.com/lodging/17000000/16530000/16525800/16525760/c1989ee2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### AC Hotel Des Moines East Village Downtown Des Moines CA $1,911 per person Apr 16 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Des Moines (DSM) 9.2/10 Wonderful! (400 reviews) Great hotel in a great location in downtown Des Moines Reviewed on Feb 4, 2026 ![Home2 Suites by Hilton Des Moines at Drake University](https://images.trvl-media.com/lodging/49000000/48260000/48251500/48251406/b9f3330e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Home2 Suites by Hilton Des Moines at Drake University Drake CA $1,404 per person Apr 16 - Apr 23 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Des Moines (DSM) 9.4/10 Exceptional! (1,001 reviews) Clean, spacious, great amenities, and the sheets were super soft. Reviewed on Feb 5, 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 $116 CA $130 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! (1,076 reviews) It is a pleasure to stay here! Reviewed on Jan 30, 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 9 - Feb 10 includes taxes & fees 9.2/10 Wonderful! (1,008 reviews) Room and hotel was very clean, staff were friendly, would definitely stay again! Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=48251406&PinnedHotelID=48251406&HadPinnedHotel=true®ionId=181516) [See all 555 properties in Winterset](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F02%2F2026&endDate=08%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