Title: Visit Winterset: Best of Winterset Tourism | Expedia Travel Guide - 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)[Winterset Vacation Packages](https://expedia.ca/Winterset.d181516.Destination-Travel-Guides) # Winterset ## Travel Guide ![hogback covered bridge, summer](https://images.trvl-media.com/place/181516/90035273-eecd-464a-9310-9199852de9b9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![hogback covered bridge, summer](https://images.trvl-media.com/place/181516/90035273-eecd-464a-9310-9199852de9b9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Hogback Bridge over North River - Winterset, Iowa](https://images.trvl-media.com/place/181516/606f5a08-a1cc-4347-86f1-a152642bbaad.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Hogback Bridge, Covered Bridges Scenic Byway, Iowa](https://images.trvl-media.com/place/181516/e1a24255-8145-418f-b0ae-d93c92c4554d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![#adventure Built in 1883 by Harvey P. Jones and George K. Foster, Roseman is 107 feet in length and sits in its original location. It was renovated in 1992 at a cost of $152,515. In Robert James Waller’s novel, The Bridges of Madison County, and the movie of the same name, Roseman is the bridge Robert Kincaid seeks when he stops at Francesca Johnson’s home for directions. It is also where Francesca leaves her note inviting him to dinner. Also known as the “haunted” bridge, Roseman is where two sheriff’s posses trapped a county jail escapee in 1892. It is said the man rose up straight through the roof of the bridge, uttering a wild cry, and disappeared. He was never found, and it was decided that anyone capable of such a feat must be innocent.](https://images.trvl-media.com/place/181516/0db6789c-d6ae-4170-b40d-d23684e3e99d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Winterset Things to do - Winterset Hotel Deals - Vacation Rentals in Winterset ![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 CA $117 CA $132 total Feb 22 - Feb 23 includes taxes & fees Book a stay at this business-friendly hotel in Winterset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 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=22%2F02%2F2026&endDate=23%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 CA $196 CA $220 total Feb 15 - Feb 16 includes taxes & fees Book a stay at this luxury hotel in Des Moines. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ... 9.4/10 Exceptional! (1,081 reviews) The room was very clean Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%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 CA $122 CA $137 total Feb 15 - Feb 16 includes taxes & fees Book a stay at this business-friendly hotel in Des Moines. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 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.DestinationExperience&startDate=11%2F02%2F2026&endDate=12%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. ![The Little Brick House - Walkable to the Square Dining & Shopping](https://images.trvl-media.com/lodging/121000000/120280000/120275700/120275632/w1175h762x2y0-d258b5e2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Little Brick House - Walkable to the Square Dining & Shopping Winterset IA Stay at this vacation home in Winterset. Enjoy laundry facilities and air conditioning. Popular attractions John Wayne Birthplace Museum and Cutler-Donahoe Covered ... 10/10 Exceptional! (5 reviews) An absolutely wonderful place to stay. Comfortable beds, great living room space to relax, and although we didn't really use the kitchen, it was one of the best stocked ones in all of our stays in VRBOs. Definitely will stay here again when in the area! Reviewed on Jan 12, 2026 [](https://expedia.ca/Winterset-Hotels-The-Little-Brick-House-Walkable-To-The-Square-Dining-Shopping.h120275632.Hotel-Information) ![LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS!](https://images.trvl-media.com/lodging/35000000/34150000/34149700/34149649/647e4df9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### LUXURY GETAWAY! ARCADE, POOL TBL, PING PONG, HOT TUB, DECK! ACCESS TO POOLS! Waukee IA Book a stay at this golf vacation home in Waukee. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Jordan Creek Town Center and Hawthorne ... 9.6/10 Exceptional! (73 reviews) We had lots of fun. Several things broken and not real clean. But still had lots of fun. Reviewed on Jan 5, 2026 [](https://expedia.ca/Des-Moines-Hotels-CHEAP-WEEKDAYS-ARCADE.h34149649.Hotel-Information) ![SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!!](https://images.trvl-media.com/lodging/92000000/91740000/91731000/91730930/cfbdd00a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SO MUCH FUN! ARCADE, PL TBL, PNG PNG, YARD GAMES, INDOOR AND OUTDOOR POOLS!! Des Moines IA Book a stay at this family-friendly vacation home in Des Moines. Enjoy free WiFi, a fitness center, and laundry facilities. Our guests praise the helpful staff ... 9.2/10 Wonderful! (68 reviews) The house was extremely well-stocked and had tons of space for our group. Everyone enjoyed the activities in the basement! Reviewed on Jan 21, 2026 [](https://expedia.ca/Des-Moines-Hotels-SO-MUCH-FUN-ARCADE.h91730930.Hotel-Information) [See all properties in Winterset](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=181516&sort=VACATION_RENTAL) 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. ## Check Winterset hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=2026-02-10&endDate=2026-02-11)[Feb 10 - Feb 11](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=2026-02-10&endDate=2026-02-11) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=2026-02-11&endDate=2026-02-12)[Feb 11 - Feb 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=2026-02-11&endDate=2026-02-12) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=181516&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) ### Popular places to visit ![An Old Red Covered Bridge Over A River](https://images.trvl-media.com/place/6106002/bc7c33e9-3c64-4891-af8a-c0a6aa038c0b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Roseman Bridge You can learn about the history of Winterset with a stop at Roseman Bridge. Make some time to visit the monuments while you're in the area. [](https://expedia.ca/Roseman-Bridge-Winterset.d6106002.Vacation-Attraction) ![Clark Tower is one of my favorite spots. 3 levels, spiral stairs and beautiful stone. ](https://images.trvl-media.com/place/181516/baa8c8c4-f22a-403f-ac61-135bce9a9e0d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Clark Tower You can find out about the history of Winterset with a stop at Clark Tower. Make some time to visit the shops while you're in the area. [](https://expedia.ca/Clark-Tower-Winterset.d553248621564886258.Vacation-Attraction) ![Cedar Bridge under trees - Winterset, Iowa](https://images.trvl-media.com/place/6106000/34284961-51f0-4352-b93e-3261b4a6419c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cedar Bridge You can learn about the history of Winterset when you stop by Cedar Bridge. Make some time to visit the monuments while you're in the area. [](https://expedia.ca/Cedar-Bridge-Winterset.d6106000.Vacation-Attraction) ![An Old Red Covered Bridge](https://images.trvl-media.com/place/6105998/a0690ba6-fa48-4b31-81ec-dda70e39943c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Holliwell Bridge Learn about the local history of Winterset when you spend time at Holliwell Bridge. Make some time to visit the monuments while you're in the area. [](https://expedia.ca/Holliwell-Bridge-Winterset.d6105998.Vacation-Attraction) #### John Wayne Birthplace Museum You can spend an afternoon browsing the exhibits at John Wayne Birthplace Museum in Winterset. While you're in the area, wander around the natural setting. [](https://expedia.ca/John-Wayne-Birthplace-Museum-Winterset.d6105996.Vacation-Attraction) #### Madison County Courthouse Madison County Courthouse is just one of the places to see in Winterset, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the natural setting. [](https://expedia.ca/Madison-County-Courthouse-Winterset.d6106008.Vacation-Attraction) - Cities near Winterset - Places of interest - [West Glen Town Center ](https://expedia.ca/West-Glen-Town-Center-Des-Moines.d6220506.Vacation-Attraction) - [Des Moines Art Center ](https://expedia.ca/Des-Moines-Art-Center-Des-Moines.d6075020.Vacation-Attraction) - [Sky Zone Indoor Trampoline Park ](https://expedia.ca/Sky-Zone-Indoor-Trampoline-Park-Des-Moines.d553248621532649070.Vacation-Attraction) ![](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