Title: Book the Best HISTORIC Hotels in Winterset in 2026 | 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) ![hogback covered bridge, summer](https://images.trvl-media.com/place/181516/90035273-eecd-464a-9310-9199852de9b9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/181516/90035273-eecd-464a-9310-9199852de9b9.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 Winterset Historic Hotels Tonight [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2026-01-26&endDate=2026-01-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2026-01-27&endDate=2026-01-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=181516&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Winterset ![Exterior](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/221411cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/ebfe9fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/0d76b175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa Bed, Accessible Roll in Shower, Non Smoking | Living area](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/3f55f340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cobblestone Inn & Suites - Winterset, IA [](https://www.expedia.ca/Winterset-Hotels-Cobblestone-Inn-Suites-Winterset.h10446857.Hotel-Information) Winterset 9.2/10 Wonderful (716 reviews) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $121 CA $136 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Winterset-Hotels-Cobblestone-Inn-Suites-Winterset.h10446857.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/cf139e75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/d80624d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Walk Up](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/c74a1fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/73387cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Covered Bridge Inn [](https://www.expedia.ca/Winterset-Hotels-Covered-Bridge-Inn.h439956.Hotel-Information) Winterset 9.0/10 Wonderful (769 reviews) "Staff friendly, excellent place nice and clean, comfy and great breakfast" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Paula CA $97 CA $109 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Winterset-Hotels-Covered-Bridge-Inn.h439956.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116930000/116926300/116926284/57d42cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116930000/116926300/116926284/0dd990a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116930000/116926300/116926284/df69fb75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116930000/116926300/116926284/4d1dda04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset [](https://www.expedia.ca/Winterset-Hotels-Covered-Bridge-Haven-3-Bedroom-House-With-Themed-Rooms-In-Winterset.h116926284.Hotel-Information) Winterset 10/10 Exceptional (5 reviews) "The house was absolutely gorgeous! It was very comfortable and had everything we needed. I would most definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather G. CA $151 CA $461 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Winterset-Hotels-Covered-Bridge-Haven-3-Bedroom-House-With-Themed-Rooms-In-Winterset.h116926284.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/4886c0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/23d54adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/5da35228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/6000000/5630000/5628800/5628747/d841b08a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Hotel Casino [](https://www.expedia.ca/Osceola-Hotels-Lakeside-Hotel-Casino.h5628747.Hotel-Information) Osceola 8.0/10 Very good (1,008 reviews) "The room was clean and in a good location " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) ronald CA $101 CA $133 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Osceola-Hotels-Lakeside-Hotel-Casino.h5628747.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/530000/522700/522646/428ef378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/530000/522700/522646/aeb21d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/530000/522700/522646/cb06306c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/530000/522700/522646/e914f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Stuart [](https://www.expedia.ca/Atlantic-Hotels-AmericInn-By-Wyndham-Stuart.h522646.Hotel-Information) Stuart 8.4/10 Very good (529 reviews) "Was clean and nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $105 CA $123 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Atlantic-Hotels-AmericInn-By-Wyndham-Stuart.h522646.Hotel-Information) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/50000/49900/49826/fcd8bd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/50000/49900/49826/4622c857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/49900/49826/f005535b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49900/49826/a95f1765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn & Suites by Wyndham Des Moines Airport [](https://www.expedia.ca/Des-Moines-Hotels-Days-Inn-Suites-By-Wyndham-Des-Moines-Airport.h49826.Hotel-Information) Greater South Side 8.6/10 Excellent (1,740 reviews) "good value and a very good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARK CA $91 CA $102 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Des-Moines-Hotels-Days-Inn-Suites-By-Wyndham-Des-Moines-Airport.h49826.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/2000000/1840000/1836200/1836184/a1ae2959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1840000/1836200/1836184/5f933aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1840000/1836200/1836184/7aea1f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1840000/1836200/1836184/4f9f1eae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drury Inn & Suites West Des Moines [](https://www.expedia.ca/Des-Moines-Hotels-Drury-Inn-Suites-West-Des-Moines.h1836184.Hotel-Information) West Des Moines 9.4/10 Exceptional (1,006 reviews) "A great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $137 CA $153 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Des-Moines-Hotels-Drury-Inn-Suites-West-Des-Moines.h1836184.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/7f5701b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/11bfc987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/ca7fb3d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/70000/64300/64224/bd90e9b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Osceola [](https://www.expedia.ca/Osceola-Hotels-Quality-Inn-Osceola.h64224.Hotel-Information) Osceola 8.6/10 Excellent (66 reviews) "Great place to stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $123 CA $138 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Osceola-Hotels-Quality-Inn-Osceola.h64224.Hotel-Information) ![Gift shop](https://images.trvl-media.com/lodging/122000000/121310000/121306700/121306617/31dbbeb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/122000000/121310000/121306700/121306617/6025de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/122000000/121310000/121306700/121306617/856ef05c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121310000/121306700/121306617/cb59b5fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru By Hilton Norwalk Des Moines [](https://www.expedia.ca/Norwalk-Hotels-Tru-By-Hilton-Norwalk-Des-Moines.h121306617.Hotel-Information) Norwalk 8.0/10 Very good (4 reviews) "This was a very new hotel. The staff was very friendly and welcoming. The rooms were very clean and the the adjoining rooms were perfect size. This hotel provides everything you need for a quick weekend getaway. Great place for families, with a pool table and fun activities to enjoy in the lobby! Room was cleaned every day! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) lamount CA $111 CA $125 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Norwalk-Hotels-Tru-By-Hilton-Norwalk-Des-Moines.h121306617.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/647a39b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/b36bba35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/44fe7428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/12000000/11120000/11110300/11110264/11a27a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Evergreen Inn [](https://www.expedia.ca/Osceola-Hotels-Evergreen-Inn.h11110264.Hotel-Information) Osceola 9.0/10 Wonderful (694 reviews) "The room was very clean and comfortable. Kari was super friendly and helpful as we checked in. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy CA $72 CA $80 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Osceola-Hotels-Evergreen-Inn.h11110264.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=2026-02-10&endDate=2026-02-11®ionId=181516&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winterset Hotel Reviews ![Wildwood Lodge](https://images.trvl-media.com/lodging/8000000/7600000/7599000/7598985/c7d37989_y.jpg) ### Wildwood Lodge 10/10 Excellent "Everything was great. Highly recommend. " [](https://expedia.ca/Des-Moines-Hotels-Wildwood-Lodge.h7598985.Hotel-Information) ![SpringHill Suites Des Moines West](https://images.trvl-media.com/lodging/1000000/560000/554000/553975/2e2cdb05_y.jpg) ### SpringHill Suites Des Moines West 10/10 Excellent "The room was magnificent and huge! The couch super comfy. My mom wanted to stay longer!" [](https://expedia.ca/Des-Moines-Hotels-SpringHill-Suites-Des-Moines-West.h553975.Hotel-Information) ![Hampton Inn Des Moines-Airport](https://images.trvl-media.com/lodging/1000000/20000/17400/17394/11ef309e_y.jpg) ### Hampton Inn Des Moines-Airport 10/10 Excellent "The front desk person on arrival was super helpful and pleasant" [](https://expedia.ca/Des-Moines-Hotels-Hampton-Inn-Des-Moines-Airport.h17394.Hotel-Information) ![Quality Inn & Suites Des Moines Airport](https://images.trvl-media.com/lodging/1000000/20000/18000/17922/063c0fb4_y.jpg) ### Quality Inn & Suites Des Moines Airport 10/10 Excellent "Room was great " [](https://expedia.ca/Des-Moines-Hotels-Quality-Inn-Suites-Des-Moines-Airport.h17922.Hotel-Information) ![Fairfield Inn and Suites by Marriott Des Moines West](https://images.trvl-media.com/lodging/1000000/80000/77600/77590/01d93670_y.jpg) ### Fairfield Inn and Suites by Marriott Des Moines West 10/10 Excellent "Nice staff. clean rooms " [](https://expedia.ca/Des-Moines-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Des-Moines-West.h77590.Hotel-Information) ![Drury Inn & Suites West Des Moines](https://images.trvl-media.com/lodging/2000000/1840000/1836200/1836184/2af2a76d_y.jpg) ### Drury Inn & Suites West Des Moines 10/10 Excellent "Room was clean and staff friendly " [](https://expedia.ca/Des-Moines-Hotels-Drury-Inn-Suites-West-Des-Moines.h1836184.Hotel-Information) ![Baymont by Wyndham Des Moines Airport](https://images.trvl-media.com/lodging/1000000/480000/473200/473122/35b2ee27_y.jpg) ### Baymont by Wyndham Des Moines Airport 10/10 Excellent "Clean room and very friendly staff" [](https://expedia.ca/Des-Moines-Hotels-Baymont-By-Wyndham-Des-Moines-Airport.h473122.Hotel-Information) ![Sonesta Simply Suites Des Moines](https://images.trvl-media.com/lodging/1000000/90000/84500/84463/2f117fac_y.jpg) ### Sonesta Simply Suites Des Moines 10/10 Excellent "All good" [](https://expedia.ca/Des-Moines-Hotels-Sonesta-Simply-Suites-Des-Moines.h84463.Hotel-Information) ![Cobblestone Inn & Suites - Winterset, IA](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/f46e6906_y.jpg) ### Cobblestone Inn & Suites - Winterset, IA 10/10 Excellent "Clean rooms. Friendly staff and easy to find " [](https://expedia.ca/Winterset-Hotels-Cobblestone-Inn-Suites-Winterset.h10446857.Hotel-Information) ## Frequently asked questions ### What can a history enthusiast expect from a trip to Winterset? ### How many historical hotels are there in Winterset? ### What are the most important historical places and other sights to visit in Winterset? ### What is a historic hotel like in Winterset? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Winterset have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Western Skies Scenic Byway ](https://www.expedia.ca/3Star-Western-Skies-Scenic-Byway-Hotels.s30-0-d713341091283341312.Travel-Guide-Filter-Hotels) - [Apartments in Adel ](https://www.expedia.ca/Adel-Apartments.d6343218-aaApartments.Travel-Guide-Accommodation) - [B&B in Adel ](https://www.expedia.ca/Adel-Bed-And-Breakfast.d6343218-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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