Title: Secure Best Winterset Vacation Packages 2026 | Expedia.com [Winterset Travel Guide](https://expedia.com/Winterset.dx181516)[Hotels in Winterset](https://expedia.com/Winterset-Hotels.d181516.Travel-Guide-Hotels)[Vacation Rentals in Winterset](https://expedia.com/Winterset-Vacation-Rentals.d181516.Travel-Guide-VacationRentals)[Flights to Winterset](https://expedia.com/Cheap-Flights-To-Winterset.d181516.Travel-Guide-Flights)[Car Rentals in Winterset](https://expedia.com/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 Vacations from $393 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/John-Wayne-Birthplace-Museum-Winterset.d6105996.Vacation-Attraction), [The Winterset Stage](https://www.expedia.com/The-Winterset-Stage-Winterset.d553248621561929561.Vacation-Attraction) and [Clark Tower](https://www.expedia.com/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! ## The Latest Winterset vacation packages Price found within the past 48 hours. Click for updated prices. ![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 $393 per person Apr 1 - Apr 5 found 14 hours ago Roundtrip non-stop flight included Houston (HOU) 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 $457 per person Apr 1 - Apr 5 found 14 hours ago Roundtrip non-stop flight included Houston (HOU) to Des Moines (DSM) 9.2/10 Wonderful! (1,004 reviews) Tv to stream wasnt working. Everything else was great. Reviewed on Feb 11, 2026 ![Comfort Inn & Suites Event Center](https://images.trvl-media.com/lodging/1000000/10000/8300/8217/a41cce84_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn & Suites Event Center Downtown Des Moines $468 per person Apr 1 - Apr 5 found 14 hours ago Roundtrip non-stop flight included Houston (HOU) to Des Moines (DSM) 8.8/10 Excellent! (1,003 reviews) Nice clean rooms with great parking and good breakfast. Easily located downtown Reviewed on Jan 25, 2026 ![Fairfield Inn & Suites by Marriott Des Moines Airport](https://images.trvl-media.com/lodging/3000000/2160000/2154400/2154341/46b41a3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairfield Inn & Suites by Marriott Des Moines Airport $420 per person Apr 1 - Apr 5 found 14 hours ago Roundtrip non-stop flight included Houston (HOU) to Des Moines (DSM) 9.2/10 Wonderful! (609 reviews) always stay here. love it Reviewed on Feb 9, 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 $507 per person Apr 1 - Apr 5 found 14 hours ago Roundtrip non-stop flight included Houston (HOU) to Des Moines (DSM) 9/10 Wonderful! (1,000 reviews) Clean room. Friendly staff. Reviewed on Feb 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Winterset [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-13/2026-03-20/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=DSM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](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.com/deals?rfrr=PKG_SPRING_PROMO_181516) ### Discover the most popular places to visit in Winterset ![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.com/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.com/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.com/Cedar-Bridge-Winterset.d6106000.Vacation-Attraction) ## 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 $96 nightly $108 total Mar 3 - Mar 4 Total with taxes and fees 9.2/10 Wonderful! (716 reviews) Clean rooms. Friendly staff and easy to find Reviewed on Jan 18, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%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 $134 nightly $151 total Feb 25 - Feb 26 Total with taxes and fees 9.4/10 Exceptional! (1,083 reviews) The room was very clean Reviewed on Feb 5, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F25%2F2026&endDate=2%2F26%2F2026&selected=9375&PinnedHotelID=9375&HadPinnedHotel=true®ionId=181516) ![Sonesta Simply Suites Des Moines](https://images.trvl-media.com/lodging/1000000/90000/84500/84463/2f117fac_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta Simply Suites Des Moines 7625 Office Plaza Dr N West Des Moines IA Fully refundableReserve now, pay when you stay $71 nightly $80 total Feb 15 - Feb 16 Total with taxes and fees 8.2/10 Very Good! (979 reviews) Good everything Reviewed on Feb 11, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=84463&PinnedHotelID=84463&HadPinnedHotel=true®ionId=181516) [See all 560 properties in Winterset](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F14%2F2026&endDate=2%2F15%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. ## Find the Best Winterset Vacation Packages ## Winterset Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | U.S dollars | | Closest Airport | Des Moines Intl. Airport (DSM) | | Population | 5,200 | | Max Temp Winter | 30ºF | | Max Temp Summer | 80ºF | | Top Sights | [Pammel State Park](https://www.expedia.com/Pammel-State-Park-Winterset.d553248621532648991.Vacation-Attraction), [The Winterset Stage](https://www.expedia.com/The-Winterset-Stage-Winterset.d553248621561929561.Vacation-Attraction) and [Roseman Bridge](https://www.expedia.com/Roseman-Bridge-Winterset.d6106002.Vacation-Attraction) | ## More vacations you might like ![](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.com/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 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations 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### How many days is enough for Winterset? ### Is it worth booking a vacation package to Winterset? ### How to find the best Winterset package deals? ### Is it cheaper to book a Winterset vacation as a package? ### When to book a vacation package to Winterset? ### Does Expedia offer Book Now, Pay Later Winterset vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Madison County Hotels ](https://www.expedia.com/Destinations-In-Madison-County.d553248635976430525.Hotel-Destinations) - [Hotels near John Wayne Birthplace Museum ](https://www.expedia.com/John-Wayne-Birthplace-Museum-Hotels.0-l6105996-0.Travel-Guide-Filter-Hotels) - [Hotels near Madison County Courthouse ](https://www.expedia.com/Madison-County-Courthouse-Hotels.0-l6106008-0.Travel-Guide-Filter-Hotels) - [Hotels near Clark Tower ](https://www.expedia.com/Clark-Tower-Hotels.0-l553248621564886258-0.Travel-Guide-Filter-Hotels) - [Hotels near The Winterset Stage 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