Title: Winterset Vacation Packages 2026 from $639 | 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 $639 ## 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/1000000/20000/18900/18835/56a1214f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Downtown - Mercy Area by IHG Downtown Des Moines $639 per person Jun 18 - Jun 22 found 17 hours ago Roundtrip non-stop flight included Boston (BOS) to Des Moines (DSM) 7.8/10 Good! (1,006 reviews) I loved the pool, It was 8-9 feet. Which is very fun to swim in. The rooms were spacious and everything was neat and comfortable. We didn't really talk with staff but they seemed nice as we were checking-in. Reviewed on Mar 25, 2026 ![Hyatt Place West Des Moines Jordan Creek](https://images.trvl-media.com/lodging/17000000/16120000/16112600/16112546/018a0ab2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place West Des Moines Jordan Creek $750 per person Jun 18 - Jun 22 found 17 hours ago Roundtrip non-stop flight included Boston (BOS) to Des Moines (DSM) 9.2/10 Wonderful! (1,021 reviews) Clean room, pool was nice, plenty parking. Reviewed on Mar 22, 2026 ![Hilton Des Moines Downtown](https://images.trvl-media.com/lodging/22000000/21330000/21321600/21321542/3d4c6021_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Des Moines Downtown Downtown Des Moines $869 per person Jun 18 - Jun 22 found 17 hours ago Roundtrip non-stop flight included Boston (BOS) to Des Moines (DSM) 9/10 Wonderful! (999 reviews) A front receptionist was repeatedly rude to the customers she managed over the phone. She was argumentative and denigrated her customers on the phone….including me. She argued with how I made my reservation - a phone call to Hilton reservations- she stated was made through a third party. That sort of rudeness required a re-think of her people-facing role. She became frustrated, her voices was raised, argumentative and simply rude. Never should she have access to customers. Reviewed on Mar 26, 2026 ![Hampton Inn Des Moines-Airport](https://images.trvl-media.com/lodging/1000000/20000/17400/17394/9e02de50_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn Des Moines-Airport Greater South Side $799 per person Jun 18 - Jun 22 found 17 hours ago Roundtrip non-stop flight included Boston (BOS) to Des Moines (DSM) 8.8/10 Excellent! (1,007 reviews) Shuttle at front door. Reviewed on Mar 23, 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 $733 per person Jun 18 - Jun 22 found 17 hours ago Roundtrip non-stop flight included Boston (BOS) to Des Moines (DSM) 9.4/10 Exceptional! (1,011 reviews) You really can’t go wrong booking with this hotel. Overall, everything about this location was top-tier, and I will definitely be booking again soon. Out of the three customer service representatives at the front desk, two of them were absolutely phenomenal. Both were gentlemen—one working the evening shift and the other on the day shift when we checked out. When I say their service was outstanding, I truly mean it. In the room we booked, I did assume there would be a stovetop rather than a portable cooktop, but it wasn’t a major issue. However, there was one young lady whose customer service didn’t quite match the high standard set by the others. She didn’t seem very engaged, and her attitude felt out of place compared to the excellent service we received from the rest of the staff Reviewed on Mar 23, 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=DSM&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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 4/5(5 reviews) 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) ![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 4.5/5(6 reviews) 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.com/Holliwell-Bridge-Winterset.d6105998.Vacation-Attraction) ![Clark Tower](https://images.trvl-media.com/place/181516/baa8c8c4-f22a-403f-ac61-135bce9a9e0d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Clark Tower 4/5(4 reviews) 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) ## Winterset Hotel Deals ![Cobblestone Inn & Suites - Winterset, IA](https://images.trvl-media.com/lodging/11000000/10450000/10446900/10446857/221411cd_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 $107 nightly $120 total Mar 31 - Apr 1 Total with taxes and fees 9.2/10 Wonderful! (724 reviews) The breakfast would have been good had it not been for the awful eggs. They were dry and inedible. Otherwise, the hotel was clean and efficient for a one night stay. Reviewed on Mar 29, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=10446857&PinnedHotelID=10446857&HadPinnedHotel=true®ionId=181516) ![Covered Bridge Inn](https://images.trvl-media.com/lodging/1000000/440000/440000/439956/cf139e75_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Covered Bridge Inn 1312 Cedar Bridge Rd. Winterset IA Fully refundableReserve now, pay when you stay $79 nightly $88 total Apr 5 - Apr 6 Total with taxes and fees 9/10 Wonderful! (783 reviews) New management, doing excellent so far! There are big renovation plans in the future, excited to see how it turns out. Reviewed on Mar 28, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=439956&PinnedHotelID=439956&HadPinnedHotel=true®ionId=181516) ![Modern home on acreage with pond, trails, rolling hills, and sunset views](https://images.trvl-media.com/lodging/124000000/123350000/123347300/123347234/ec72ec44_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Modern home on acreage with pond, trails, rolling hills, and sunset views Winterset IA [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F13%2F2026&endDate=4%2F14%2F2026&selected=123347234&PinnedHotelID=123347234&HadPinnedHotel=true®ionId=181516) [](https://expedia.com/Hotel-Search?startDate=4%2F13%2F2026&endDate=4%2F14%2F2026&selected=123347234&PinnedHotelID=123347234&HadPinnedHotel=true®ionId=181516) [See all 563 properties in Winterset](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F31%2F2026&endDate=4%2F1%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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### 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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