Winterset Holidays
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Your Winterset Holiday
Book a Winterset holiday 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, The Winterset Stage and Clark Tower. Stop dreaming and start travelling. Check out the wide range of options on Expedia today and finally put your Winterset holiday plans into motion!
Winterset Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Des Moines Intl. Airport (DSM) |
Population | 5,200 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | The Winterset Stage, Pammel State Park and Roseman Bridge |
Top hotels in Winterset
Cobblestone Inn & Suites - Winterset, IA
1304 North 4th Avenue Winterset IA
Fully refundableReserve now, pay when you stay
£112
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (792 reviews)
"Great place to stay"
Reviewed on 21 Aug 2026
Covered Bridge Inn
1312 Cedar Bridge Rd. Winterset IA
Fully refundableReserve now, pay when you stay
£83
22 Aug - 23 Aug
includes taxes & fees
9/10 Wonderful! (809 reviews)
"The staff was wonderful and it was clean"
Reviewed on 21 Aug 2026
Fairfield Inn and Suites by Marriott Des Moines West
7225 Vista Dr West Des Moines IA
Fully refundableReserve now, pay when you stay
£81
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Nice rooms, equipped with refrigerator and coffee maker. Bathroom large and easy to navigate. Breakfast was abundant and delicious. Lovely staff"
Reviewed on 20 Aug 2026
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.
Stay near popular Winterset attractions
Roseman Bridge
9.6/10 (75 reviews)
This 1883 wooden bridge gained fame in "The Bridges of Madison County" film with its distinctive flat roof and lattice design. Visit during autumn when vibrant foliage creates a perfect backdrop for photography.
Cedar Bridge
9.8/10 (67 reviews)
Cedar Bridge is the only drivable covered bridge of Madison County, immortalised in the famous novel and film. Drive through this restored 1883 wooden landmark, then enjoy the Victorian gazebos and flower gardens nearby.
Holliwell Bridge
9.6/10 (63 reviews)
The longest covered bridge in Madison County, this historic 1880 structure gained fame in "The Bridges of Madison County." Walk through its timber lattice truss design while enjoying serene views of the Middle River.
John Wayne Birthplace Museum
9.4/10 (131 reviews)
Step into the birthplace of Hollywood legend John Wayne, where personal artefacts and film memorabilia tell his remarkable storey. Explore the restored 1907 home and museum exhibits.
Madison County Courthouse
9.4/10 (68 reviews)
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.
Cutler-Donahoe Covered Bridge
This 1871 wooden bridge showcases classic Town lattice truss design, now nestled in Winterset City Park. Walk its 79-foot span and explore the surrounding trails and hedge maze for a peaceful historic experience.
The Winterset Stage
9.0/10 (23 reviews)
This intimate community theatre brings professional-quality performances to rural Iowa in a historic setting. Enjoy arts and culture where every seat offers an excellent view of talented local and visiting actors.
Hogback Bridge
9.4/10 (61 reviews)
Built in 1884, this historic covered bridge features a Town lattice truss design spanning the North River. Stroll through its rustic interior of original wooden planks while admiring the enduring craftsmanship.
Frequently asked questions
Why should I book my Winterset holiday with Expedia?
Choose Expedia to organise your next adventure with ease, all in one place. Our insider tip for bagging a fabulous deal on a Winterset retreat? Bundle your hotel, flights and/or hire car into a package holiday. Then add a few fun tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to panic if you have to switch up your travel plans. Round-the-clock assistance with making tweaks to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Winterset?
If you'd like to experience the excitement of Winterset during the high season, plan your escape for February, April and June. November, December and January are usually the quietest months of the year. Arrange your visit to Winterset based on what kind of adventure you're looking for. January is the coolest month, when daytime temperatures average -5ºC. In July, the warmest month, you'll experience temperatures of around 23ºC during the day.
What is the top hotel for my holiday in Winterset?
Offering plenty of amenities and a cosy place to relax between adventures, Cobblestone Inn & Suites - Winterset, IA will make the perfect base for your Winterset holiday.
How do I get a cheap holiday to Winterset?
Bundle your hotel and flight bookings, toss in extras such as activities or a hire car, and save with a Winterset holiday. You won't just walk away with awesome discounts on your adventure — you'll have a world of choice too. When you book with Expedia, you can choose from more than 400 airlines and 321,000 properties globally. Your next epic adventure begins right here, right now! Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Winterset holiday?
With must-see tourist attractions like John Wayne Birthplace Museum and Roseman Bridge, a holiday in Winterset promises plenty of exciting places to visit. The Winterset Stage and Clark Tower are two other sights also worth checking out.
What is the best area to stay in when on holiday in Winterset?
Winterset has plenty of interesting places to see, like John Wayne Birthplace Museum. Book accommodation near this attraction and make sightseeing a breeze.
Do I need a visa for my Winterset holiday?
Visa requirements for Winterset vary depending on your nationality and reason for your visit. It's best to check official government websites to determine if you need a visa for your trip. Here you'll also find the most up-to-date information, including details about application procedures or supporting documentation you might need. Research your visa requirements well ahead of time to ensure a hassle-free travel experience. Finally, make sure your passport is valid for at least six months from your return date.
What should I wear on my Winterset holiday?
Consider the type of activities planned during your Winterset trip and bring versatile pieces that you can mix and match. For fashion inspiration or even information on dress codes, browse a few style blogs or social media accounts. Pack your bags with confidence by monitoring the weather forecast in Winterset. July brings the warmest temperatures, with daytime averages of 23ºC, while January days average -5ºC, making it the coolest time of year.
What does an Expedia Winterset holiday include?
That depends on what sort of trip you're contemplating. Winterset holiday deals can include flights, hotels and car hires. You can mix and match to find the bundle that fits your needs. You can also add on experiences and activities after you've booked to land even bigger discounts. Explore an excellent range of property types and choose one that suits your group size. The most in-demand rentals here are private holiday homes and agritourism properties. With Expedia, it's a breeze to tailor your Winterset escape the way you like.
Does Expedia offer Book Now, Pay Later Winterset holidays?
Expedia has teamed up with online lender Klarna to make your next break easier on your wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that falls within your budget. Browse these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams possible.
- No-deposit holidays: Clicking the "book now" button is much easier with this option. With no upfront fee for your escape, you can Book Now, Pay Later and start working on your travel plans.
Can I choose my airline with a Winterset Expedia holiday?
Yes — that's the beauty of an Expedia package. You're the boss! We have access to more than 400 airline partners throughout the world, so you have options galore when putting together your Winterset getaway.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
