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

Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd., Winterset, IA
Fully refundableReserve now, pay when you stay
The price is £73 per night from 10 Aug to 11 Aug
£73
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (714 reviews)
"The workers were so kind and helpful! We were there for a music festival so they were booked up, but when we called and requested an earlier checkin time they were flexible and made it happen for us! The staff are very accommodating and you can tell that they want their guests to be comfortable and ..."

Reviewed on 4 Aug 2025

Covered Bridge Inn
Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
1304 North 4th Avenue, Winterset, IA
Fully refundableReserve now, pay when you stay
The price is £102 per night from 18 Aug to 19 Aug
£102
18 Aug - 19 Aug
includes taxes & fees
9.2/10 Wonderful! (657 reviews)
"Excellent value and convenient to spots of interest"

Reviewed on 1 Aug 2025

Cobblestone Inn & Suites - Winterset, IA
Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
1000 Walnut St, Des Moines, IA
Fully refundableReserve now, pay when you stay
The price is £116 per night from 17 Aug to 18 Aug
£116
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"Can’t say enough about the dining options on property. The café coffee is some of the best I’ve ever had. The mac & cheese there is to die for. And the daily happy hour at the upscale restaurant was also amazing. Staff was amazing and I certainly will never stay anywhere else in Iowa."

Reviewed on 6 Aug 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 532 properties in Winterset
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.
All Inclusive Holidays
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

Popular places to visit

John Wayne Birthplace Museum

You can spend an afternoon studying the exhibits at John Wayne Birthplace Museum in Winterset. While you're in the area, wander around the natural setting.

John Wayne Birthplace Museum

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.

* 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.