Winterset Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

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

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 £112 per night from 11 Jul to 12 Jul
£112
11 Jul - 12 Jul
includes taxes & fees
9.2/10 Wonderful! (763 reviews)
"Orange juice at breakfast would have been nice."

Reviewed on 6 Jul 2026

Cobblestone Inn & Suites - Winterset, IA
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 £85 per night from 8 Jul to 9 Jul
£85
8 Jul - 9 Jul
includes taxes & fees
9/10 Wonderful! (800 reviews)
"The motel is in the process of remodeling. What I saw was very nice. My room was clean and neat. I have worked in the motel business a long time ago and I am critical of a lot of things. This motel filled my needs and will be very nice when complete. I met three members of the staff and they were ..."

Reviewed on 30 Jun 2026

Covered Bridge Inn
Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

3 out of 5
7225 Vista Dr West Des Moines IA
Fully refundableReserve now, pay when you stay
The price is £104 per night from 14 Jul to 15 Jul
£104
14 Jul - 15 Jul
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Property was clean, updated, and staff was very nice."

Reviewed on 6 Jul 2026

Fairfield Inn and Suites by Marriott Des Moines West
See all 561 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Winterset attractions

A red bridge over a calm river with greenery around.

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.
See properties

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.

Explore a world of travel with Expedia

* 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.