Winterset Holidays from £954

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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!

Top Winterset Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Harlan Inn and Suites by OYO Harlan

Harlan Inn and Suites by OYO Harlan

2.5 out of 5
Price was £1,061, price is now £954 per person
£954
per person
2 Oct - 9 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Des Moines (DSM)
6.8/10 (106 reviews)
I love my every stay at this hotel

Reviewed on 12 Feb 2025

Cobblestone Inn & Suites - Avoca

Cobblestone Inn & Suites - Avoca

2.5 out of 5
Price was £1,257, price is now £1,165 per person
£1,165
per person
2 Oct - 9 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Des Moines (DSM)
8.6/10 Excellent! (624 reviews)
Easy stay off highway. Beds were comfortable, breakfast was good, staff was friendly. It’s an older hotel and right next to a truck stop, so it’s busy with trucks but it was quiet overnight. Not fancy but decent and good price. Fine for an overnight!

Reviewed on 14 Aug 2025

Baymont by Wyndham Harlan

Baymont by Wyndham Harlan

2.5 out of 5
Price was £1,109, price is now £1,031 per person
£1,031
per person
2 Oct - 9 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Des Moines (DSM)
7.8/10 Good! (357 reviews)
beyond what I expected in small town

Reviewed on 6 Aug 2025

Motel 6 Avoca, IA

Motel 6 Avoca, IA

2 out of 5
Price was £1,077, price is now £1,027 per person
£1,027
per person
2 Oct - 9 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Des Moines (DSM)
8/10 Very Good! (366 reviews)
Best Motel 6 I’ve ever stayed! The wash towels have seen better days. They were clearly brown and gray color. Other than that, great place for the price.

Reviewed on 31 Jul 2025

Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2 out of 5
Price was £1,030, price is now £1,004 per person
£1,004
per person
2 Oct - 9 Oct
found 1 day ago
Return flight included
Manchester (MAN) to Des Moines (DSM)
7.4/10 Good! (296 reviews)
Host was very kind and helpful

Reviewed on 19 Aug 2025

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 £114 per night from 1 Sept to 2 Sept
£114
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (667 reviews)
"Always great!"

Reviewed on 16 Aug 2025

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 £73 per night from 24 Aug to 25 Aug
£73
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (723 reviews)
"Only stayed one night . The beds were comfortable the room was clean and I would definitely stay there again."

Reviewed on 17 Aug 2025

Covered Bridge Inn
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 31 Aug to 1 Sept
£116
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (1,023 reviews)
"Excellent"

Reviewed on 21 Aug 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 529 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

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.