Winterset Holidays

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Your Winterset Holiday

There's no better way to get away than with one of our holiday packages to Winterset. The rich history and friendly locals are a couple of the compelling reasons to visit this captivating city. Fill your free time with visits to John Wayne Birthplace Museum, The Winterset Stage and Clark Tower, some of the top attractions you should see during a trip to Winterset. A couple of quick clicks is all it takes to craft the ultimate Winterset holiday on Expedia.

Winterset Holiday

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

Our pick of the best Winterset Hotel Deals

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 AU$103 per night from 30 Mar to 31 Mar
AU$103
includes taxes & fees
30 Mar - 31 Mar
9/10 Wonderful! (657 reviews)
"Enjoyed everything"

Reviewed on 17 Mar. 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 AU$242 per night from 30 Mar to 31 Mar
AU$242
includes taxes & fees
30 Mar - 31 Mar
9.2/10 Wonderful! (613 reviews)
"Love that there was a very large area to walk the dog."

Reviewed on 22 Mar. 2025

Cobblestone Inn & Suites - Winterset, IA
Stoney Creek Hotel Des Moines - Johnston
Stoney Creek Hotel Des Moines - Johnston
2.5 out of 5
5291 Stoney Creek Court, Johnston, IA
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 30 Mar to 31 Mar
AU$175
includes taxes & fees
30 Mar - 31 Mar
8.8/10 Excellent! (1,635 reviews)
"Even though the hotel is a little older, I have always liked staying there. Price wise is good, whether for work conferences or personal business, I have always had a nice stay. Handicap parking is helpful and staff being able for assistance if needed. Doors and the area around the hotel are nicely ..."

Reviewed on 25 Mar. 2025

Stoney Creek Hotel Des Moines - Johnston
See all 517 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

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Winterset holiday package cost?
Offering great value package deals on Expedia, you’ll be pleasantly surprised at how much a holiday to Winterset costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winterset?
You’re likely to find lower rates and greater availability in December, January and February. Explore our cheap Winterset holiday packages and you could land some great off-season discounts.
How many days is enough for Winterset?
The ideal length for your Winterset holiday depends on what you’d like to do and see. Usually, a few days to a week will give you time to visit all the main sights and discover some hidden spots along the way.
Is it worth booking a holiday package to Winterset?
Winterset is a good holiday destination with attractions like The Winterset Stage among the many things to keep you entertained. Whether you’re travelling with the family or getting away with friends, a Winterset holiday promises a good time for everyone.
How to find the best Winterset package deals?
Use Expedia’s filter tool to find some unbeatable Winterset package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your break for midweek, or browse for Winterset package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it’s typically best to book your holiday package well in advance.
Is it cheaper to book a Winterset holiday as a package?
An Expedia holiday package could land you considerable savings when compared to booking flights and stays individually. Better still, you can tailor your Winterset trip to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Winterset?
If you’re considering a spontaneous Winterset trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Winterset?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Winterset.
  2. Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and flights. Your accommodation will likely be the largest expense during your trip to Winterset.
  3. Decide how long to go away for: Now that you’re more familiar with Winterset, you can work out the right length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that’s left now is to choose a Winterset holiday package that brings all your bookings together.

Discover the most popular places to visit in Winterset

Roseman Bridge

Roseman Bridge

You can learn about the history of Winterset when you stop by Roseman Bridge. Make some time to visit the monuments while you're in the area.

Roseman Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.