Winterset Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

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 2.325.659 ₫ per night from 23 Jun to 24 Jun
2.325.659 ₫
2.558.225 ₫ total
23 Jun - 24 Jun
includes taxes & fees
9/10 Wonderful! (688 reviews)
"We found the Covered Bridge Inn to be perfect for our needs. The Owner was very accommodating. My husband is unable to carry/lift things so the Owner came out and helped me bring in our luggage. He was very pleasant, recommended places to eat and things to see. Great stay, would recommend."

Reviewed on 17 Jun 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 3.597.977 ₫ per night from 23 Jun to 24 Jun
3.597.977 ₫
4.029.661 ₫ total
23 Jun - 24 Jun
includes taxes & fees
9.2/10 Wonderful! (633 reviews)
"Cobblestone Inn was in a great location for visiting places near Winterset, IA. The hotel rooms are very clean. The breakfast was nicely done. Staff is very helpful."

Reviewed on 16 Jun 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 3.178.445 ₫ per night from 29 Jun to 30 Jun
3.178.445 ₫
3.559.858 ₫ total
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"No complaints"

Reviewed on 16 Jun 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 514 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.

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.

Popular places to visit

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
Clark Tower

Clark Tower

You can find out about the history of Winterset with a trip to Clark Tower. Make some time to visit the shops while you're in the area.

Clark Tower

John Wayne Birthplace Museum

4/5(1 review)

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