Cheap Flights to Winterset from $39

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How Much Does it Cost To Fly To Winterset?

The cheapest prices found with in the last 7 days for return flights were $80 and $39 for one-way flights to Winterset for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Oct 30 - Mon, Nov 2
BNA
Nashville Intl.
DSM
Des Moines Intl.
$80 Roundtrip, found 6 days ago
$80
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Oct 30 from Nashville Intl. to Des Moines Intl., returning Mon, Nov 2, priced at $80 found 6 days ago
OriginDestinationTravel DatesFlights From*
DENDes MoinesOctober 1 to October 5$96
BOSDes MoinesNovember 6 to November 9$105
EWRDes MoinesNovember 20 to November 23$114
AZADes MoinesSeptember 16 to September 19$116
LAXDes MoinesOctober 14 to October 19$158
DFWDes MoinesOctober 30 to November 2$193
CLTDes MoinesAugust 24 to August 26$210
ORDDes MoinesOctober 14 to October 15$215
SEADes MoinesOctober 22 to October 27$249
ATLDes MoinesSeptember 5 to September 8$281
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DFWDes MoinesAugust 21 to August 24$211
BOSDes MoinesAugust 21 to August 24$255
LAXDes MoinesAugust 21 to August 28$328
AZADes MoinesAugust 21 to August 24$405
EWRDes MoinesAugust 22 to August 25$423
RFDDes MoinesAugust 23 to August 24$428
CLTDes MoinesAugust 22 to August 26$461
DENDes MoinesAugust 23 to August 28$465
SEADes MoinesAugust 23 to August 30$628
*Prices include taxes and fees

Winterset Flight Information

Traveling to
Winterset
Lowest Price
$80
Number of Airlines Serving
Airlines Serving
Frontier Airlines, Allegiant Air
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Luxury Hotels in Winterset

Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd. Winterset IA
$113 nightly
The price is $126 total per night from Aug 17 to Aug 18
$126 total
Aug 17 - Aug 18
Total with taxes and fees
Stay at this motel in Winterset. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9/10 Wonderful! (807 reviews)
"Although undergoing renovations, this hotel was immaculately clean, quiet, restful, and downright pleasant."

Reviewed on Aug 14, 2026

Opens in a new windowCovered Bridge Inn
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.

Family Friendly Hotels in Winterset

Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd. Winterset IA
$113 nightly
The price is $126 total per night from Aug 17 to Aug 18
$126 total
Aug 17 - Aug 18
Total with taxes and fees
Stay at this motel in Winterset. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9/10 Wonderful! (807 reviews)
"Although undergoing renovations, this hotel was immaculately clean, quiet, restful, and downright pleasant."

Reviewed on Aug 14, 2026

Opens in a new windowCovered Bridge Inn
Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
1304 North 4th Avenue Winterset IA
$151 nightly
The price is $170 total per night from Aug 18 to Aug 19
$170 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Winterset. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (788 reviews)
"Really nice property, especially for a small town. Breakfast was very good as well. We were very impressed with our stay. I would definitely stay there again!"

Reviewed on Aug 15, 2026

Opens in a new windowCobblestone Inn & Suites - Winterset, IA
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.

Need a Car For After Your Flight?

Compact

  • 5 people
  • Unlimited mileage
Des Moines, Iowa, USA

$47

$132 total
found 2 days ago
Compact undefined

Economy

  • 4 people
  • Unlimited mileage
Des Moines, Iowa, USA

$47

$132 total
found 2 days ago
Economy undefined

Midsize

  • 5 people
  • Unlimited mileage
Des Moines, Iowa, USA

$48

$135 total
found 2 days ago
Midsize undefined

Special

  • 4 people
  • Unlimited mileage
Des Moines, Iowa, USA

$49

$147 total
found 2 days ago
Special undefined
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Which airlines fly to Winterset?
Chosen the dates for your big adventure to Winterset? With 6 air companies servicing this city, you're sure to find a flight that fits with your travel plans. These are a few of the most popular carriers:

  • American Airlines
  • Delta Air Lines
  • United Airlines

What airport is best to fly into Winterset?
Traveling to and from Winterset is a cinch, as it's serviced by just one airport. You'll find DSM approximately 25 mi from the bustling downtown area.
Where to stay in Winterset
Winterset isn't exactly known for its extensive variety of accommodations. All the same, with 4 properties on offer via Travelocity, you should be able to find someplace cozy pretty easily. Book a room now to avoid missing out!Looking for someplace to stay in Winterset? The Historic In - Town Acreage Close To All Local Attractions and the Cobblestone Inn & Suites - Winterset, IA are our top properties in this area.
Places to visit in Winterset
If you can't make it to the more popular museums, grow your knowledge at John Wayne Birthplace Museum. Like some more options? Experience an evening of entertainment and talent by visiting The Winterset Stage. But there's more. Search for wildlife, test your photography skills and walk along the trails at Pammel State Park.
How to get through airport security fast when traveling to Winterset
Your adventure to Winterset kicks off as soon as you've satisfied the security checks. We've summarized a few hints and tips to help you get through quickly:

  • Keep your travel ID and boarding pass in an easily accessible place. They'll be the first things you'll be asked for by airport security.
  • You'll need to stop the tunes for a few minutes. Headphones must be taken off and put in a tub to be X-rayed. The same applies to items such as keys and coins.
  • Electronics such as laptops, tablets and phones are always sent through the X-ray machine separately. Be sure to have them within easy reach.
  • Lip balm, toothpaste and other toiletry items in gel, liquid or cream form need to be stored in containers no larger than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock bag.
  • Security personnel may ask you to remove your shoes prior to entering the body scanner. Pick a pair that you can slip off easily. There's nothing more irritating than having to do up your laces again and again.
  • Some destinations have strict biosecurity laws. Think about where you're going to and whether or not you're permitted to fly with fruit and meats.

Plane Tickets To Winterset

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winterset. Browse through our inventory to explore a wide range of cheap flights to Winterset to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winterset as you anxiously await to exit the plane and explore what Winterset has to offer. Considering all the amazing local food and culture in Winterset, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winterset to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winterset without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winterset with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winterset today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.