Winterset Vacations

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  • Better together

    Save up to SAR 5,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Find the Best Winterset Vacation Packages

Winterset Hotel Deals

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 SAR 416 per night from Jun 24 to Jun 25
SAR 416
SAR 466 total
24 Jun - 25 Jun
includes taxes & fees
9.2/10 Wonderful! (744 reviews)
"Great value in this mid west town. Reasonably priced, clean & convenient."

Reviewed on 22 May 2026

Cobblestone Inn & Suites - Winterset, IA
Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd. Winterset IA
The price is SAR 381 per night from Jun 3 to Jun 4
SAR 381
SAR 427 total
3 Jun - 4 Jun
includes taxes & fees
9/10 Wonderful! (791 reviews)
"In the middle of renovations but was hardly noticeable. Everyone was super kind and friendly. Very quiet. Decent breakfast in an out of the way room."

Reviewed on 27 May 2026

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 SAR 539 per night from Jun 21 to Jun 22
SAR 539
SAR 603 total
21 Jun - 22 Jun
includes taxes & fees
9.6/10 Exceptional! (1,159 reviews)
"Luxury! Would stay anytime."

Reviewed on 26 May 2026

Hotel Fort Des Moines, Curio Collection by Hilton
See all 563 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 do I find cheap flights to Winterset that have flexible change policies?
We understand that plans can change from one minute to the next, so choosing a flexible ticket with Expedia makes sense. Simply mark the "No change fee" box directly under the "Flexible change policies" filter. Your low-cost, flexible flight to Winterset is just a few clicks away.
Which airlines fly to Winterset?
Book a seat with one of these airlines and the dynamic region of Winterset will be yours to explore:

  • American Airlines - 407 flights to or near Winterset each month, including 407 flights to Des Moines Intl. Airport (DSM) per month.
  • United Airlines - 294 flights to or near Winterset each month, including 294 flights to Des Moines Intl. Airport (DSM) per month.
  • Delta Air Lines - 229 flights to or near Winterset each month, including 229 flights to Des Moines Intl. Airport (DSM) per month.

How can I find cheap tickets to Winterset?
One of the easiest ways to find cheap tickets to Winterset is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It will reveal the cheapest prices for nearby days. The best price for a flight to Winterset in the last seven days was . Booking well in advance will generally help you score an even better deal.
How much is a flight to Winterset?
There were a lot of cheap fares up for grabs in the last seven days, with the cost of a return airfare to Winterset varying between and . Many lucky travelers scored one-way seats from () for as little as .
What are the most popular airports to fly into in Winterset?
Des Moines Intl. Airport (DSM) is the main entry point for many eager to explore Winterset. Roughly 1,200 flights every month land at this airport.
When is the cheapest time to fly to Winterset?
Take off for Winterset early in the week and you'll usually be rewarded with cheaper fares. Tuesday is generally the cheapest day to hop on a plane, closely followed by Monday. If you're hoping to avoid the priciest flights, give Saturdays a wide berth.
How much is a plane ticket to Winterset?
Plane tickets ranged from just to over the last seven days. When you're ready to book, we'll be ready to help you land an awesome deal to Winterset.
What months are the cheapest to book a flight to Winterset?
February is an excellent month to get your hands on a fantastic deal to Winterset. Bear in mind that the most expensive time to reserve a seat in the States isn't during the peak of summer, but in December.
How long is a flight to Winterset?
It depends on where in the U.S. You're traveling from. These popular domestic routes and their average flight times will give you a rough estimate of how long it'll take you to reach Winterset:

  • Denver, CO (DEN-Denver Intl.) to Des Moines Intl. Airport (DSM) - 1 hour and 42 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Des Moines Intl. Airport (DSM) - 1 hour and 25 minutes
  • Dallas, TX (DFW-Dallas-Fort Worth Intl.) to Des Moines Intl. Airport (DSM) - 1 hour and 54 minutes