Deals on vacations and trips to Winterset

Save when you book Winterset package deals

Choose two or more items and save on your trip:

Winterset flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Cobblestone Inn & Suites - Winterset, IA
Hotel Fort Des Moines, Curio Collection by Hilton
Wildwood Lodge
Kasa Downtown Des Moines
Hyatt Place West Des Moines Jordan Creek

Top Winterset hotels deals

Don't see what you're looking for?
See all available properties in Winterset
View all properties
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.

Popular places to visit

Frequently asked questions

How much are vacation packages to Winterset?
Your travel dreams can all come true in Winterset for only $539. Packages include flights and hotels, so organizing everything should be a cinch. The only thing you'll need to worry about is what amazing attraction you'll head to first.
How long should my Winterset vacation be?
Many people book a hotel for 2 nights in Winterset. But that doesn't mean you're limited to that. How long you hang around comes down to what you want to do during your vacation. If you'd love to discover every part of this impressive place, treat yourself to another couple of nights (or even an extra week!).
Where can I get the best vacation package deals for Winterset?
You can score awesome Winterset package deals with Travelocity. Pick from 400 airlines and 1,000,000 worldwide properties and turn those vacation daydreams into reality.
Why should I purchase my Winterset vacation bundle with Travelocity?
From our 24/7 customer support to our range of fantastic destinations, we're dedicated to fulfilling your travel dreams. All you need to do is to click and book — our Price Match Guarantee will make sure you score the best price.
Will I save money on my Winterset car rental if I book it with my hotel or flight?
You sure can — combine your hotel, car and flight into a Winterset vacation package and you can save plenty. With so much to see and do in and around Winterset, having your own wheels will make exploring a joy. Once you've buckled yourself in, turn up the tunes and make tracks to Adventureland, a well-known attraction roughly 35 mi from Winterset.
Which airport is best for Winterset?
You'll find Des Moines Intl. Airport (DSM) 25 mi northeast of the center of Winterset.
What is there to do in Winterset?
Winterset is overflowing with places to discover, such as The Winterset Stage and Clark Tower. These two popular attractions are on most tourists' itineraries.
Where should I stay when visiting Winterset?
If you're after someplace comfortable to base yourself, consider the Covered Bridge Inn. It's the top pick for many travelers.

Photos of local treasures

Browse Winterset vacation photos for more inspiration

hogback covered bridge, summer
hogback covered bridge, summer
Hogback Bridge over North River - Winterset, Iowa
Hogback Bridge, Covered Bridges Scenic Byway, Iowa
#adventure
Built in 1883 by Harvey P. Jones and George K. Foster, Roseman is 107 feet in length and sits in its original location. It was renovated in 1992 at a cost of $152,515. In Robert James Waller’s novel, The Bridges of Madison County, and the movie of the same name, Roseman is the bridge Robert Kincaid seeks when he stops at Francesca Johnson’s home for directions. It is also where Francesca leaves her note inviting him to dinner.

Also known as the “haunted” bridge, Roseman is where two sheriff’s posses trapped a county jail escapee in 1892. It is said the man rose up straight through the roof of the bridge, uttering a wild cry, and disappeared. He was never found, and it was decided that anyone capable of such a feat must be innocent.

Explore More Ways to Travel with Travelocity