Winterset Vacation Packages 2026

Top Winterset hotels deals

Cobblestone Inn & Suites - Winterset, IA

1304 North 4th Avenue Winterset IA

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$101 total

Jan 2 - Jan 3

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.

Breakfast included

Pet friendly

Covered Bridge Inn

1312 Cedar Bridge Rd. Winterset IA

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$122 total

Jan 2 - Jan 3

Total with taxes and fees

This motel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A terrace, a picnic area, and a computer station are also on offer.

Breakfast included

Pet friendly

Stoney Creek Hotel Des Moines - Johnston

5291 Stoney Creek Court Johnston IA

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$108 total

Jan 30 - Jan 31

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Hotel Fort Des Moines, Curio Collection by Hilton

1000 Walnut St Des Moines IA

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$160 total

Jan 4 - Jan 5

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a business center, and a coffee shop are also offered.

Free WiFi

Restaurant

Fairfield Inn and Suites by Marriott Des Moines West

7225 Vista Dr West Des Moines IA

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$85 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Home2 Suites by Hilton Des Moines at Drake University

2650 University Ave. Des Moines IA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$105 total

Jan 4 - Jan 5

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

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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

#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.

Roseman Bridge

4/5(5 reviews)

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

On a stop over going to Whistler Mountain #blue #wanderwoman #Canada #takemeback

Clark Tower

4/5(4 reviews)

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

John Wayne Birthplace Museum

4.5/5(62 reviews)

You can spend an afternoon browsing the exhibits at John Wayne Birthplace Museum in Winterset. While you're in the area, wander around the natural setting.

Frequently asked questions

How much are vacation packages to Winterset?

Your travel dreams can all come true in Winterset for only . 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.