Winterset Vacations from $305

Book a Hotel + Flight or Car together to unlock savings

Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

Your Winterset Vacation

Book a Winterset vacation package and get set for an awesome adventure. Famous for its rich history and friendly locals, there's loads to like about this fascinating city. Every trip to Winterset needs a well-planned itinerary. Fill yours with leading attractions like John Wayne Birthplace Museum, The Winterset Stage and Clark Tower. Stop dreaming and start traveling. Check out the wide range of options on Expedia today and finally put your Winterset vacation plans into motion!

The Latest Winterset vacation packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Des Moines West Clive

La Quinta Inn & Suites by Wyndham Des Moines West Clive

3 out of 5
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Des Moines (DSM)
8.6/10 Excellent! (1,008 reviews)
The staff were kind, welcoming and helpful. The suite was clean and comfortable. There wasn’t a lot of grass to walk the dogs and other patrons didn’t clean up after their dogs.

Reviewed on Jul 6, 2025

Microtel Inn & Suites by Wyndham Ames

Microtel Inn & Suites by Wyndham Ames

2 out of 5
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Des Moines (DSM)
7.8/10 Good! (1,001 reviews)
The property met our needs in Ames. The room was compact, but functional. The price was good.

Reviewed on Jul 2, 2025

La Quinta by Wyndham Altoona Des Moines

La Quinta by Wyndham Altoona Des Moines

3 out of 5
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Des Moines (DSM)
9/10 Wonderful! (1,570 reviews)
Great place to stay. Thus staff was great, the room and lobby was very clean. The morning breakfast was nothing to write home about? But was decent at best. I give this place 4 stars

Reviewed on Jun 25, 2025

AmericInn by Wyndham Ames

AmericInn by Wyndham Ames

2.5 out of 5
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Des Moines (DSM)
8.4/10 Very Good! (1,010 reviews)
Very nice Inn and staff!

Reviewed on Jul 10, 2025

Wyndham Garden Ankeny/Des Moines

Wyndham Garden Ankeny/Des Moines

3 out of 5
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Des Moines (DSM)
6.2/10 (1,003 reviews)
Very nice front desk staff.

Reviewed on Jun 16, 2025

Don't see what you're looking for?
See all available trips from Milton to Winterset
View all trips

Discover the most popular places to visit in Winterset

#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.

Roseman Bridge
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.

Clark Tower

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.

John Wayne Birthplace Museum

Winterset Hotel Deals

Covered Bridge Inn
Covered Bridge Inn
2.5 out of 5
1312 Cedar Bridge Rd., Winterset, IA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Jul 13 to Jul 14
$98 total
Jul 13 - Jul 14
Total includes taxes and fees
9/10 Wonderful! (699 reviews)
"Clean and super friendly staff. When the front desk informed me of the breakfast hours at check in I said I would be leaving very early before breakfast. He said if I got hungry in the night to let him know and he would open the breakfast room so I could have a snack. I thought that was very ..."

Reviewed on Jul 10, 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
$130 nightly
The price is $146 total per night from Jul 13 to Jul 14
$146 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (647 reviews)
"Lovely hotel on the edge of Winterset with large and airy rooms. Staff were friendly and helpful at all times. The constant supply of excellent coffee was great too. Easy parking. Thought it excellent value for money for a woman travelling alone!"

Reviewed on Jul 7, 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
$138 nightly
The price is $154 total per night from Jul 21 to Jul 22
$154 total
Jul 21 - Jul 22
Total includes taxes and fees
9.4/10 Exceptional! (1,018 reviews)
Downtown hotel
"Really nice historic hotel in downtown. Good value for the price. On a quiet street with not much to walk around and do. Carpet was dingy and stained. Housekeeping showed up once the 3 nights we were there to see if we needed anything. It wasn’t explained to us at check in that we wouldn’t get service ..."

Reviewed on Jul 8, 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 518 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.

Find the Best Winterset Vacation Packages

Winterset Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Des Moines Intl. Airport (DSM)
Population
5,200
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Pammel State Park, The Winterset Stage and Roseman Bridge

More vacations you might like

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Winterset vacation package cost?
Offering great value package deals from $305 on Expedia, you'll be pleasantly surprised at how much a vacation to Winterset costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winterset?
If you're looking to score a cheap Winterset vacation package, consider planning a trip in November, December and January. You're likely to find lower prices on flights and accommodations during these quieter months --- perfect for a budget-friendly break.
How many days is enough for Winterset?
With a well-organized travel plan, you can easily hit the top Winterset attractions in a handful of days. But if you want to discover hidden gems or go on day trips, consider booking your Winterset vacation for longer.
Is it worth booking a vacation package to Winterset?
Winterset has everything you need for a wonderful getaway. Begin your Winterset vacation on a high note by checking out popular attractions like The Winterset Stage.
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 vacation package well in advance.
Is it cheaper to book a Winterset vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Winterset vacation packages?
Your Winterset trip should be an escape from your daily routine, not a reason for money-related stress. So to allow you extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.