Winterset Vacations from $365
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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.
Gateway Hotel and Conference Center at Iowa State University
$579
per person
Nov 13 - Nov 15
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to Des Moines (DSM)
9.2/10 Wonderful! (1,400 reviews)
My check in was the smoothest, greatest check in ever. Stephan was was so kind and made every accommodation I requested. I week stay here again.
Reviewed on Oct 8, 2026
Fairfield Inn & Suites Des Moines Altoona
$473
per person
Nov 13 - Nov 15
found 20 hours ago
Roundtrip flight included
Chicago (ORD) to Des Moines (DSM)
9.4/10 Exceptional! (646 reviews)
It would have been alot better experience but the front desk lady didnt even get out of her chair to help us. She just stayed slouched in her chair the whole transaction.
Reviewed on Oct 4, 2026
Stay near popular Winterset attractions
Roseman Bridge
9.6/10 (75 reviews)
This 1883 wooden bridge gained fame in "The Bridges of Madison County" film with its distinctive flat roof and lattice design. Visit during autumn when vibrant foliage creates a perfect backdrop for photography.
Cedar Bridge
9.8/10 (67 reviews)
Cedar Bridge is the only drivable covered bridge of Madison County, immortalized in the famous novel and film. Drive through this restored 1883 wooden landmark, then enjoy the Victorian gazebos and flower gardens nearby.
Holliwell Bridge
9.6/10 (63 reviews)
The longest covered bridge in Madison County, this historic 1880 structure gained fame in "The Bridges of Madison County." Walk through its timber lattice truss design while enjoying serene views of the Middle River.
John Wayne Birthplace Museum
9.4/10 (131 reviews)
Step into the birthplace of Hollywood legend John Wayne, where personal artifacts and film memorabilia tell his remarkable story. Explore the restored 1907 home and museum exhibits.
Madison County Courthouse
9.4/10 (68 reviews)
Madison County Courthouse is just one of the places to see in Winterset, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the natural setting.
The Winterset Stage
9.0/10 (23 reviews)
This intimate community theater brings professional-quality performances to rural Iowa in a historic setting. Enjoy arts and culture where every seat offers an excellent view of talented local and visiting actors.
Cutler-Donahoe Covered Bridge
This 1871 wooden bridge showcases classic Town lattice truss design, now nestled in Winterset City Park. Walk its 79-foot span and explore the surrounding trails and hedge maze for a peaceful historic experience.
Hogback Bridge
9.4/10 (61 reviews)
Built in 1884, this historic covered bridge features a Town lattice truss design spanning the North River. Stroll through its rustic interior of original wooden planks while admiring the enduring craftsmanship.
Winterset Hotel Deals
Cobblestone Inn & Suites - Winterset, IA
1304 North 4th Avenue Winterset IA
Fully refundableReserve now, pay when you stay
$109 nightly
$122 total
Nov 5 - Nov 6
Total with taxes and fees
9.2/10 Wonderful! (817 reviews)
"Very nice stay. Clean room"
Reviewed on Oct 9, 2026
Covered Bridge Inn
1312 Cedar Bridge Rd. Winterset IA
Fully refundableReserve now, pay when you stay
$106 nightly
$119 total
Oct 12 - Oct 13
Total with taxes and fees
9/10 Wonderful! (819 reviews)
"good"
Reviewed on Oct 1, 2026
Hotel Fort Des Moines, Curio Collection by Hilton
1000 Walnut St Des Moines IA
Fully refundableReserve now, pay when you stay
$126 nightly
$141 total
Nov 8 - Nov 9
Total with taxes and fees
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 |
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Frequently asked questions
How much does a Winterset vacation package cost?
Offering great value package deals from $365 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
