Winterset Vacations from $594
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Stoney Creek Hotel Des Moines - Johnston
$634
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Austin (AUS) to Des Moines (DSM)
8.8/10 Excellent! (1,910 reviews)
Room was clean. Breakfast included bacon. Coffee is not very good. Need to use Bunn coffee makers for breakfast
Reviewed on Oct 11, 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
$105 nightly
$118 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (818 reviews)
"This was my very first visit to Winterset. Very friendly community. The hotel is VERY NICE. Staff was very welcoming and helpful. I'm already planning a return visit."
Reviewed on Oct 11, 2026
Covered Bridge Inn
1312 Cedar Bridge Rd. Winterset IA
Fully refundableReserve now, pay when you stay
$104 nightly
$116 total
Oct 18 - Oct 19
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
9.6/10 Exceptional! (1,368 reviews)
"clean rooms good location friendly staff"
Reviewed on Oct 12, 2026
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
Frequently asked questions
How much does a Winterset vacation package cost?
Offering great value package deals from $594 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.
Explore a world of travel with Expedia
- Hotels in Saint Charles
- Cabins in Winterset
- Motels in Winterset
- Pet Friendly in Winterset
- Best Western Hotels in Winterset
- 4 Star Hotels in West Des Moines
- Hotels in De Soto
- Romantic in Winterset
- Motel 6 Hotels in Winterset
- Hotels in Waukee
- 3 Star Hotels in Winterset
- Hotels in Winterset
- Hotels in Adel
- Hotels in Norwalk
- Flights to Winterset
- United Airlines Denver (DEN) to Des Moines (DSM) flights
- Flights to West Des Moines
- Flights to Saint Charles
- Delta Air Lines Atlanta (ATL) to Des Moines (DSM) flights
- Flights to Stuart
- Flights to Des Moines
- Flights from Chicago (ORD) to Des Moines (DSM)
- Flights to Waukee
- Flights from Denver (DEN) to Des Moines (DSM)
- Central Iowa All Inclusive Vacation Packages
- Central Iowa All Inclusive Vacation Packages
- Where to stay in Grimes
- Visit Van Meter
- Where to stay in Perry
- Central Iowa All Inclusive Vacation Packages
- Central Iowa All Inclusive Vacation Packages
- Where to stay in Winterset
- Greater Des Moines Botanical
- Central Iowa All Inclusive Vacation Packages
- Central Iowa All Inclusive Vacation Packages
- Visit Court District
- Where to stay in Altoona
- Creston Vacations
- Visit Waukee
- Central Iowa All Inclusive Vacation Packages
- Central Iowa All Inclusive Vacation Packages
- Waukee Vacations
- Where to stay in Des Moines
- Visit Des Moines
- Knoxville Vacations
- Visit West Des Moines
- Val Air Ballroom
- Visit New Virginia
- Central Iowa All Inclusive Vacation Packages
- Visit Chariton
- Visit Downtown Des Moines
- Visit Osceola
- Visit Lovington
- Where to stay in Urbandale
- Where to stay in Knoxville
- Where to stay in Indianola
- Visit Ankeny
- John Wayne Birthplace Museum
- Visit Historic East Village
- Where to stay in Central Iowa
- Central Iowa All Inclusive Vacation Packages
- Roseman Bridge
- Norwalk Vacations
- Atlantic Vacations
- Cumming Vacations
- Downtown Des Moines Vacations
- Central Iowa All Inclusive Vacation Packages
- Central Iowa All Inclusive Vacation Packages
- Johnston Vacations
- Des Moines Vacations
- Visit Winterset
- Central Iowa All Inclusive Vacation Packages
- Where to stay in Clive
- West Des Moines Vacations
- Where to stay in Creston
- National Balloon Museum
- Where to stay in Pella
- Visit Stuart
- Budget Rental Cars in Winterset
- Car rentals in Truro
- Car rentals in Waukee
- Car rentals in Winterset
- Van Car Rentals in West Des Moines
- Car rentals in De Soto
- Minivan Car Rentals in Des Moines Intl.
- Car rentals in Norwalk
- Enterprise Rental Cars in Winterset
- Car rentals in West Des Moines
- SUV Car Rentals in Des Moines Intl.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
