Madison County Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Madison County
Hotel Fort Des Moines, Curio Collection by Hilton
1000 Walnut St Des Moines IA
Fully refundableReserve now, pay when you stay
S$181
11 Oct - 12 Oct
includes taxes & fees
Stoney Creek Hotel Des Moines - Johnston
5291 Stoney Creek Court Johnston IA
Fully refundableReserve now, pay when you stay
S$139
14 Sept - 15 Sept
includes taxes & fees
8.8/10 Excellent! (1,892 reviews)
"We loved our stay here. A great location. Close to everything we needed. Clean room. Comfortable bed. Great value for the price. Highly recommend and I will stay again!"
Reviewed on 12 Sept, 2026
Days Inn & Suites by Wyndham Des Moines Airport
1901 Hackley Ave Des Moines IA
Fully refundableReserve now, pay when you stay
S$100
22 Sept - 23 Sept
includes taxes & fees
8.6/10 Excellent! (1,815 reviews)
"Overall the room was clean and comfy. Beds and pillows were comfortable. The room did feel damp and smelled a bit musty. Was ok for a one night stop on a road trip."
Reviewed on 11 Sept, 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.
Frequently asked questions
How much does a Madison County holiday package cost?
We make it simple for everyone to travel, with Madison County packages starting from as little as . You'll have the flexibility to bundle your favourite hotels, airlines and car rental. For the ultimate getaway, why not add some experiences and tours to your travel itinerary?
How do I get a cheap travel package to Madison County?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we've got everything you need. Pick and choose a combination that suits your style and watch your savings pile up. We know a travel package is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotels globally, which lets you customize your Madison County holiday.
What are the top hotels in Madison County?
Have a look at Cobblestone Inn & Suites - Winterset, IA and Covered Bridge Inn. They're the first choice for lots of travellers to Winterset. If Cumming is on your itinerary, Perfect For Families, Friends, And Getaways and Entire Farmhouse In The Country are great options.
How far in advance should I book my Madison County holiday?
You'll be rewarded with the biggest variety at the lowest prices by booking your trip to Madison County early. Air carriers generally advertise flight tickets around 12 months in advance, so start locking things in ASAP. That being said, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Madison County travel package include?
That depends on what kind of getaway you want to have. Madison County holiday deals can include flights, car rentals and hotels. You can mix and match to find the package that suits your needs. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Madison County travel package?
Bundling your bookings into a Madison County holiday package is the most convenient way to organise your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Madison County Expedia holiday package?
Yes, of course. Expedia has access to more than 550 partner airlines all over the world, so fly with the carrier that fits your travel preferences.
If I'm not able to travel, can I cancel my Madison County holiday package?
We understand — unexpected stuff happens. If you've booked a Madison County holiday package and need to cancel or change it, we can help. We recommend having a look at our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a fee.
Stay near popular Madison County attractions
Roseman Bridge
9.6/10 (75 reviews)
You can learn about the history of Winterset when you stop by Roseman Bridge. Make some time to visit the monuments while you're in the area.
Cedar Bridge
9.8/10 (67 reviews)
You can learn about the history of Winterset with a trip to Cedar Bridge. Make some time to visit the monuments while you're in the area.
Photo by Mykayla Powell
Clark Tower
9.6/10 (45 reviews)
You can find out about the history of Winterset with a trip to Clark Tower. Make some time to visit the shops while you're in the area.
Holliwell Bridge
9.6/10 (63 reviews)
Learn about the local history of Winterset when you take a trip to Holliwell Bridge. Make some time to visit the monuments while you're in the area.
John Wayne Birthplace Museum
9.4/10 (131 reviews)
You can spend an afternoon studying the exhibits at John Wayne Birthplace Museum in Winterset. While you're in the area, wander around the natural setting.
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)
You can get tickets for a performance at The Winterset Stage during your trip to Winterset. Make some time to visit the shops while you're in the area.
Cutler-Donahoe Covered Bridge
After visiting Cutler-Donahoe Covered Bridge, make a plan to see the other sights and activities in Winterset. Make some time to visit the shops while you're in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
