Madison County Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Madison County Vacation
Leave all the planning to us with a Madison County vacation package. With everything organized before you go, the only thing left to do is relax and experience this destination's beauty and culture. You'll have a to-do list as long as your arm during your trip to Madison County. One leading city you'll want to spend some time exploring is Winterset. Expedia has hotels, flights, car rentals and more to help you curate your very own customized Madison County vacation today.
Madison County Hotel Deals
Hotel Fort Des Moines, Curio Collection by Hilton
1000 Walnut St Des Moines IA
Fully refundableReserve now, pay when you stay
CA $180
CA $202 total
Nov 8 - Nov 9
includes taxes & fees
9.6/10 Exceptional! (1,363 reviews)
"Really cool hotel with history. Great location and clean nice room."
Reviewed on Oct 10, 2026
Fairfield Inn and Suites by Marriott Des Moines West
7225 Vista Dr West Des Moines IA
Fully refundableReserve now, pay when you stay
CA $138
CA $154 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"I was impressed with the kitchen in the room but honestly everything was in dire need of updating and basic maintenance. Trim boards broken partway up the door frame for example. It served purpose needs for a one night stay but not the destination for a weekend getaway."
Reviewed on Oct 10, 2026
Stoney Creek Hotel Des Moines - Johnston
5291 Stoney Creek Court Johnston IA
Fully refundableReserve now, pay when you stay
CA $139
CA $156 total
Oct 11 - Oct 12
includes taxes & fees
8.8/10 Excellent! (1,922 reviews)
"NA"
Reviewed on Oct 10, 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 vacation 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 favorite 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 vacation.
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 travelers 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 vacation?
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 vacation!
What does an Expedia Madison County travel package include?
That depends on what kind of getaway you want to have. Madison County vacation 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 vacation package is the most convenient way to organize 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 vacation 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 vacation package?
We understand — unexpected stuff happens. If you've booked a Madison County vacation 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 with a stop at 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 when you stop by 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 stop at 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 spend time at 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 browsing 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 enjoy a show at The Winterset Stage during your stay in 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.
