Madison County Vacation Packages
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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.
Top Madison County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Quality Inn Fairfield
CA $1,304
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Des Moines (DSM)
8.2/10 Very good! (446 reviews)
While the staff was very polite they were working against a clearly aging "landlord special" property. This at best is a 80.00 per night hotel. To charge 130.00+ a night for a stay here is absolutely a slap in the face. The toilets flushed nerve rackingly slow, the shower curtain rod was almost falling off the wall. Showers water pressure was very low and took 30 minutes to rinse shampoo out of hair. The ceiling in the bathroom was cracking and peeling off, there was a blood stain on our blanket that was NOT from us. The handle on the sink fell off while turning water on. The pool- while clean, was too cold to enjoy... But the room was clean! We had to leave 2 nights early due to a family emergency and they could not check us out early due to a night audit, but "left a note" to check us out in the AM. Not sure they did until I called today to verify. Again staff was nice and tried to be helpful, hotel was as clean as they could possibly make it,,but the WHOLE place needs an overhaul for this price. If we weren't just staying for a place to crash while cleaning out my father's estate and this was a vacation stay I would have been very disappointed. Everything we were disappointed about in this stay was nothing staff could help with or change, so we did not bring any of it to anyones attention just dealt with ourselves and moved on as we were just already exhausted from a 14hr drive and 2 days of cleaning out my late father's house. Quality inn is off our stay list.
Reviewed on Oct 12, 2026
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 $177
CA $198 total
Nov 15 - Nov 16
includes taxes & fees
9.6/10 Exceptional! (1,379 reviews)
"The elevator in the parking ramp was broken, so I had to wrestle my luggage down three flights of stairs. Easy solution: valet parking. This hotel is on the historic registry, so if something's broken it must go through careful reviews before any repairs can begin. Just something to be aware of."
Reviewed on Oct 16, 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 $139
CA $156 total
Nov 16 - Nov 17
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Greeted by freindly staff which always accommodating. Very convenient location to major highways and accessible to the places our family wanted to see. Great rooms, great breakfasts, and the two year old loved the pool. Priced right for the area."
Reviewed on Oct 13, 2026
Stoney Creek Hotel Des Moines - Johnston
5291 Stoney Creek Court Johnston IA
Fully refundableReserve now, pay when you stay
CA $123
CA $138 total
Oct 20 - Oct 21
includes taxes & 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.
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 CA $1,304. 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.
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.
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.
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.
