Madison County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.

Top Madison County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wildwood Lodge

Wildwood Lodge

3 out of 5
Price was CA $1,653, price is now CA $1,383 per person
CA $1,383
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
9.6/10 Exceptional! (1,253 reviews)
I loved everything about our stay…the staff was friendly and accommodating, the breakfast was wonderful and the ambiance was perfect.

Reviewed on Jun 11, 2026

Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
Downtown Des Moines
Price was CA $2,450, price is now CA $1,969 per person
CA $1,969
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
9.6/10 Exceptional! (1,171 reviews)
This is really the only place to stay in Des Moines. It is so gorgeous. The scale of it is amazing. Everything from the Cool statues and artwork in the library to the rooms themselves are just beautiful. Bravo!

Reviewed on Jun 9, 2026

Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

3 out of 5
Price was CA $1,741, price is now CA $1,467 per person
CA $1,467
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
9.2/10 Wonderful! (1,005 reviews)
Clean and friendly stuff

Reviewed on Jun 12, 2026

SpringHill Suites Des Moines West

SpringHill Suites Des Moines West

3 out of 5
Price was CA $1,703, price is now CA $1,437 per person
CA $1,437
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
8.6/10 Excellent! (1,009 reviews)
The room was clean, the staff went out of their way to help us with more bedding and towels, the breakfast was good, could have a few more choices, but way better than some other places. The hot tub was hot, which is very good.

Reviewed on Jun 11, 2026

Hotel Renovo Des Moines Urbandale,Tapestry Collection Hilton

Hotel Renovo Des Moines Urbandale,Tapestry Collection Hilton

3.5 out of 5
Price was CA $1,655, price is now CA $1,400 per person
CA $1,400
per person
Jul 29 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Des Moines (DSM)
9.2/10 Wonderful! (1,003 reviews)
It was a beautiful property in a convenient location!

Reviewed on Jun 12, 2026

Madison County Hotel Deals

Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
1000 Walnut St Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Jul 3 to Jul 4
CA $205
CA $229 total
Jul 3 - Jul 4
includes taxes & fees
9.6/10 Exceptional! (1,185 reviews)
"It was great"

Reviewed on Jun 11, 2026

Hotel Fort Des Moines, Curio Collection by Hilton
Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

3 out of 5
7225 Vista Dr West Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Jun 21 to Jun 22
CA $152
CA $171 total
Jun 21 - Jun 22
includes taxes & fees
9.2/10 Wonderful! (1,018 reviews)
"roof leaked onto bed and they knew that room was a problem"

Reviewed on Jun 13, 2026

Fairfield Inn and Suites by Marriott Des Moines West
Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

2 out of 5
1901 Hackley Ave Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $101 per night from Jun 15 to Jun 16
CA $101
CA $113 total
Jun 15 - Jun 16
includes taxes & fees
8.6/10 Excellent! (1,822 reviews)
"Parking was easy and spacious, stayed in a non-smoking room and didn’t have a whiff of smoke at all. Can’t comment on breakfast as we chose to sleep in, but from 4am-10am the longest I’ve ever seen from a hotel which was awesome. Rooms were clean and spacious, the bed was comfortable and the bathroom ..."

Reviewed on Jun 12, 2026

Days Inn & Suites by Wyndham Des Moines Airport
See all 867 properties in Madison County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,383. 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

An Old Red Covered Bridge Over A River

Roseman Bridge

4.8/5 (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.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.