Winterset Vacations from $482

Book a Hotel + Flight or Car together to unlock savings

Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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 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.
Hampton Inn & Suites Ankeny

Hampton Inn & Suites Ankeny

2.5 out of 5
Price was $557, price is now $482 per person
$482
per person
Jan 16 - Jan 19
found 7 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Des Moines (DSM)
8.8/10 Excellent! (470 reviews)
Great hotel, place was taken very well care of.

Reviewed on Nov 24, 2025

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 $684, price is now $573 per person
$573
per person
Feb 19 - Feb 21
found 10 hours ago
Roundtrip flight included
New York (LGA) to Des Moines (DSM)
9.6/10 Exceptional! (1,037 reviews)
This is our second time staying here. It feels like a 5 star hotel. The details in the decor are unique and well designed. The bed and bedding is comfortable. I love the lobby, large and spacious with lots of seating options for gatherings small or large. Great restaurant, Proudfoot and Bird with a bar that has great happy hour from 2-6 daily. The happy hour has great food options, not so much for drinks on special. The HOBNob restaurant for breakfast is ok, but service there is slow. Will definitely stay there again. Great price for the quality of the hotel.

Reviewed on Dec 6, 2025

Wildwood Lodge

Wildwood Lodge

3 out of 5
Price was $592, price is now $510 per person
$510
per person
Jan 16 - Jan 19
found 7 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Des Moines (DSM)
9.6/10 Exceptional! (1,194 reviews)
Room was nice, staff was very nice. We would stay there again

Reviewed on Nov 23, 2025

Holiday Inn Downtown - Mercy Area by IHG

Holiday Inn Downtown - Mercy Area by IHG

3 out of 5
Downtown Des Moines
Price was $551, price is now $488 per person
$488
per person
Jan 16 - Jan 19
found 7 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Des Moines (DSM)
8/10 Very Good! (1,001 reviews)
Hotel was good option for walking to Casey Center for Paul McCartney concert. Lobby was filled with concert goers end of evening, and it took hotel over 30 minutes to open stairwell. People were piled up in lobby, security was nowhere to be found, and front desk didn't have keys to open stairwell. People were tired, had to use bathroom, etc, and it took too long to accommodate the guests needs.

Reviewed on Nov 16, 2025

Hyatt Place West Des Moines Jordan Creek

Hyatt Place West Des Moines Jordan Creek

3 out of 5
Price was $586, price is now $522 per person
$522
per person
Jan 16 - Jan 19
found 7 hours ago
Roundtrip non-stop flight included
Birmingham (BHM) to Des Moines (DSM)
9.2/10 Wonderful! (1,004 reviews)
Everything was very good,

Reviewed on Dec 1, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winterset
View all trips

Discover the most popular places to visit in Winterset

#adventure Built in 1883 by Harvey P. Jones and George K. Foster, Roseman is 107 feet in length and sits in its original location. It was renovated in 1992 at a cost of $152,515. In Robert James Waller’s novel, The Bridges of Madison County, and the movie of the same name, Roseman is the bridge Robert Kincaid seeks when he stops at Francesca Johnson’s home for directions. It is also where Francesca leaves her note inviting him to dinner. Also known as the “haunted” bridge, Roseman is where two sheriff’s posses trapped a county jail escapee in 1892. It is said the man rose up straight through the roof of the bridge, uttering a wild cry, and disappeared. He was never found, and it was decided that anyone capable of such a feat must be innocent.

Roseman Bridge

4/5(5 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.

Roseman Bridge
On a stop over going to Whistler Mountain #blue #wanderwoman #Canada #takemeback

Clark Tower

4/5(4 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.

Clark Tower

John Wayne Birthplace Museum

4.5/5(62 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.

John Wayne Birthplace Museum

Winterset Hotel Deals

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
1304 North 4th Avenue Winterset IA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $119 total per night from Dec 10 to Dec 11
$119 total
Dec 10 - Dec 11
Total with taxes and fees
9.2/10 Wonderful! (710 reviews)
Nice place

Reviewed on Nov 26, 2025

Cobblestone Inn & Suites - Winterset, IA
Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd. Winterset IA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $97 total per night from Dec 10 to Dec 11
$97 total
Dec 10 - Dec 11
Total with taxes and fees
9/10 Wonderful! (766 reviews)
Yes

Reviewed on Nov 27, 2025

Covered Bridge Inn
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
$143 nightly
The price is $160 total per night from Jan 4 to Jan 5
$160 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,068 reviews)
The staff was very friendly and helpful. The hotel itself is beautiful and was great for our stay in Des Moines.

Reviewed on Dec 3, 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 576 properties in Winterset
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

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winterset vacation package cost?
Offering great value package deals from $482 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.