Winterset Vacations from $544

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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.
Wildwood Lodge

Wildwood Lodge

3 out of 5
Price was $624, price is now $544 per person
$544
per person
Sep 10 - Sep 13
found 14 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Des Moines (DSM)
9.6/10 Exceptional! (1,270 reviews)
This is by far our favorite place to stay when we are in Des Moines! They have never let us down in all the years we have been there, and that says a lot!

Reviewed on Jun 24, 2026

Hyatt Place West Des Moines Jordan Creek

Hyatt Place West Des Moines Jordan Creek

3 out of 5
Price was $874, price is now $690 per person
$690
per person
Aug 6 - Aug 11
found 13 hours ago
Roundtrip flight included
Denver (DEN) to Des Moines (DSM)
9.2/10 Wonderful! (1,000 reviews)
The breakfast area was not very clean, food on floor and counter tops,

Reviewed on Jun 21, 2026

Hilton Des Moines Downtown

Hilton Des Moines Downtown

3.5 out of 5
Downtown Des Moines
Price was $1,036, price is now $866 per person
$866
per person
Aug 6 - Aug 11
found 13 hours ago
Roundtrip flight included
Denver (DEN) to Des Moines (DSM)
9/10 Wonderful! (999 reviews)
No hot tub, pool was a bit cooler than we liked. We had a cupboard door that was needing hinge repair, which I requested twice but no repair was done. Everything else was great! Room was nice, beds comfy, pillows were awesome! I was able to get shuttle service to the airport very early. I requested extra coffee, creamer and plastic forks which were promptly delivered by the staff. Elevators require a room key to go anywhere except main lobby, so the room areas were fairly secure. All in all, it's one of the nicer hotels I've stayed in.

Reviewed on Jun 23, 2026

Holiday Inn Express & Suites Des Moines Downtown by IHG

Holiday Inn Express & Suites Des Moines Downtown by IHG

2.5 out of 5
Downtown Des Moines
Price was $749, price is now $640 per person
$640
per person
Sep 10 - Sep 13
found 14 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Des Moines (DSM)
9.2/10 Wonderful! (1,000 reviews)
Nice flexible, staff, clean location!

Reviewed on Jun 14, 2026

Kasa Downtown Des Moines

Kasa Downtown Des Moines

4 out of 5
Downtown Des Moines
Price was $1,029, price is now $898 per person
$898
per person
Aug 6 - Aug 11
found 13 hours ago
Roundtrip flight included
Denver (DEN) to Des Moines (DSM)
9/10 Wonderful! (119 reviews)
very nice and modern place. my only issues are the garbage disposal didnt work, and the pillows are to thick.

Reviewed on May 26, 2026

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Stay near popular Winterset attractions

A red bridge over a calm river with greenery around.

Roseman Bridge

9.6/5 (75 reviews)
This 1883 wooden bridge gained fame in "The Bridges of Madison County" film with its distinctive flat roof and lattice design. Visit during autumn when vibrant foliage creates a perfect backdrop for photography.
See properties

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
$128 nightly
The price is $143 total per night from Jul 6 to Jul 7
$143 total
Jul 6 - Jul 7
Total with taxes and fees
9.2/10 Wonderful! (757 reviews)
"Nice place the staff was very nice and a nice breakfast"

Reviewed on Jun 24, 2026

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
$113 nightly
The price is $126 total per night from Jun 28 to Jun 29
$126 total
Jun 28 - Jun 29
Total with taxes and fees
9/10 Wonderful! (796 reviews)
"Hotel is currently undergoing a remodel, but still in great shape......the staff was beyond helpful and friendly.......the site and room were very clean and comfortable.......will definitely stay there again"

Reviewed on Jun 23, 2026

Covered Bridge Inn
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
$74 nightly
The price is $83 total per night from Jun 29 to Jun 30
$83 total
Jun 29 - Jun 30
Total with taxes and fees
8.6/10 Excellent! (1,814 reviews)
"The Days Inn by Wyndham is a nice place to stay. The hotel staff is very helpful, the breakfast has fresh coffee, scrambled eggs, and other selections. The indoor pool is clean and about 20' x 30', a lot of fun. The beds are comfortable and all the linens are clean and fresh. Thank you for a wonderful ..."

Reviewed on Jun 26, 2026

Days Inn & Suites by Wyndham Des Moines Airport
See all 563 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

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Frequently asked questions

How much does a Winterset vacation package cost?
Offering great value package deals from $544 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.

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