Winterset Vacations from $711

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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.
Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

3 out of 5
Price was $842, price is now $711 per person
$711
per person
Jul 17 - Jul 21
found 7 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Des Moines (DSM)
9.2/10 Wonderful! (1,002 reviews)
Clean but bed is too high and like a rock.

Reviewed on May 30, 2026

Hampton Inn West Des Moines Lake Drive

Hampton Inn West Des Moines Lake Drive

3 out of 5
Price was $869, price is now $718 per person
$718
per person
Jul 17 - Jul 21
found 7 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Des Moines (DSM)
8.8/10 Excellent! (1,002 reviews)
Clean rooms but smaller than what I'm used to for a hampton. The staff could be more welcoming but then again I didn't have much interaction with them. The pool had no towels and the basket that had the dirty towels were overflowing. Would've been nice to have towels stocked for a weekend.

Reviewed on May 12, 2026

SpringHill Suites Des Moines West

SpringHill Suites Des Moines West

3 out of 5
Price was $902, price is now $755 per person
$755
per person
Jul 17 - Jul 21
found 7 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Des Moines (DSM)
8.6/10 Excellent! (1,002 reviews)
Clean, comfortable room and an enjoyable breakfast.

Reviewed on May 20, 2026

Homewood Suites By Hilton Urbandale Des Moines

Homewood Suites By Hilton Urbandale Des Moines

3 out of 5
Price was $934, price is now $788 per person
$788
per person
Jul 17 - Jul 21
found 7 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Des Moines (DSM)
10/10 Exceptional! (7 reviews)
This is the cleanest place we have ever stayed in. The breakfast is great with a lot of options. The staff are extremely helpful and very friendly. This last time was our only 2nd time there and both times, have been the best.

Reviewed on May 27, 2026

My Place Hotel - Altoona/Des Moines, IA

My Place Hotel - Altoona/Des Moines, IA

3 out of 5
Price was $1,073, price is now $914 per person
$914
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Des Moines (DSM)
8.8/10 Excellent! (993 reviews)
Nice place for the price.

Reviewed on May 22, 2026

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Discover the most popular places to visit in Winterset

An Old Red Covered Bridge Over A River

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
Clark Tower

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
An Old Red Covered Bridge

Holliwell Bridge

4.5/5(6 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.

Holliwell Bridge

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
$124 nightly
The price is $139 total per night from Jun 1 to Jun 2
$139 total
Jun 1 - Jun 2
Total with taxes and fees
9.2/10 Wonderful! (744 reviews)
"Great value in this mid west town. Reasonably priced, clean & convenient."

Reviewed on May 22, 2026

Cobblestone Inn & Suites - Winterset, IA
Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd. Winterset IA
$113 nightly
The price is $126 total per night from Jun 3 to Jun 4
$126 total
Jun 3 - Jun 4
Total with taxes and fees
9/10 Wonderful! (791 reviews)
"In the middle of renovations but was hardly noticeable. Everyone was super kind and friendly. Very quiet. Decent breakfast in an out of the way room."

Reviewed on May 27, 2026

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
$144 nightly
The price is $161 total per night from Jun 7 to Jun 8
$161 total
Jun 7 - Jun 8
Total with taxes and fees
9.6/10 Exceptional! (1,159 reviews)
"Luxury! Would stay anytime."

Reviewed on May 26, 2026

Hotel Fort Des Moines, Curio Collection by Hilton
See all 562 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 $711 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.