Winterset Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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!

Ready to book your vacation to Winterset?

 

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Winterset Hotel Deals

Covered Bridge Inn

Covered Bridge Inn

2.5 out of 5
1312 Cedar Bridge Rd., Winterset, IA
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Aug 10 to Aug 11
CA $122
CA $134 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (715 reviews)
"The workers were so kind and helpful! We were there for a music festival so they were booked up, but when we called and requested an earlier checkin time they were flexible and made it happen for us! The staff are very accommodating and you can tell that they want their guests to be comfortable and ..."

Reviewed on Aug. 4, 2025

Covered Bridge Inn
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
The price is CA $185 per night from Aug 17 to Aug 18
CA $185
CA $208 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (658 reviews)
"Excellent value and convenient to spots of interest"

Reviewed on Aug. 1, 2025

Cobblestone Inn & Suites - Winterset, IA
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 $191 per night from Aug 17 to Aug 18
CA $191
CA $214 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"Can’t say enough about the dining options on property. The café coffee is some of the best I’ve ever had. The mac & cheese there is to die for. And the daily happy hour at the upscale restaurant was also amazing. Staff was amazing and I certainly will never stay anywhere else in Iowa."

Reviewed on Aug. 6, 2025

Hotel Fort Des Moines, Curio Collection by Hilton
See all 530 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.
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Frequently asked questions

How much does a Winterset vacation package cost?
You can grab a vacation package to this popular destination on Expedia. However, how much your vacation to Winterset costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Winterset?
If you'd like to score a cheap Winterset vacation package, consider visiting in December, January and February. You'll usually find better prices on hotels and airfares during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Winterset?
Usually, a handful of days is enough to visit the major sights during your Winterset vacation. However, if you prefer to have some time to chill out or go on day trips, consider extending your itinerary.
Is it worth booking a vacation package to Winterset?
It's no wonder a Winterset vacation is on the to-do list of many travellers. Well-known attractions like The Winterset Stage are just the beginning of what you can explore here.
How to find the best Winterset package deals?
Use Expedia's handy filters to help you find some terrific Winterset package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Winterset package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winterset vacation as a package?
You can enjoy significant savings on your next Winterset escape by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winterset?
Score amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Winterset vacation.
How to plan a trip to Winterset?

  1. Choose when to go: Check your schedule and get packing. Your favourite time of year and the available activities will also help you decide when to visit Winterset.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to airfares and activities. Your accommodations will likely be the largest expense during your trip to Winterset.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Winterset. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a Winterset vacation package that brings all your bookings together.

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