Winterset Vacation Packages

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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!

Top Winterset Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Des Moines Airport

Baymont by Wyndham Des Moines Airport

2.5 out of 5
Southwestern Hills
per person
Oct 17 - Oct 20
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Des Moines (DSM)
9.4/10 Exceptional! (1,045 reviews)
Great affordable quiet place to stay. We have stayed here a couple times now, and we'll stay again.

Reviewed on Aug. 6, 2025

Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

2.5 out of 5
per person
Oct 17 - Oct 20
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Des Moines (DSM)
9.2/10 Wonderful! (918 reviews)
Wonderful location, they had to relocate us to sister property and make sure we got a suite do to issues beyond their control

Reviewed on Aug. 2, 2025

Holiday Inn Downtown - Mercy Area by IHG

Holiday Inn Downtown - Mercy Area by IHG

3 out of 5
Downtown Des Moines
per person
Oct 17 - Oct 20
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Des Moines (DSM)
8/10 Very Good! (1,003 reviews)
Hotel sits over the interstate and it was noisy all night. Homeless in the area, but property had armed security guard in the lobby. Can't walk to restaurants in downtown Des Moines.

Reviewed on Aug. 5, 2025

La Quinta by Wyndham Altoona Des Moines

La Quinta by Wyndham Altoona Des Moines

3 out of 5
per person
Oct 17 - Oct 20
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Des Moines (DSM)
9/10 Wonderful! (1,557 reviews)
We had a good experience! Property is in decent shape with some maintenance underway on the 4th floor. Clean rooms and nice staff. For the weekly rate, it was worth the cost, but can’t attest to weekend rates. We would come back again if in the area.

Reviewed on Aug. 3, 2025

Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

2 out of 5
Greater South Side
per person
Oct 17 - Oct 20
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Des Moines (DSM)
8.4/10 Very Good! (1,581 reviews)
They gave us our key to our room and when we went to open the door there were already people in that room and we walked in on them, luckily they were nice about it. They switched our room but then we had someone using their key to try and get into our room a couple days later which thankfully ours was bolted. It’s just unsettling being two young girls with the idea that someone could have just walked in while we were sleeping.

Reviewed on Aug. 5, 2025

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 $123 per night from Aug 10 to Aug 11
CA $123
CA $135 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (713 reviews)
"The bed was comfy and I got a good night's sleep"

Reviewed on Jul. 31, 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 $180 per night from Sep 5 to Sep 6
CA $180
CA $202 total
Sep 5 - Sep 6
includes taxes & fees
9.2/10 Wonderful! (656 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 $190 per night from Aug 24 to Aug 25
CA $190
CA $212 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"Lobby beautiful and photogenic. Old time elevators. Nice restaurant. So fun@"

Reviewed on Aug. 2, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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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 from CA $835 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.