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.
Wildwood Lodge

Wildwood Lodge

3 out of 5
Price was CA $988, price is now CA $919 per person
CA $919
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Des Moines (DSM)
9.6/10 Exceptional! (1,237 reviews)
Very comfortable mattress

Reviewed on Jul 1, 2026

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 CA $1,199, price is now CA $1,093 per person
CA $1,093
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Des Moines (DSM)
9.6/10 Exceptional! (1,202 reviews)
The hotel is really top notch and in an historic building. Beautifully maintained. Parking is a bit expensive. Nice casual restaurant in the lobby floor has a good selection for breakfast, lunch, etc.

Reviewed on Jun 30, 2026

Hyatt Place West Des Moines Jordan Creek

Hyatt Place West Des Moines Jordan Creek

3 out of 5
Price was CA $1,299, price is now CA $1,190 per person
CA $1,190
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Des Moines (DSM)
9.2/10 Wonderful! (1,004 reviews)
Thank you! See you again soon!

Reviewed on Jun 30, 2026

Hotel Renovo Des Moines Urbandale,Tapestry Collection Hilton

Hotel Renovo Des Moines Urbandale,Tapestry Collection Hilton

3.5 out of 5
Price was CA $1,003, price is now CA $925 per person
CA $925
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Des Moines (DSM)
9.2/10 Wonderful! (1,001 reviews)
We enjoyed our stay. Was quiet, thick walls we think because a little league team was running around the halls while we were there but we only noticed when we weren't inside our room. Staff was friendly and very casual. Beautiful lobby.

Reviewed on Jun 29, 2026

Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

3 out of 5
Price was CA $1,043, price is now CA $967 per person
CA $967
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Des Moines (DSM)
9.2/10 Wonderful! (1,005 reviews)
Weird stains on the sleeper sofa as well as the light fixtures. No additional bedsheets found in linen closet. Rancid smell in room, very few outlets. Roach found in bathroom, very stained and mildewed shower curtain. Refrigerator hardly cold enough to store food. Really dingy and unclean vibe overall, and very outdated property. Breakfast pretty standard. + 1 star for working AC.

Reviewed on Jul 2, 2026

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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
The price is CA $182 per night from Jul 7 to Jul 8
CA $182
CA $204 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (760 reviews)
"Great place"

Reviewed on Jul 1, 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
The price is CA $144 per night from Jul 19 to Jul 20
CA $144
CA $161 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (799 reviews)
"The motel is in the process of remodeling. What I saw was very nice. My room was clean and neat. I have worked in the motel business a long time ago and I am critical of a lot of things. This motel filled my needs and will be very nice when complete. I met three members of the staff and they were ..."

Reviewed on Jun 30, 2026

Covered Bridge Inn
Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

3 out of 5
7225 Vista Dr West Des Moines IA
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 5 to Jul 6
CA $155
CA $174 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Weird stains on the sleeper sofa as well as the light fixtures. No additional bedsheets found in linen closet. Rancid smell in room, very few outlets. Roach found in bathroom, very stained and mildewed shower curtain. Refrigerator hardly cold enough to store food. Really dingy and unclean vibe overall, ..."

Reviewed on Jul 2, 2026

Fairfield Inn and Suites by Marriott Des Moines West
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.
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Stay near popular Winterset attractions

A red bridge over a calm river with greenery around.

Roseman Bridge

9.6/10 (75 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.
See properties

Frequently asked questions

How much does a Winterset vacation package cost?
You can grab a vacation package to this popular destination from CA $919 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.

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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.