Winterset Vacations

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  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Winterset Vacation Packages

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 AEDĀ 421 per night from Nov 19 to Nov 20
AEDĀ 421
AEDĀ 471 total
19 Nov - 20 Nov
includes taxes & fees
9.2/10 Wonderful! (840 reviews)
"Stayed for two nights. Room was clean. Food was so so."

Reviewed on 10 November 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 AEDĀ 339 per night from Nov 12 to Nov 13
AEDĀ 339
AEDĀ 380 total
12 Nov - 13 Nov
includes taxes & fees
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
The price is AEDĀ 458 per night from Nov 15 to Nov 16
AEDĀ 458
AEDĀ 513 total
15 Nov - 16 Nov
includes taxes & fees
9.6/10 Exceptional! (1,424 reviews)
"Room was super clean, spacious and staff was amazing and very helpful. The bar is super cool. Hint: speakeasy"

Reviewed on 11 November 2026

Hotel Fort Des Moines, Curio Collection by Hilton
See all 529 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.

Stay near popular Winterset attractions

A red bridge over a calm river with greenery around.

Roseman Bridge

9.6/10 (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

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 ā€” perfect for a budget-friendly getaway.
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 favorite 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.