Winterset Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winterset

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 3.624.552 ₫ per night from 4 Aug to 5 Aug
3.624.552 ₫
4.059.424 ₫ total
4 Aug - 5 Aug
includes taxes & fees
9.2/10 Wonderful! (780 reviews)
"Nice place. Very comfortable but very over priced."

Reviewed on 26 Jul 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 2.673.729 ₫ per night from 27 Jul to 28 Jul
2.673.729 ₫
2.994.619 ₫ total
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (802 reviews)
"The property is in the middle of renovations. Amenities were very sparse, TV troubles, and very basic breakfast. Not a pleasant stay."

Reviewed on 25 Jul 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 2.869.316 ₫ per night from 23 Aug to 24 Aug
2.869.316 ₫
3.213.634 ₫ total
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"I will stay here again"

Reviewed on 24 Jul 2026

Fairfield Inn and Suites by Marriott Des Moines West
See all 567 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.
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Frequently asked questions

How much does a Winterset holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Winterset costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winterset?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Winterset holiday packages and you could land some great off-season discounts.
How many days is enough for Winterset?
The ideal length for your Winterset holiday depends on what you'd like to do and see. Usually, a few days to a week will give you time to visit all the main sights and discover some hidden spots along the way.
Is it worth booking a holiday package to Winterset?
Winterset is a good holiday destination with attractions like The Winterset Stage among the many things to keep you entertained. Whether you're travelling with the family or getting away with friends, a Winterset holiday promises a good time for everyone.
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 holiday package well in advance.
Is it cheaper to book a Winterset holiday as a package?
An Expedia holiday 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 holiday 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.
How to plan a trip to Winterset?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Winterset.
  2. Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and flights. Your accommodation will likely be the largest expense during your trip to Winterset.
  3. Decide how long to go away for: Now that you're more familiar with Winterset, you can work out the right length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Winterset holiday package that brings all your bookings together.