A red covered bridge over a calm river, surrounded by lush greenery and trees.

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Our top choices for Winterset luxury hotels

A hotel entrance with a stone facade, a sign above the entrance, and a covered walkway.

1. Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA
2.5 star property
Winterset
9.2 out of 10, Wonderful, (837 reviews)
"Pleasant stay"
United States
Lindsey
The price is ₩159,725
₩178,894 total
includes taxes & fees
Nov 10 - Nov 11
Cobblestone Inn & Suites - Winterset, IA
A covered outdoor area with a wooden ceiling and brick pillars, overlooking a parking lot with cars and a distant landscape.

2. Covered Bridge Inn

Covered Bridge Inn
2.5 star property
Winterset
9.0 out of 10, Wonderful, (823 reviews)
"It was nice to stay at"
United States
Cindy
The price is ₩121,866
₩136,488 total
includes taxes & fees
Nov 22 - Nov 23
Covered Bridge Inn
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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Top Winterset Hotel Reviews

Days Inn & Suites by Wyndham Des Moines Airport

Days Inn & Suites by Wyndham Des Moines Airport

8/10 Good
"A"
Sue 4-night trip
Posted 4 hours ago
Days Inn & Suites by Wyndham Des Moines Airport
Stoney Creek Hotel Des Moines - Johnston

Stoney Creek Hotel Des Moines - Johnston

10/10 Excellent
"Loved the room, pool and hot tub. Breakfast was good. Will stay again!"
William 1-night trip
Posted 14 hours ago
Stoney Creek Hotel Des Moines - Johnston

Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in Winterset?
Use Expedia to arrange your flight to Des Moines International Airport (DSM) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a vacation, so we make it easy to get what you'd like to make your stay special. If you want a posh hotel that has fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Winterset offers. Winterset has some interesting things to see and do including John Wayne Birthplace Museum and Clark Tower, so you might want to take in the local sights during your visit.
When can I expect good weather in Winterset?
Planning for the weather is a good way to make your trip to Winterset relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Winterset are January, February, November, and March, with each month seeing an average of 9 inches of snowfall.
What's there to see and do in Winterset?
Experience Winterset and visit John Wayne Birthplace Museum, Clark Tower, and The Winterset Stage. If you have a little extra time during your trip, you might want to check out Cedar Bridge and Roseman Bridge.