Hotels in Winterset

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Check prices for these dates

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Winterset?

Porch
Covered Bridge Inn
Covered Bridge Inn
2.5 star property
9.0 out of 10, Wonderful, (769)
The price is $87
$97 total
includes taxes & fees
Dec 23 - Dec 24
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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Budget hotels in Winterset and vicinity

Free WiFi, bed sheets
Motel 6 West Des Moines, IA

Motel 6 West Des Moines, IA

Motel 6 West Des Moines, IA
2.0 star property
West Des Moines
7.8 out of 10, Good, (717)
The price is $51
$57 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Motel 6 West Des Moines, IA
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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When is the best time to visit Winterset?

Our prices for hotels in Winterset are cheapest in January
Price trends for hotels in Winterset
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Winterset
December
Moderate crowds
High 2°C / low -5°C. Partly sunny.
View properties in December
2°
weather_partly_sunny
December, Moderate crowds, average high temperature 2 degrees Celsius, average low temperature -5 degrees Celsius. Partly sunny.
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-1°
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January, Low crowds, average high temperature -1 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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February, Low crowds, average high temperature 0 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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9°
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March, Low crowds, average high temperature 9 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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15°
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April, Moderate crowds, average high temperature 15 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
5°
21°
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May, High crowds, average high temperature 21 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
27°
weather_sun
June, High crowds, average high temperature 27 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
29°
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July, High crowds, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
29°
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August, High crowds, average high temperature 29 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
25°
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September, Moderate crowds, average high temperature 25 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
17°
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October, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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9°
weather_partly_sunny
November, Low crowds, average high temperature 9 degrees Celsius, average low temperature 1 degrees Celsius. Partly sunny.
1°
Monthly weather averages (˚C)

Top landmarks in Winterset

An Old Red Covered Bridge Over A River

Roseman Bridge

4.7/5 (35 reviews)
If you're planning a bit of sightseeing during your trip, head to Roseman Bridge— just one of the landmarks located 7.5 mi (12.1 km) from central Winterset.
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Cedar Bridge under trees - Winterset, Iowa

Cedar Bridge

4.8/5 (30 reviews)
If you're planning a bit of sightseeing during your trip, head to Cedar Bridge— just one of the landmarks located 2.7 mi (4.3 km) from central Winterset.
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Learn more about Winterset

Wander through John Wayne's birthplace, where his childhood home displays memorabilia that would make The Duke tip his hat in approval. The famous covered bridges of Madison County beckon from nearby countryside roads, inspiring bestselling literature and Hollywood romance. Around the town square, antique shops and coffee spots host farmers exchanging conversation over morning cups. Cedar Bridge and Roseman Bridge offer perfect photography backdrops, while Clark Tower provides panoramic views worth the climb. The courthouse stands proudly at the center, a testament to small-town America that Norman Rockwell would recognize. Pammel State Park offers natural respite when Winterset's charm becomes almost too wholesome to bear.

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hogback covered bridge, summer

Check out reviews of Winterset hotels guests love

Wildwood Lodge

Wildwood Lodge

10/10 Excellent
"Room was clean and the bed comfortable - very reasonable rates."
john 2-night trip
Posted 17 hours ago
Wildwood Lodge

Frequently asked questions

What accommodations do travelers like in Winterset?
Cobblestone Inn & Suites - Winterset, IA and Covered Bridge Inn are a couple of accommodations that are popular with guests.
Can I book refundable accommodations in Winterset?
If you're looking for the flexibility to change your travel plans to Winterset, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winterset if I want a vacation rental instead of a hotel?
You'll find 5 vacation homes on our site.
What will the weather in Winterset be like during my vacation?
July and August are typically the warmest months in Winterset when the average temp is 72°F. January and February are the coldest months when the average temperature is 29°F. May and June are the months with the most rain.
Why should I book my Winterset hotel with Hotels.com?
There are lots of reasons to book your Winterset trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.