Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀

Hotels in Winterset

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
May 11 - May 12
Tomorrow
May 12 - May 13
Next weekend
May 16 - May 18
In two weeks
May 23 - May 25

Where to stay in Winterset?

Cobblestone Inn & Suites - Winterset, IA
Lobby

Cobblestone Inn & Suites - Winterset, IA

2.5 star property
9.2 out of 10, Wonderful, (626)
$119 nightly
The price is $134
May 12 - May 13
Total includes taxes and fees
Cobblestone Inn & Suites - Winterset, 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.
trending_down

Our prices for hotels in Winterset are cheapest in February

See average prices and weather for all months

Price trends for hotels in Winterset

Pricing is based on two traveler single night rates
May
$138
Average price during May is $138
Jun
$143
Average price during June is $143
Jul
$136
Average price during July is $136
Aug
$154
Average price during August is $154
Sep
$142
Average price during September is $142
Oct
$148
Average price during October is $148
Nov
$102
Average price during November is $102
Dec
$93
Average price during December is $93
Jan
$89
Average price during January is $89
Feb
$79
Average price during February is $79
Mar
$107
Average price during March is $107
Apr
$93
Average price during April is $93
Currently viewing crowd sizes and weather for May.

May

trending_upHigh crowds
High 70°F / low 52°F. Sunny most days.
70°
weather_sun
May, High crowds, average high temperature 70 degrees Fahrenheit, average low temperature 52 degrees Fahrenheit. Sunny most days.
52°
80°
weather_sun
June, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 63 degrees Fahrenheit. Sunny most days.
63°
84°
weather_sun
July, High crowds, average high temperature 84 degrees Fahrenheit, average low temperature 66 degrees Fahrenheit. Sunny most days.
66°
83°
weather_sun
August, High crowds, average high temperature 83 degrees Fahrenheit, average low temperature 64 degrees Fahrenheit. Sunny most days.
64°
78°
weather_sun
September, Moderate crowds, average high temperature 78 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
57°
63°
weather_sun
October, Moderate crowds, average high temperature 63 degrees Fahrenheit, average low temperature 45 degrees Fahrenheit. Sunny most days.
45°
49°
weather_partly_sunny
November, Low crowds, average high temperature 49 degrees Fahrenheit, average low temperature 33 degrees Fahrenheit. Partly sunny.
33°
36°
weather_partly_sunny
December, Moderate crowds, average high temperature 36 degrees Fahrenheit, average low temperature 23 degrees Fahrenheit. Partly sunny.
23°
29°
ac_unit
January, Low crowds, average high temperature 29 degrees Fahrenheit, average low temperature 15 degrees Fahrenheit. Snow likely.
15°
33°
ac_unit
February, Low crowds, average high temperature 33 degrees Fahrenheit, average low temperature 17 degrees Fahrenheit. Snow likely.
17°
48°
weather_cloudy
March, Low crowds, average high temperature 48 degrees Fahrenheit, average low temperature 32 degrees Fahrenheit. Cloudy most days.
32°
60°
weather_partly_sunny
April, Moderate crowds, average high temperature 60 degrees Fahrenheit, average low temperature 41 degrees Fahrenheit. Partly sunny.
41°
Monthly weather averages (˚F)
View all properties

Top landmarks in Winterset

#adventure Built in 1883 by Harvey P. Jones and George K. Foster, Roseman is 107 feet in length and sits in its original location. It was renovated in 1992 at a cost of $152,515. In Robert James Waller’s novel, The Bridges of Madison County, and the movie of the same name, Roseman is the bridge Robert Kincaid seeks when he stops at Francesca Johnson’s home for directions. It is also where Francesca leaves her note inviting him to dinner. Also known as the “haunted” bridge, Roseman is where two sheriff’s posses trapped a county jail escapee in 1892. It is said the man rose up straight through the roof of the bridge, uttering a wild cry, and disappeared. He was never found, and it was decided that anyone capable of such a feat must be innocent.

Roseman Bridge

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.

See properties in Roseman Bridge
Roseman Bridge

Learn more about Winterset

Winterset is applauded for its cultural attractions such as John Wayne Birthplace Museum and The Winterset Stage. This welcoming city has something for everyone including sights like Madison County Courthouse and Clark Tower within a small-town setting.

See all hotels in Winterset
#adventure Built in 1883 by Harvey P. Jones and George K. Foster, Roseman is 107 feet in length and sits in its original location. It was renovated in 1992 at a cost of $152,515. In Robert James Waller’s novel, The Bridges of Madison County, and the movie of the same name, Roseman is the bridge Robert Kincaid seeks when he stops at Francesca Johnson’s home for directions. It is also where Francesca leaves her note inviting him to dinner. Also known as the “haunted” bridge, Roseman is where two sheriff’s posses trapped a county jail escapee in 1892. It is said the man rose up straight through the roof of the bridge, uttering a wild cry, and disappeared. He was never found, and it was decided that anyone capable of such a feat must be innocent.
Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀
Open Photo by Tonette Pineda✈⛵🚌🚉🚃🚅🚀
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
Sign in or join for free

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 with my pet in Winterset?
Your furry friend can stay with you at these pet-friendly hotels: Covered Bridge Inn, Cobblestone Inn & Suites - Winterset, IA and Charming 1855 Stone Farmhouse Retreat – Cozy Stays & Picturesque Views Await.
Which Winterset hotels do travelers like for their great location?
Our guests rave about the location of Cobblestone Inn & Suites - Winterset, IA.
Where can I stay in Winterset if I'm looking for an affordable accommodation?
An inexpensive option worth considering is Cobblestone Inn & Suites - Winterset, IA.
Where can I stay if I'm traveling to Winterset for a family-friendly trip?
Your kids are welcome at Covered Bridge Inn, Cobblestone Inn & Suites - Winterset, IA and Entire farmhouse in the country.
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.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

https://www.hotels.com/lp/b/deals