Book the Best HISTORIC Hotels in Winterset in 2026

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

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1. Cobblestone Inn & Suites - Winterset, IA

Winterset

les

CA $188

CA $211 total

includes taxes & fees

Aug 24 - Aug 25

Combined shower/tub, free toiletries, hair dryer, towels

Deluxe Room, 1 King Bed, Walk Up | Living area

2. Covered Bridge Inn

Winterset

Teresa

CA $140

CA $157 total

includes taxes & fees

Aug 24 - Aug 25

3. Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Winterset

Nickay M.

CA $183

CA $506 total

includes taxes & fees

Aug 25 - Aug 26

4. Lakeside Hotel Casino, a Travelodge by Wyndham

Osceola

Sandra

CA $99

CA $131 total

includes taxes & fees

Aug 24 - Aug 25

5. Edgetowner Motel

De Soto

Brent

CA $80

CA $89 total

includes taxes & fees

Aug 22 - Aug 23

Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower)

6. Sleep Inn Waukee-West Des Moines

Waukee

Sophia

CA $120

CA $134 total

includes taxes & fees

Aug 30 - Aug 31

7. Aloft by Marriott Waukee

Waukee

Gina

CA $133

CA $148 total

includes taxes & fees

Sep 13 - Sep 14

8. Holiday Inn Express & Suites West Des Moines - Jordan Creek by IHG

West Des Moines

Timothy

CA $153

CA $171 total

includes taxes & fees

Sep 17 - Sep 18

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Top Winterset Hotel Reviews

Clarion Inn Des Moines Airport

10/10 Excellent

"Amazing workers. My room was clean. The hotel was clean. The pool was absolutely immaculate. I loved the the heated pool and the water was nice and clear. Parking was amazing. Will definitely be coming back again"

Sheraton West Des Moines Hotel

8/10 Good

"Staff was nice and took care of us promptly"

Drury Inn & Suites West Des Moines

10/10 Excellent

"Great breakfast! Wonderful friendly staff! Love staying at the Drury!!"

Cobblestone Inn & Suites - Winterset, IA

8/10 Good

"It was fine"

Days Inn & Suites by Wyndham Des Moines Airport

8/10 Good

"We came late and left early but the room smelled nice and was tidy. Beds were comfy."

AmericInn by Wyndham Des Moines Airport

10/10 Excellent

"."

Sonesta Simply Suites Des Moines

10/10 Excellent

"One of the best places I have stayed at. Very clean, had a full size refrigerator, had a cooking stove, dishwasher and dishes! Would definitely recommend"

Country Inn & Suites by Radisson, Des Moines West, IA

8/10 Good

"Everything very nice including staff. Breakfast normal hotel breakfast stuff. Pool and hot tub very clean. Right next to Cracker Barrel!"

Motel 6 West Des Moines, IA

8/10 Good

"The only concern I have is that the room did not have a hair dryer, toiletries for your needs. the only soap that was available were 2 very small hand soaps. when I called to request a hair dryer I was informed that they needed my ID and to come to the desk. upon arrival I was informed that I could only use the dryer for 30 minutes because the Hotel only had one! that's impossible to dry your hair whether you just got of the shower and then go to the desk wet."

Frequently asked questions

What can a history enthusiast expect from a trip to Winterset?

Significant historical sites in Winterset are likely a big part of your travel plans. You can also enjoy the many sights to visit such as shopping and restaurants

How many historical hotels are there in Winterset?

In Winterset, you'll find 14 hotels and other lodging options bookable on Expedia though not many historic hotels to choose from.

What are the most important historical places and other sights to visit in Winterset?

Winterset is notable for landmarks like Roseman Bridge, Clark Tower, and Holliwell Bridge. Cultural venues include John Wayne Birthplace Museum and The Winterset Stage. A couple of additional sights to add to your agenda are Cedar Bridge and Rotary Hedge Maze.

What is a historic hotel like in Winterset?

Guests who book a historic hotel can enjoy a vacation someplace that has an officially recognized national historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel as long as it has special significance. Traditional architecture and period features are typically preserved in the guestrooms or communal spaces of these historic hotels in Winterset, giving a historical feel.

What is the difference between a historic hotel and a heritage hotel?

You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is a term often used in the U.S. overall though the terms are similar. The building and architecture of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value along with how it shaped the community.

Do historic hotels in Winterset have modern facilities?

Hotel interiors feature the modern conveniences and safety features you expect to find, though efforts have been made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in most hotels will be available in a historic hotel. Rest assured that when you select a historic hotel in Winterset, you won't find yourself staying at a place that's uncomfortable for guests or simply rundown.

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