Book the Best HISTORIC Hotels in Winterset in 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Winterset Historic Hotels

Tonight

Tomorrow

This weekend

Next weekend

No exact matches found, but these alternatives could be just right

Recommended hotels in Winterset

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

A hotel room with a large bed, a desk with a chair, a lamp, and a window with curtains.

A hotel lobby with a reception desk, a brown sofa, a small armchair, a coffee table, and a fireplace.

A bar area with a stone wall, a TV mounted on the wall, and a refrigerator.

1. Cobblestone Inn & Suites - Winterset, IA

Winterset

Joseph

CA $131

CA $147 total

includes taxes & fees

Nov 4 - Nov 5

A covered outdoor area with a wooden ceiling and brick pillars, overlooking a parking lot with cars and a distant landscape.

A covered bridge inn with a brick entrance and a covered patio area.

A hotel room with a grey patterned carpet, a grey sofa with cushions, a wooden cabinet, a television, a small refrigerator, and a window with pink curtains.

A hotel room with two beds, a desk with a computer, a TV, and a window with curtains.

2. Covered Bridge Inn

Winterset

Cindy

CA $126

CA $141 total

includes taxes & fees

Oct 18 - Oct 19

A deck with a table and chairs, surrounded by a wooden deck and a white railing.

A modern kitchen with white cabinets, a central island with bar stools, and a dining area with wooden chairs and a table.

A dining area with a wooden table, chairs, and a chandelier.

A modern kitchen with a central island, bar stools, and a dining area with a view.

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

Winterset

Nickay M.

CA $172

CA $501 total

includes taxes & fees

Oct 20 - Oct 21

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

A vending machine area with a Coca-Cola and Aquafina water dispenser, and a snack vending machine.

A cozy room with a fireplace, wooden walls, and a television. There are four chairs, a table, and a claw machine.

A spacious indoor area with wooden ceiling and walls, featuring a pool table, chairs, and a television screen.

4. Americas Best Value Inn Stuart

Stuart

ROBIN

CA $143

CA $160 total

includes taxes & fees

Oct 23 - Oct 24

A modern hotel with a large, illuminated entrance canopy and a prominent 'HOTELS' sign.

A modern lounge area with sofas, ottomans, and a bar area.

A bar area with a 'WXYZ' sign, multiple shelves of liquor bottles, and four black bar stools.

A modern lounge area with a sofa, round tables, and chairs, featuring a patterned rug and a view of the dining area.

5. Aloft by Marriott Waukee

Waukee

Gina

CA $131

CA $147 total

includes taxes & fees

Oct 18 - Oct 19

A single-story motel with a small front porch and a sign indicating it is a motel office.

A hotel room with a bed, a sofa, a television, and a view of the outside.

A hotel room with two beds, a bathroom, and a small desk area.

A single-story motel with a beige exterior, a covered parking area, and a small garden with pink flowers.

6. Edgetowner Motel

De Soto

Brent

CA $72

CA $80 total

includes taxes & fees

Nov 4 - Nov 5

A small, single-story building with a flat roof and a large glass door. There are two potted plants on either side of the entrance, and a small trash can to the right.

A covered outdoor area with a white SUV parked under a canopy.

A living room with a television, a potted plant, a window with a view, a brown leather chair, and a small table.

A room with a window, a desk with a coffee maker, a trash can, and two wall decorations.

7. Stuart Motor Lodge

Stuart

Heath

CA $92

CA $104 total

includes taxes & fees

Nov 1 - Nov 2

A modern lobby with a sofa, chairs, a lamp, and a wall with a floral pattern.

A modern restaurant with a variety of seating options including tables, chairs, and sofas.

A MainStay Suites hotel with a modern design, parking lot, and a clear sky.

A hotel room with a bed, a desk, a chair, and a nightstand with lamps.

8. Sleep Inn Waukee-West Des Moines

Waukee

Paul

CA $120

CA $135 total

includes taxes & fees

Nov 1 - Nov 2

View all properties

Top Winterset Hotel Reviews

Wildwood Lodge

10/10 Excellent

"The staff is really friendly, the breakfast is good and the rooms are clean"

Cobblestone Inn & Suites - Winterset, IA

8/10 Good

"I thought I rented a lower room and ended up having to do stairs no elevator I would rather they lower the price and go to Hardee’s for breakfast than to eat what they had there again was very poor quality for a breakfast"

Baymont by Wyndham Des Moines Airport

10/10 Excellent

"Everything was comfortable in my kids enjoyed it. We all had a good time."

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

10/10 Excellent

"Clean room, comfy bed, friendly staff, breakfast was good, pool was bigger than a regular hotel pool, hot tub was as well. Would definitely stay here again. Probably will next time in Des Moines."

Sheraton West Des Moines Hotel

8/10 Good

"ALL AND ALL IT WAS VERY NICE, AND PRICE WAS RIGHT."

Drury Inn & Suites West Des Moines

10/10 Excellent

"Perfect stay. Nice room, friendly staff, great happy hour and breakfast."

AmericInn by Wyndham Des Moines Airport

8/10 Good

"Stains in toilet"

La Quinta Inn & Suites by Wyndham Des Moines West Clive

10/10 Excellent

"Great breakfast and location"

Motel 6 West Des Moines, IA

8/10 Good

"It was a Motel 6, so expectations weren't high. The room was OK, and it's always nice not to pay extra for a pet. However, the exterior was in pretty bad shape. The sidewalks were cracked an splitting, windows were foggy and dirty."

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 12 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 Clark Tower, Roseman Bridge, 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.

Explore a world of travel with Expedia

Rental cars Des Moines Intl. airport

Book Historic Hotels in Winterset on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Winterset Historic Hotels

Recommended hotels in Winterset