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Frank Lloyd Wright’s Schwartz House in Two Rivers, WI
Photograph: Courtesy Airbnb

11 historic homes near Chicago that you can rent on Airbnb

Marvel at the architecture, old-school details and quirky charm of these historic homes for rent on Airbnb

Written by
Danielle Goldstein
Annalise Mantz
Lola Christina Alao

Not everyone likes the modern apartment vibe, some of you might prefer apartments with an antique feel, original light fixtures and real fireplaces. If that's you, consider one of these historic homes nearby to Chicago for your next trip. So whether you're looking for a smaller property on a budget, or you want to go all out and splurge a bit, this is the list for you. We can't forget that mainline Chicago is stunning and well worth a visit. But sometimes, it's good to have a change – a bit of peace and quiet. So read on for our top recommendations of historic Airbnbs near Chicago.

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Historic homes near Chicago on Airbnb

The Castle on Roanoke in Peoria, IL
Photograph: Courtesy Airbnb

1. The Castle on Roanoke in Peoria, IL

Located in the Randolph-Roanoke Historic District of Peoria, this regal structure stands out among a sea of classic Victorians. The stone exterior and prominent turret give way to an updated interior with two bedrooms, two bathrooms and a fully equipped kitchen. Plus, it's usefully located only a short distance from some major attractions, including Peoria Civic Center, the riverfront and the warehouse district.

Frank Lloyd Wright’s Schwartz House in Two Rivers, WI
Photograph: Courtesy Airbnb

2. Frank Lloyd Wright’s Schwartz House in Two Rivers, WI

This home was actually originally designed by legendary architect Frank Lloyd Wright for a LIFE magazine feature in 1938. And now, it's available to rent in AirBnb. You mght also recognise it from Netflix's The World's Most Amazing Vacation Rentals. Frank Lloyd Wright wrote in Life Magazine about the plan, “ life is unlike any other in the world and I think this plan recognizes it for pretty much what it is — a little private club — with special privacies, ultra conveniences and style all the while." So that's exactly what you can expect. It's a huge four bedroom, with a fully equipped kitchen and wood finishes. What a dream.  

The Pullman Train Car Constitution in Plano, IL
Photograph: Courtesy Airbnb

3. The Pullman Train Car Constitution in Plano, IL

If the fact that this Airbnb is a 180,000-pound antique train car doesn’t quite convince you to make a reservation, consider this: it might be your only chance to sleep in the same room as two US presidents. How? Because the train car Constitution served as the 1900s version of Air Force One for Presidents Warren G Harding and Woodrow Wilson. The carefully renovated car includes the original four staterooms, an observation deck, a dining room and a galley, plus a master bedroom, a bathroom and two large living rooms with fireplaces that were added later.

Historic Church Home in Logan Square
Photograph: Courtesy Airbnb

4. Historic Church Home in Logan Square

After taking in the lofted ceilings, arched doorways and belltower of this home, it’s no surprise to learn it was converted from a church built in 1888. The expansive space can sleep up to 13 people and features intriguing details like inlaid wooden crosses, antique typewriters and stunning religious murals. As historic homes on Airbnb go, it’s pretty heavenly.

Hamilton House in Whitewater, WI

5. Hamilton House in Whitewater, WI

Built in the 1800s, Hamilton House is a stunning example of Italianate architecture, which was saved from demolition in the 1980s by the town's residents and businesses. It's now run by Gloria Marie, who rents out its eight bedrooms to those visiting historic Whitewater. Each room is sympathetically decorated in a Victorian style and breakfast is included. They also host wine tastings in the parlour, with Wisconsin cheeses, and local activities include biking and hiking in the Kettle Moraine.

Charming Farmhouse near Lake Michigan
Supplied by Airbnb

6. Charming Farmhouse near Lake Michigan

This peaceful getaway with great 1930s charm is like something out of a magazine. It's perfect for a big family or a big friendship group, as it has five bedrooms and three bedrooms. You definetely won't struggle for space here. In the master bedroom, you'll find a heart shaped jetted tub to give you that peace and solitude your heart desires. There is also a games room full of vintage games and Lewis Farm Market nearby. And it's not far from Lake Michigan, so there are limitless possibilities for day trips.

1800s Home on Indiana’s Historic National Road in Greenfield, IN
Photograph: Courtesy Airbnb

7. 1800s Home on Indiana’s Historic National Road in Greenfield, IN

This white-paneled house has a long history of hosting travelers: in the 1800s it operated as a stagecoach inn. The renovated interior features a few unique architectural elements, including a sliding barn door and intricate built-ins. It’s pet-friendly too, so you can bring your bestie along. Be sure not to miss the back building, which actually features an outdoor bar. So, next round on you?

Established Cabin on the Rock River in Oregon, IL
Photograph: Courtesy Airbnb

8. Established Cabin on the Rock River in Oregon, IL

The rustic cabin on this pristine stretch of riverfront property looks much the same as it would have in 1907, though it's been outfitted with electricity, hot water and a working kitchen since then. Still, it’s the perfect getaway if you’re looking to connect with nature without sleeping in a tent. Whether you hike the nearby Lowden-Miller Forest, kayak the Rock River or just nap in one of the hammocks, you’re in for a treat.

Victorian Charm in Watertown, WI
Airbnb Victorian house Watertown Wisconsin

9. Victorian Charm in Watertown, WI

Calling all antique home lovers, this Airbnb with Victorian charm has your name written all over it. Nicknamed "Belle Maison", meaning beautiful house, it's newly restored, with two bedrooms and two bathrooms. And the best thing is that one bathroom has its original claw foot tub. You'd be just a block from Main Street, with plenty of shops and restaurants within walking distance. And for when you want a bit of nature and scenic views, take a visit to the beautiful Rock River which is also nearby. 

Old Family Farm in Sturgeon Bay, WI
Photograph: Courtesy Airbnb

10. Old Family Farm in Sturgeon Bay, WI

This historic farm on 100 acres of farmland has been in the same family for generations—116 years, to be exact. Though it's been updated with central air conditioning and other modern conveniences, the home features the original hardwood floors and decades of family art. The spacious property offers plenty of opportunities for outdoor fun, too. Visitors might enjoy hiking, birdwatching, biking, snowmobiling or roasting marshmallows at the fire pit.

Looking for more getaway ideas?

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