This Wisconsin Airbnb Is Like Stepping Onto the Set of Letters to Juliet

It sometimes feels cliché, but after visiting more than 30 countries, I still say that Italy is my favorite country to visit. I believe my love affair with pizza and red wine stemmed from watching the 2010 rom-com Letters to Juliet. While Italy may be a bit far for a weekend adventure, this Tuscany-like castle and vineyard vacation rental in Cleveland, Wisconsin, is a good substitute.

If you're like me, you fell for the cinematic wine fields and architecture scattered throughout Letters to Juliet. Whether it was Vanessa Redgrave wandering Tuscany in search of her long-lost soulmate or Amanda Seyfried's character discovering the secrets of romance, the movie truly captured the heart of Bel Paese.

But why travel thousands of miles when you can find a piece of Italy right here in the Midwest? A stay in this small town's picturesque vacation rental offers all the Instagram-worthy shots of a European castle and vineyard. Opened in 2022, the rental is perfect for a romantic getaway or a girls' trip filled with good wine and even better company.

Before even entering the property, you'll notice an ornate front door. This arched door was handcrafted by a local professional Italian doormaker who was about to move back to Italy. The dining room is another feat of design with its large wooden windows and table made out of a 1914 John Deere two-bottom plow. 

The kitchen’s hanging lights even came from an 1800s church in Plymouth, Wisconsin. You’ll also notice a massive sailfish hanging there. While it can’t be proved, legend has it that this sea creature used to belong to Ernest Hemingway.

In addition to the four bedrooms and two and a half baths that house up to 12 guests, the home offers a few uniquely themed rooms. One such room is the piano room. Sit down on the ivory and enjoy playing the piano, which was a retirement gift from General MacArthur to his personal limo driver.

Next, grab a glass and explore the wine hall. In addition to the wine bottles and 32 whiskey barrels decorating the space, it showcases a 1902 potato plow chandelier. Plus, the door to the wine cellar is made from an original gun room door of a WWII Battleship.

In addition to these quirky rooms, guests will enjoy access to a home theater and golf simulator. An outdoor hot tub is open to guests on the beautiful back patio, as well. The home offers an ornate kitchen, pool table, fire pit, basketball court, and a whole lot more. Guests can even utilize the space for larger events like weddings.

If you’re looking for a one-of-a-kind getaway or a memorable venue for your next big event, this incredible property has it all. From the distinctive historical touches to the impressive amenities, every corner of this home offers something special for its guests. Even if you've been to Italy a hundred times, you'll feel like you're strolling the vineyards with Franco Nero in Letters to Juliet. What other spots in Wisconsin remind you of the sets of your favorite films? Let us know by filling out our nomination form.