Italy isn’t just a country you visit. It’s a country you live, breathe, and, if you’re lucky, sleep in. With its wealth of history stretching back thousands of years, Italy offers travelers the rare opportunity to stay not just near history, but in it. From restored castles and centuries-old palazzos to monasteries, watchtowers, and even ancient caves, Italy’s historical buildings have been thoughtfully converted into accommodations that blend the charm of the past with modern comforts.

Throughout cities and countryside alike, Italy is filled with palazzi – grand homes once owned by noble families. Many have been carefully restored and converted into boutique hotels, B&Bs, or private guest rentals. Staying in one means immersing yourself in frescoed ceilings, antique furnishings, and ornate courtyards.

Palazzo Guadagni in Florence is a 16th-century palace with arched loggias and views over the Oltrarno district. Villa Spalletti Trivelli in Rome is an aristocratic residence turned luxury hotel with period décor and a private garden.

Across regions like Tuscany, Umbria, and the Veneto, many medieval castles have been transformed into atmospheric accommodations. Some are luxurious resorts, others charming agriturismi, but all offer a sense of timelessness and storybook allure.

Castello di Petroia in Umbria is a 10th-century castle surrounded by forests and farmland while Castello di Velona in Tuscany is a hilltop fortress near Montalcino with its own thermal spa.

If you’re seeking peace, simplicity, and spiritual resonance, Italy’s ancient monasteries and convents provide a unique retreat. Some offer minimalist lodging with religious ambiance, while others have been renovated into boutique spiritual hotels or wellness retreats.

In Puglia, the iconic conical-roofed trulli, once humble peasant homes, have become stylish vacation rentals. Meanwhile, in Matera, the prehistoric Sassi cave dwellings have been reinvented as sophisticated hotels that preserve the cave’s natural textures while adding luxury touches.

For the truly adventurous traveler, Italy offers overnight stays in medieval watchtowers, lighthouses, and historic mills. Many of these are part of regional restoration efforts that allow guests to help preserve heritage just by staying there.

Torre di Scopello in Sicily is a 16th-century coastal tower with breathtaking views. Faro Capo Spartivento in Sardinia is a restored lighthouse with luxury suites and sea access.

If you are considering booking a historical stay in Italy, book early, especially in spring and fall, when demand is high. Check accessibility as historic buildings often have stairs and no elevators. Read up on the history of where you're staying. It adds so much depth to the experience. And, don’t expect cookie-cutter rooms! Each will likely be unique, which is part of the charm.