12 historic hotels and vacation rentals

There are numerous impressive places to stay around the world, regardless of where your travels may take you. However, booking a historic hotel or Airbnb rental with a rich history—such as past tenants, centuries-old architecture, or any other factor that might earn a property a place on a local list—is the key difference between merely sleeping and having an unforgettable experience for your next dinner party.

From former artists' homes and firehouses to castles and celebrity-studded hotels, we have carefully selected several intriguing accommodations to rest your head at night.

Some older buildings require additional flexibility, like an outdoor shower or a kitchen that may not be fully equipped. Meanwhile, others offer a window into the past, with some of these spots dating back to the 16th century, and feature ample amenities and luxurious touches. The following historic hotels and homes possess a fascinating tale, and guests get an exclusive front-row seat.

Situated in Wisconsin, the Still Bend Schwartz House offers shared beach access, an in-unit washer and dryer, a sound system, an indoor fireplace, and a fire pit. Designed by Frank Lloyd Wright, this four-bedroom estate showcases midcentury furniture and decor, with each room revealing a new level of a time capsule—from the shag-carpeted primary bedroom to the brick-walled kitchen.

While spring, summer, and fall are beautiful times to visit, the fire pit (and hammock) outside remains inviting even in winter and snow. The nightly rate is $841.

In Glasgow, the Scriptorium provides a perfect stop on a road trip through the Highlands. Housed in a former abbey, this one-bedroom space was once the "writing room" for the monastery. Surrounded by stained glass windows overlooking the gardens and Loch Ness, guests have access to the neighboring Highland Club, which features an indoor pool, sauna, tennis court, and more. Although the kitchen and appliances are recent additions, original furniture pieces are scattered throughout the rental. The nightly rate is $468.

For those seeking a beachside retreat, the Anemomilos in Greece is a two-bedroom home with a pet-friendly policy. Once a windmill, it now boasts an outdoor kitchen, a bedroom with a view, and an outdoor shower. Guests can enjoy ocean vistas, a pool, an outdoor dining space, and breathtaking mountain views from the top bedroom. The nightly rate is $224.

La Romantica, or Macchiaroli Castle in Teggiano, Italy, is another fascinating choice. Dating back earlier than the 1400s, this one-bedroom rental is situated in the oldest section of the property, featuring private entrance, ancient stone walls, antique Italian furniture, and a fireplace. Guests can explore the surrounding UNESCO heritage town, Teggiano, known for its museums and 13 churches. The nightly rate is $154.

Built in 1884, Historic Firehouse 4 in Washington, DC, was once the city's first fully African American fire company and served as a set for a Netflix show. Located in the Shaw neighborhood, a historic district, this five-bedroom rental features the original fire pole and photographs of previous tenants. With central location, pet-friendly policy, air conditioning, private parking, and historic decor, guests can enjoy the fire pit and a wood-burning stove on chilly nights. The nightly rate is $860.

In New York, The Pond House is a two-bedroom getaway nestled amidst forest views. With a pond as one side of the property, expansive lawns are perfect for post-dinner strolls. Despite its secluded feel, it's a brief walk to the center of Woodstock, offering restaurants, bars, cafes, and shops. A private waterfall borders a public preserve, offering guests the chance to explore.

The library provides a relaxing indoor space, while the wood-burning stove on chilly nights makes the outdoor dining space ideal for summertime grilling. The nightly rate is $619.

The Luxury Palace Hotel in Madrid offers a central location in Plaza de las Cortes, just steps away from trendy bars and restaurants. This historic hotel reopened its doors in 2025, unveiling property-wide updates following a two-year renovation project with designer reimagination of interiors. With 470 rooms, an updated main lobby, and dining accommodations, guests can enjoy Aqua di Parma and Byredo toiletries during their stay.