The Ultimate Guide to Booking Historic Hotels and Storied Stays Around the World

There are plenty of impressive accommodations out there, no matter your destination of choice. But booking a historic hotel or Airbnb rental with a storied past—tales of former tenants, centuries-old architecture, or whatever else might land a property on a local historical registrar—is the difference between a simple spot to snooze at night and your next great dinner party conversation.

From former artists’ homes and historic firehouses to grand castles and celebrity-studded legendary hotels, travelers are increasingly seeking out beguiling places around the world to lay their heads at night. As is often the case with older, heritage buildings, some of these locations require a bit of flexibility from guests—say, an outdoor shower or a less-than-fully-equipped kitchen—while others offer a literal portal to the past, with some spots on this roster predating the 16th century while remaining fully rich with modern amenities and luxury.

The following historical hotels and homes have an incredible story to tell, and modern guests get a front-row seat to experience that history firsthand.

Still Bend Schwartz House in Wisconsin

Architect Frank Lloyd Wright built a lot of incredible spaces for clients throughout his legendary career, but this particular property is the very one he contributed to a Life Magazine article back in 1938 as part of a high-profile feature highlighting modern dream homes. Located in Wisconsin, the four-bedroom estate is exceptionally bright and airy, full of expansive windows, including a dramatic 63-foot living room featuring an entire wall of glass looking out at the landscape.

Each space inside the house is bursting with midcentury furniture and decor, making a walk through the rooms feel like unlocking a new level of a time capsule. Highlights range from the shag-carpeted primary bedroom to the authentic brick-walled kitchen. While spring, summer, and fall are widely considered beautiful times to visit the scenic Wisconsin countryside, the outdoor fire pit and comfortable hammock remain deeply inviting even when winter arrives and snow blankets the grounds. Nightly rates begin at $841.

The Scriptorium in Glasgow

For travelers planning a road trip through the breathtaking Scottish Highlands, this unique stay serves as an ideal and atmospheric pit stop. Hidden away in the depths of a former abbey, this one-bedroom space originally functioned as the dedicated "writing room" for the monastery. The bedroom itself is surrounded by magnificent stained-glass windows that look out over tranquil gardens and the legendary Loch Ness, famed for its elusive monster.

Guests staying here enjoy full access to the neighboring Highland Club, which houses an incredible indoor pool, a soothing sauna, a premier tennis court, and a wide array of other upscale amenities. While the kitchen and modern appliances are newer additions integrated for convenience, visitors will still find original pieces of furniture from the historic space peppered throughout the rental, including a rustic wooden bench here and a vintage tapestry there. Nightly rates begin at $468.

Anemomilos in Greece

For travelers whose daydreams are constantly filled with leisurely al fresco dinners under the stars, this two-bedroom Greek home elevates the experience by adding breathtaking, bird’s-eye ocean vistas to the scene. Once functioning as a traditional windmill that ground wheat for flour production, the structure has been cleverly repurposed to house an outdoor kitchen, a bedroom with an extraordinary view, and a refreshing outdoor shower.

The views from the top-floor bedroom are truly remarkable, allowing guests to wake up to sweeping mountain vistas and the deep blue ocean beyond. The property’s private pool serves as the ultimate vantage point to take in the brilliant sunset before retreating to the open-air dining space for a wonderful evening of food and conversation. Nightly rates begin at $224.

Macchiaroli Castle Teggiano in Italy

This historic Airbnb is officially known as La Romantica, a moniker that tells visitors everything they need to know about its romantic, medieval ambiance. The one-bedroom rental is situated directly within the oldest section of the property, which dates back earlier than the 1400s. Guests enjoy a private entrance, ancient stone walls, authentic antique Italian furniture, and a massive fireplace that is ideal for fighting off a chilly night.

Staying here feels like genuine time traveling, both indoors and out, especially when guests step outside to explore the surrounding UNESCO World Heritage town of Teggiano. Known extensively for its rich cultural footprint, the town boasts numerous museums—including the Diocesan Museum, the Herb Museum, and the Museum of Folk Traditions—alongside 13 historic churches. Visitors at this one-bedroom retreat are located right in the middle of town and within easy walking distance of everything they could possibly need, ensuring that slipping out for a quick dinner, a morning coffee at a local café, or a sunset stroll past medieval architecture is always effortless. Nightly rates begin at $154.

Historic Firehouse 4 in Washington, DC

Built in 1884, this remarkable structure was originally Washington, DC’s first fully African American fire company and later served as the vibrant television set for an episode of the Netflix home-renovation series Stay Here. Situated in the heart of the Shaw neighborhood, a historically rich district in the nation’s capital, guests are within steps of legendary local culture, including live plays at the Howard Theatre, craft drinks in Blagden Alley, and live music at the Eighth Street Lounge and Bar.

The expansive five-bedroom rental retains authentic historical elements, including the original fire pole, while vintage photography of previous tenants decorates the walls to honor the building’s profound heritage. Nightly rates begin at $860.

The Pond House in New York

Travelers can step straight into the creative world of renowned painter Reginald Marsh by booking a stay at this two-bedroom woodland getaway framed by lush forest views. A peaceful pond anchors one side of the property, and the expansive lawns are thoughtfully landscaped with long, contemplative post-dinner strolls in mind.

Despite feeling wonderfully secluded, the home is just a short, pleasant walk to the center of Woodstock, New York, putting local restaurants, bars, cafes, and independent shops within easy reach. While the property is not directly adjacent to a national park, a private waterfall on the grounds directly borders a public nature preserve that is wide open for exploration. Indoors, a well-stocked library pulls guests back inside, alongside a cozy wood-burning stove for chilly autumn and winter nights. The outdoor dining space shines during the summer for grilling, though the fully equipped indoor kitchen is equally delightful to work in. Nightly rates begin at $619.

The Luxury Palace Hotel in Madrid

Centrally located in Madrid’s iconic Plaza de las Cortes, the historic Palace Hotel officially reopened its doors to unveil sweeping property-wide updates—including a completely revitalized main lobby, upgraded dining accommodations, and 470 redesigned rooms. These enhancements are the culmination of a massive two-year renovation project featuring reimagined interiors by acclaimed designer Lázaro Rosa-Violán. Dating back to its original opening in 1912, The Palace has hosted legendary historical figures such as Salvador Dalí and Ernest Hemingway, and it holds the distinction of being the very first hotel in Spain to feature private toilets in its guest quarters.

Today, guests can appreciate pieces of the property’s storied past through a fresh, contemporary lens. Surrounded by bespoke fixtures custom-designed by Rosa-Violán, vintage tapestries hang alongside contemporary Joan Miró prints inside La Cúpula Restaurant. Within the inviting suites, updated bathrooms feature original red marble stone. Just a five-minute walk away, art aficionados can spend long hours wandering through the Thyssen-Bornemisza National Museum and the Prado Museum, or take a peaceful stroll through El Retiro Park.

"The hotel staff at The Palace are some of the friendliest I’ve encountered," notes commerce editor Audrey Lee. "You’ll definitely want to stop by La Cúpula during your trip for an afternoon drink and some bites from the stylish tapas menu. If it’s the right time of day, the room becomes drenched in sunlight through the dome-shaped stained glass ceiling." Nightly rates begin at $1,060.

The Waldorf Astoria in New York

The history of the world-famous Waldorf Astoria runs exceptionally deep within New York City lore. Originally designed in 1893 as two side-by-side hotels built by feuding family members, the collective property was eventually demolished in 1929 to clear land for the construction of the Empire State Building. It triumphantly reopened at its current Park Avenue location in 1931, immediately breaking architectural records as the largest and tallest hotel in the entire world at the time.

Its striking Art Deco architecture and lavish interiors quickly captured the attention of royalty, international celebrities, and prominent politicians. The distinguished guest book includes monumental figures such as Nikola Tesla, Winston Churchill, Zsa Zsa Gabor, and the Obama family, among many others. Following a prolonged closure for extensive, meticulous renovations, the legendary property is planning a grand re-opening. Nightly rates begin at $1,221.

The Balmoral Hotel in Edinburgh

A towering historic landmark in the Scottish capital, the Balmoral is globally recognized for its iconic 190-foot clock tower—which is famously set three minutes fast year-round, except for a brief reset on New Year’s Eve—that has defined the Edinburgh skyline since the early 1900s. Literary history was cemented here when J.K. Rowling famously finished the final manuscript of the Harry Potter series on January 11, 2007, inside Suite 552. That milestone is now permanently commemorated with a special owl door knocker and an in-room bust of the Greek god Hermes bearing Rowling’s personal signature.

"The Balmoral does rest and relaxation like no other through comforting amenities, charming interiors, and hearty cuisine," shares shopping editor Audrey Lee. "After a long day of taking in Edinburgh’s historic sights, there was nothing I looked forward to more than the treats from turndown service and a long soak in the glossy marble tub." Guests frequently return for the sprawling, well-appointed bedrooms, some of which frame picturesque, postcard-worthy views directly across to Edinburgh Castle. The interiors showcase cozy, traditional design layered with contemporary wallpaper prints, neutral plaid furnishings, and ultrasoft wool bed covers. Nightly rates begin at $399.

The Carlyle Rosewood Hotel in New York

Nestled discreetly on 76th Street just off Madison Avenue, the Carlyle first welcomed guests in 1930. In the decades since, presidents, foreign royalty, and Hollywood movie stars have consistently sought refined refuge within its hallowed walls.

"You can have breakfast next to Daniel Patrick Moynihan or Tom Ford," legendary Los Angeles–based designer and AD100 Hall of Famer Michael S. Smith once observed. "It’s like a big hotel in a small town, the grande dame of New York."

The sophisticated interiors effortlessly blend classic Art Deco touches and New York eclecticism with traditional architecture, achieved through a layered mix of vintage-inspired furniture silhouettes, contemporary artwork, and dramatic chandeliers. One of the hotel’s top cultural attractions for both local residents and overnight guests is the world-famous Bemelmans Bar, which is outfitted with whimsical, hand-painted wall murals created by Madeline author and illustrator Ludwig Bemelmans. While a classic martini remains a failsafe order, visitors can also sample specialty drinks like the namesake Madeline’s Vesper or Bobby’s Manhattan, a heartfelt homage to late cabaret singer Bobby Short, who was a longtime musical fixture of the adjacent Café Carlyle. Nightly rates begin at $1,323.

Hotel Figueroa in Downtown Los Angeles

Marking a major milestone, Hotel Figueroa celebrates its 100th anniversary. The Young Women’s Christian Association (YWCA) originally financed, owned, and operated the Downtown Los Angeles fixture with a profoundly progressive mission: to function as a safe, reliable haven for solo female travelers. The property proudly allowed unaccompanied women to check in without requiring a male chaperone, a progressive policy that most hotels strictly prohibited during the era.

Today, elegant Spanish Revival design influences flourish throughout the refreshed space, featuring carefully curated art created exclusively by female artists, sophisticated tilework, and modern furnishings. Guests can take a refreshing dip in the historic, coffin-shaped swimming pool dating back to the 1920s while surrounded by towering, 50-year-old cacti. Afterward, visitors can enjoy craft cocktails and light bites from the poolside bar, La Casita, or head inside for a substantial meal at the on-site restaurant Florence by the Water, which serves up comforting Italian classics. Nightly rates begin at $129.

Brown’s Rocco Forte Hotel in London

Widely recognized as London’s oldest luxury hotel, thoughtful modern updates—such as glossy marble bathrooms, vibrant textiles, and spacious mahogany walk-in closets—have breathed exciting new life into this historic Mayfair stay. At the same time, respectful homages to the original architecture, visible in the stained-glass windows, untouched entryways, and intricate wrought-iron facade detailing, maintain an unbroken bond to the property’s rich heritage.

"You might think the main attraction of Brown’s is its proximity to landmarks like Buckingham Palace and Hyde Park, but it’s actually the inviting staff and dapper design that make this stay more like a home than a stopover," Lee notes.

Past literary guests of note who found inspiration within these walls include Rudyard Kipling, Bram Stoker, Agatha Christie, and Stephen King; notably, King outlined portions of his bestselling thriller Misery during one of his stays. Situated in the upscale Mayfair neighborhood, the hotel places world-class shopping and top London cultural institutions right at the doorstep to ensure any travel itinerary stays fully engaged. Nightly rates begin at $966.