There are plenty of impressive places to stay no matter your destination of choice. Yet, booking a historic hotel or a short-term rental with a storied past—complete with tales of past tenants, centuries-old architecture, or credentials that land a property on a local historical registrar—offers an entirely different level of experience. It creates the ultimate divide between a simple spot to snooze for the night and your next great dinner party conversation piece.
From former artists’ homes and repurposed firehouses to majestic castles and celebrity-studded luxury hotels, travelers increasingly seek out beguiling places around the world to lay their heads. As is frequently the case with older, heritage buildings, some of these properties require a bit of flexibility—such as navigating an outdoor shower or utilizing a less-than-fully-equipped kitchen. Others, however, serve as literal portals to the past, with some locations predating the 16th century while still offering a full suite of modern amenities and high-end luxury.
The following historical hotels and homes have a rich story to tell, and guests get a front-row seat to the living history embedded within their walls.
Still Bend Schwartz House in Wisconsin
Architect Frank Lloyd Wright built a great many incredible spaces for private clients and public institutions, but this specific residence is the very one he contributed to a Life Magazine article back in 1938 as part of a high-profile feature highlighting dream homes. Today, travelers can experience this architectural milestone firsthand.
The four-bedroom estate is exceptionally rich in natural light, featuring sprawling windows highlighted by an entire wall of glass in the 63-foot living room. Each interior space bursts with authentic midcentury furniture and period-accurate decor. Walking through the rooms feels akin to unlocking a new level of a time capsule, transitioning from the deeply nostalgic shag-carpeted primary bedroom to the warm, brick-walled kitchen. While spring, summer, and fall offer lush landscapes across Wisconsin, the outdoor fire pit and relaxing hammock remain deeply inviting even when winter brings a blanket of snow. Nightly rates begin at $841.
The Scriptorium in Glasgow
For travelers planning a road trip through the dramatic landscapes of the Scottish Highlands, this property offers an ideal and atmospheric pit stop. Hidden deep within the stone walls of a former abbey, this unique one-bedroom space once served as the dedicated "writing room" for the resident monks.
The bed is surrounded by striking stained-glass windows that look out across tranquil gardens and toward Loch Ness. Guests enjoy convenient access to the neighboring Highland Club, which houses an impressive indoor swimming pool, a sauna, a tennis court, and various other recreational facilities. While the kitchen and household appliances are modern additions for comfort, original pieces of furniture from the monastery’s past are peppered throughout the rental, including antique wooden benches and historic textiles. Nightly rates begin at $468.
Anemomilos in Greece
For travelers whose daydreams are filled with idyllic al fresco dinners under warm skies, this two-bedroom Greek island home elevates the experience by adding sweeping bird’s-eye ocean vistas to the landscape. Once a working windmill used to grind wheat for flour production, the structure has been thoughtfully transformed to house an outdoor kitchen, a bedroom with panoramic views, and a refreshing outdoor shower.
The scenery visible from the upper-level bedroom is genuinely remarkable, allowing guests to wake up to towering mountain views alongside the endless blue of the ocean. The property’s pool serves as the prime vantage point to take in the Mediterranean sunset before guests retreat to the open-air dining space for a relaxing evening. Nightly rates begin at $224.
Macchiaroli Castle Teggiano in Italy
This historic Airbnb is affectionately known as La Romantica, a moniker that communicates the ambiance of the space immediately. The one-bedroom rental is situated within the oldest section of the broader castle property, which dates back even earlier than the 1400s.
Guests enjoy a private entrance, ancient stone walls, authentic antique Italian furniture, and a traditional fireplace well-suited for warming up a chilly evening. Staying here amounts to a form of time travel, both indoors and out, especially when visitors step outside to explore the surrounding UNESCO World Heritage town of Teggiano. Known for its rich cultural footprint, the town features numerous museums—including the Diocesan Museum, the Herb Museum, and the Museum of Folk Traditions—alongside 13 historic churches. Visitors reside right in the heart of town within easy walking distance of local cafes and medieval architecture. Nightly rates begin at $154.
Historic Firehouse 4 in Washington, DC
Constructed in 1884, this landmark building holds a prominent place in local history as Washington, DC’s first fully African American fire company. The location also holds pop-culture significance as the setting for an episode of the Netflix series Stay Here.
Situated in the historic Shaw neighborhood, the property places guests within walking distance of local cultural institutions like the Howard Theatre, nightlife hubs in Blagden Alley, and prominent live music venues along Eighth Street. The expansive five-bedroom rental retains original architectural details, including the historic fire pole, while the walls are decorated with vintage photography depicting the building’s former personnel. Nightly rates begin at $860.
The Pond House in New York
Guests checking into this two-bedroom forest-view retreat step directly into the creative world of celebrated painter Reginald Marsh. A picturesque pond anchors one side of the property, and the expansive lawns are landscaped deliberately for long, contemplative post-dinner strolls.
Despite its secluded natural ambiance, the property sits just a short walk from the center of Woodstock, granting easy access to local restaurants, bars, cafes, and shops. The home even features a private waterfall that borders a public nature preserve open to exploration. Indoors, a robust personal library and a wood-burning stove provide cozy retreats on brisk autumn and winter evenings, while the full kitchen and outdoor dining space cater to warm-weather culinary pursuits. Nightly rates begin at $619.
The Luxury Palace Hotel in Madrid
Centrally located in Madrid’s historic Plaza de las Cortes, the landmark Palace Hotel reopened its doors following an extensive, property-wide renovation project. The two-year modernization effort touched nearly every corner of the historic hotel, including the grand main lobby, updated dining spaces, and 470 guest rooms, all featuring reimagined interiors designed by Lázaro Rosa-Violán.
Dating back to its original 1912 debut, The Palace has hosted legendary cultural figures over the decades, including Salvador Dalí and Ernest Hemingway. It also holds the distinction of being credited as the first hotel in Spain to feature private toilets within every guest quarter. Today, visitors experience pieces of the hotel’s storied past through a contemporary design lens. Custom-designed bespoke fixtures mingle with vintage tapestries and modern Joan Miro prints inside La Cúpula Restaurant. Updated bathrooms feature rich red marble stone touches, while the central location places art enthusiasts just a five-minute walk from the Thyssen-Bornemisza National Museum, the Prado Museum, and El Retiro Park. Nightly rates begin at $1,060.
The Waldorf Astoria in New York
The history of the Waldorf Astoria runs exceptionally deep within the fabric of New York City hospitality. Originally designed in 1893 as two side-by-side hotels built by feuding family members, the combined property was eventually demolished in 1929 to clear the land for the construction of the Empire State Building.
The hotel reopened at its current Park Avenue location in 1931, immediately breaking global records as the largest and tallest hotel in the world at the time. Its distinctive Art Deco architecture and lavish interiors quickly drew the attention of global royalty, prominent politicians, and international celebrities. The illustrious guest book over the decades has included luminaries such as Nikola Tesla, Winston Churchill, Zsa Zsa Gabor, and members of the presidential administration. Following an extensive multi-year closure dedicated to comprehensive historical renovations, the legendary property is preparing for a grand reopening season. Nightly rates begin at $1,221.
The Balmoral Hotel in Edinburgh
A towering architectural landmark in the Scottish capital, the Balmoral is universally recognized for its iconic 190-foot clock tower—which has been intentionally set three minutes fast every day of the year except New Year’s Eve since the hotel opened in the early 1900s. The property also holds a notable place in modern literary history; author J.K. Rowling finished writing the final installment of the Harry Potter series on January 11, 2007, while staying in Suite 552. The room is now commemorated with a custom owl door knocker and an in-room bust of the Greek god Hermes signed by the author.
Guests frequently return for the sprawling, comfortable bedrooms, many of which frame picturesque, postcard-worthy views of Edinburgh Castle. The accommodations showcase a blend of cozy traditional design, contemporary wallpaper prints, neutral plaid textiles, and ultra-soft wool bed covers. Nightly rates begin at $399.
The Carlyle Rosewood Hotel in New York
Nestled on 76th Street just off Madison Avenue, the Carlyle first opened its doors to the public in 1930. In the decades since, sitting presidents, foreign royalty, and major cinematic stars have consistently sought refuge within its hallowed walls.
The property’s interiors blend sophisticated Art Deco touches with classic New York eclecticism, utilizing a layered mix of vintage-inspired furniture silhouettes, contemporary art pieces, and dramatic chandeliers. One of the hotel’s most enduring attractions for both local residents and overnight guests is the iconic Bemelmans Bar, which is outfitted with whimsical, hand-painted wall murals created by Madeline author and illustrator Ludwig Bemelmans. Nightly rates begin at $1,323.
Hotel Figueroa in Downtown Los Angeles
Marking a major milestone, Hotel Figueroa celebrates its centennial anniversary, honoring a century of hospitality in Downtown Los Angeles. The property was originally financed, owned, and operated by the Young Women’s Christian Association (YWCA) to function as a secure haven for solo female travelers during an era when most commercial hotels prohibited unaccompanied women from checking in without a male chaperone.
Today, Spanish Revival design influences flourish throughout the refreshed public spaces and rooms, featuring curated art created exclusively by female artists, sophisticated tilework, and modern furnishings. Guests can swim in the landmark coffin-shaped outdoor pool dating back to the 1920s while surrounded by mature, decades-old cacti, enjoying craft cocktails from the poolside bar alongside Italian culinary classics served at the in-residence restaurant. Nightly rates begin at $129.
Brown’s Rocco Forte Hotel in London
Widely recognized as London’s oldest continuously operating luxury hotel, Brown’s has undergone careful updates—including glossy marble bathrooms, vibrant textiles, and mahogany walk-in closets—that breathe new life into the historic stay. At the same time, careful preservation of the original architecture, visible in the stained-glass windows, untouched entryways, and wrought-iron façade detailing, maintains a tangible bond to the building’s storied heritage.
Situated in the upscale Mayfair neighborhood, the property has a long literary pedigree, having hosted legendary authors such as Rudyard Kipling, Bram Stoker, Agatha Christie, and Stephen King, the latter of whom notably outlined his bestselling thriller Misery during a visit. Proximity to cultural landmarks like Buckingham Palace and Hyde Park ensures guests remain well-situated to explore the city. Nightly rates begin at $966.
