There are plenty of impressive accommodations available for travelers, regardless of the destination of choice. However, booking a historic hotel or a unique rental property with a storied past—complete with tales of former tenants, centuries-old architecture, or official recognition on a local historical registrar—represents the difference between a simple place to sleep at night and a memorable conversation starter for your next dinner party.
From former artists’ homes and converted firehouses to medieval castles and celebrity-studded grand hotels, a curated selection of properties around the world offers travelers a distinct place to lay their heads at night. As is often the case with older buildings, some of these historic stays require a degree of flexibility from guests, such as navigating an outdoor shower or utilizing a kitchen with fewer modern appliances. Conversely, other destinations serve as a direct portal to the past, with some properties predating the 16th century while still providing modern amenities and luxury.
These historical hotels and residential homes possess a rich narrative to share, and guests are given a front-row seat to experience that history firsthand.
Still Bend Schwartz House in Wisconsin
Architect Frank Lloyd Wright designed a multitude of incredible spaces for clients throughout his legendary career, but the Still Bend Schwartz House is the very property he contributed to a Life Magazine article back in 1938 as part of a special feature highlighting dream homes. Situated in Wisconsin, the four-bedroom estate is heavily defined by its extensive use of glass. The 63-foot living room features an entire wall of windows, and every space within the house is vibrant with midcentury furniture and decor.
Walking into each room feels akin to unlocking a new level of a time capsule, transitioning from the shag-carpeted primary bedroom to the distinct brick-walled kitchen. While spring, summer, and fall offer scenic backdrops for a visit to Wisconsin, the outdoor fire pit and hammock remain inviting even when winter brings snow to the region. Stays at this architectural landmark start from $841 per night, with perks including shared beach access, an in-unit washer and dryer, a sound system, an indoor fireplace, and an outdoor fire pit.
The Scriptorium in Glasgow
Hidden deep within the architecture of a former abbey, this unique one-bedroom space once served as the "writing room" for the monastery, making it an ideal pit stop on a road trip through the Scottish Highlands. The bed is surrounded by striking stained-glass windows that look out over the property’s gardens and Loch Ness.
Guests staying at the Scriptorium are granted access to the neighboring Highland Club, which houses an indoor swimming pool, sauna, tennis court, and other recreational facilities. While the kitchen and appliances are newer additions to accommodate modern needs, original elements of the space remain peppered throughout the rental, including antique wooden benches and historic tapestries. Rates begin from $468 per night, accompanied by amenities such as a badminton net, steam room, gym, BBQ grill, and an EV charger.
Anemomilos in Greece
For travelers whose daydreams involve al fresco dining, this two-bedroom Greek home elevates the experience by incorporating bird’s-eye ocean vistas into the surrounding landscape. Once a working windmill used to grind wheat for flour production, the structure now encompasses an outdoor kitchen, a bedroom with panoramic views, and an outdoor shower.
The vistas from the top-floor bedroom offer an impressive backdrop, allowing guests to wake up to views of the mountains and the open sea beyond. The property’s pool serves as a primary vantage point for taking in the sunset before guests retreat to the open-air dining space. Stays start from $224 per night, with pet-friendly accommodations, a patio, free parking, a pool, and an outdoor shower included among the perks.
Macchiaroli Castle Teggiano in Italy
Known locally as La Romantica, this historic Airbnb is located within the oldest section of a property that dates back earlier than the 1400s. The one-bedroom rental features a private entrance, ancient stone walls, antique Italian furniture, and an indoor fireplace designed to warm up chilly evenings.
The location allows guests to experience a form of time travel, both within the confines of the castle walls and outside when exploring the surrounding UNESCO heritage town of Teggiano. Known for its medieval architecture, numerous churches, and museums—including the Diocesan Museum, the Herb Museum, and the Museum of Folk Traditions—the town places guests within walking distance of local cafes, restaurants, and historical sites. Rates start from $154 per night, with perks including pet-friendly policies, Wi-Fi, luggage drop-off, radiant heating, and a fireplace.
Historic Firehouse 4 in Washington, DC
Built in 1884, this Washington, DC property holds the distinction of being the city’s first fully African American fire company and even served as a filming location for the Netflix series Stay Here. Situated in the historic Shaw neighborhood, the five-bedroom rental places guests close to local cultural attractions such as the Howard Theatre, Blagden Alley, and nearby music lounges.
The interior retains distinctive historical features, including the original fire pole, while photography depicting previous tenants decorates the walls. Stays at this location start from $860 per night, with amenities featuring pet-friendly policies, air conditioning, private parking availability, a fireplace, and historic decor.
The Pond House in New York
Guests staying at this two-bedroom New York getaway with forest views step directly into the artistic world of painter Reginald Marsh. A tranquil pond anchors one side of the property, and the expansive lawns are landscaped to accommodate post-dinner strolls. Despite its secluded atmosphere, the house is located a short walk from the center of Woodstock and its array of restaurants, bars, cafes, and shops.
A private waterfall borders a public preserve open to exploration, while the indoor library and wood-burning stove provide inviting spaces during cooler weather. The property features both an outdoor dining space for summertime grilling and a fully equipped indoor kitchen. Rates start from $619 per night, with perks such as shared beach access, a sound system, exercise equipment, and a fire pit.
The Luxury Palace Hotel in Madrid
Centrally located in Madrid’s Plaza de las Cortes, the historic Palace Hotel reopened its doors to unveil property-wide updates encompassing its main lobby, dining accommodations, and 470 rooms. The renovations are the result of a two-year project featuring reimagined interiors by designer Lázaro Rosa-Violán. Dating back to 1912, the Palace has hosted notable historical figures such as Salvador Dalí and Ernest Hemingway, and it holds the distinction of being the first hotel in Spain to feature private toilets in its quarters.
Today, visitors can experience the property’s historic legacy through a contemporary lens. Surrounded by bespoke fixtures custom-designed by Rosa-Violán, vintage tapestries hang alongside contemporary Joan Miro prints in La Cúpula Restaurant. Updated bathrooms within the suites feature original red marble stone. Situated just a five-minute walk from the Thyssen-Bornemisza National Museum, the Prado museum, and El Retiro Park, the hotel offers a central base for art enthusiasts. Stays start from $1,060 per night, with amenities including a central location, a 24-hour fitness center, balcony access, and luxury toiletries.
The Waldorf Astoria in New York
The history of the Waldorf Astoria spans well over a century. Originally designed in 1893 as two side-by-side hotels built by feuding family members, the combined property was demolished in 1929 to clear land for the construction of the Empire State Building. It reopened at its current Park Avenue location in 1931, setting records at the time as the largest and tallest hotel in the world.
Its Art Deco architecture and interiors attracted international royals, celebrities, and political figures, with a guest book that includes names such as Nikola Tesla, Winston Churchill, Zsa Zsa Gabor, and the Obamas. Following an extensive multi-year closure for comprehensive renovations, the landmark property planned its grand reopening. Rates begin from $1,221 per night, offering guests access to a spa, fitness center, concierge services, and room service.
The Balmoral Hotel in Edinburgh
A prominent landmark in the Scottish capital, the Balmoral is widely recognized for its 190-foot clock tower—which has been famously set three minutes fast since the hotel opened in the early 1900s, with the sole exception of New Year’s Eve. Author J.K. Rowling famously finished the final Harry Potter book in Suite 552 on January 11, 2007, an event commemorated by an owl door knocker and an in-room bust of the Greek god Hermes signed by Rowling.
The hotel’s sprawling bedrooms offer cozy design elements, including contemporary wallpaper prints, neutral plaid furniture, and wool bed covers, with several rooms framing picturesque views of Edinburgh Castle. Stays start from $399 per night, featuring amenities such as a spa, an indoor lap pool, three on-site restaurants, whisky-tasting experiences, and traditional afternoon tea.
The Carlyle Rosewood Hotel in New York
Nestled on 76th Street just off Madison Avenue, the Carlyle first opened its doors in 1930. In the decades since, presidents, royalty, and prominent film stars have frequented the hotel. The interiors blend Art Deco touches and New York eclecticism with classic architecture through a layered mix of vintage-inspired furniture silhouettes, contemporary art, and crystal chandeliers.
One of the property’s main attractions remains the iconic Bemelmans Bar, which is outfitted with whimsical wall murals painted by Madeline author and illustrator Ludwig Bemelmans. Alongside classic cocktails, the bar serves signature drinks paying homage to longtime Café Carlyle cabaret fixture Bobby Short. Rates begin from $1,323 per night, offering presidential and celebrity clientele proximity to Central Park.
Hotel Figueroa in Downtown Los Angeles
Marking its centenary, Hotel Figueroa originally opened its doors as a safe haven for solo female travelers, financed, owned, and operated by the Young Women’s Christian Association (YWCA). Uniquely for its era, the property permitted unaccompanied women to check in without a male chaperone, a practice prohibited by most hotels at the time.
Today, the property embraces Spanish Revival design influences, featuring curated art exclusively by female artists, sophisticated tilework, and modern furnishings. Guests can utilize the coffin-shaped pool dating back to the 1920s while surrounded by decades-old cacti, enjoying craft cocktails from the poolside bar or dining at the on-site restaurant. Stays start from $129 per night, with pet-friendly accommodations and midcentury pool access included.
Brown’s Rocco Forte Hotel in London
Widely recognized as London’s oldest luxury hotel, Brown’s has incorporated updates like glossy marble bathrooms, vibrant textiles, and mahogany walk-in closets while maintaining homages to its original architecture through stained-glass windows, untouched entryways, and wrought-iron façade detailing.
The property has hosted notable literary figures throughout its history, including Rudyard Kipling, Bram Stoker, Agatha Christie, and Stephen King, the latter of whom outlined his bestselling novel Misery during a stay. Situated in the upscale Mayfair neighborhood near Buckingham Palace and Hyde Park, the hotel offers proximity to world-class shopping and museums. Rates begin from $966 per night, featuring traditional afternoon tea, live music, and personalized guest experiences.