12 Best Historic Hotels and Airbnbs That Feel Like Time Traveling (2026)

There are plenty of impressive stays out there, no matter your destination of choice. But booking a historic hotel or Airbnb rental with a storied past—tales of tenants, centuries-old architecture, or whatever else might land a property on a local registrar—is the difference between a simple spot to snooze at night and your next dinner party conversation. From former artists’ homes and firehouses to castles and celebrity-studded hotels, we’ve curated several beguiling places around the world to lay your head at night. As is the case with older buildings, some require a bit of flexibility—say, an outdoor shower or a less-than-fully-equipped kitchen—while others offer a portal to the past (some spots on this list predate the 16th century) rich with amenities and luxury.

The following historical hotels and homes have a story to tell, and guests get a front-row seat.

Still Bend Schwartz House in Wisconsin

Perks: Shared beach access, in-unit washer and dryer, sound system, indoor fireplace, fire pit

Architect Frank Lloyd Wright built a lot of incredible spaces for others, but this is the very one he contributed to a Life Magazine article back in 1938 as part of a feature about dream homes. The four-bedroom estate is full of windows (the 63-foot living room has an entire wall of them), and each space is bursting with midcentury furniture and decor. Walking into each room feels like unlocking 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 Wisconsin, the fire pit (and hammock) outside is still inviting come winter and snow. From $841 per night.

The Scriptorium in Glasgow

Perks: Badminton net, steam room, gym, BBQ grill, EV charger

This is the perfect pit stop on a road trip through the Highlands. Hidden in the depths of a former abbey, this one-bedroom space used to be the “writing room” for the monastery. The bed is surrounded by stained glass windows, which look out over the gardens and Loch Ness (yes, of Nessie fame). Guests have access to the neighboring Highland Club, which houses an incredible indoor pool, sauna, tennis court, and so much more. While the kitchen and appliances are newer additions, you will find pieces of furniture from the original space peppered throughout the rental (a wooden bench here, a tapestry there). From $468 per night.

Anemomilos in Greece

Perks: Pet friendly, patio, free parking, pool, outdoor shower

If daydreams of your next trip are filled with al fresco dinners, this two-bedroom home will do you one better by adding bird’s-eye ocean vistas to the scene. Once a windmill that used to grind wheat for flour production, it now houses an outdoor kitchen, a bedroom with a view, and an outdoor shower. The scenes from the top bedroom are really something to write home about—wake up to mountain views and the ocean beyond. The pool is the best spot to take in the sunset before retreating to the open-air dining space for good eats and conversation. From $224 per night.

Macchiaroli Castle Teggiano in Italy

Perks: Pet friendly, Wi-Fi, luggage drop-off, radiant heating, fireplace

This historic Airbnb is known as La Romantica, which should tell you all you need to know. The one-bedroom rental can be found in the oldest section of the property (which dates back earlier than the 1400s), there’s a private entrance, ancient stone walls, antique Italian furniture, and a fireplace that’s perfect for fighting off a chilly night. This is a spot where you do a bit of time traveling, both indoors and out when you decide to explore the surrounding UNESCO heritage town, Teggiano, which is known for its museums (the Diocesan Museum, Herb Museum, and Museum of Folk Traditions, to name a few) and its 13 churches. Guests at this one-bedroom stay are located right in the middle of town and within walking distance of everything you’d need, so slipping out for a quick dinner, coffee at one of the cafes, or a sunset stroll along medieval architecture is always on the itinerary. From $154 per night.

Historic Firehouse 4 in Washington, DC

Perks: Pet friendly, air conditioning, private parking available, fireplace, historic decor

Built in 1884, this was Washington, DC’s first fully African American fire company and the set of a Netflix show: Check out Stay Here, season one, episode eight. Located in the Shaw neighborhood, a historic district, there are plays to attend (Howard Theatre), drinks to be had (Blagden Alley), and music to take in (Eighth Street Lounge and Bar). The five-bedroom rental even has the original fire pole and you can see previous tenants in the photography that decorates the walls. From $860 per night.

The Pond House in New York

Perks: Shared beach access, sound system, exercise equipment, fire pit

Step right into the world of painter Reginald Marsh when you stay at this two-bedroom getaway with forest views. A pond anchors one side of the property, and the expansive lawns are landscaped with long, post-dinner strolls in mind. As secluded as it feels, it’s a short walk to the center of Woodstock and all of its restaurants, bars, cafes, and shops. And while you’re not near any national parks, the home’s private waterfall (you read that correctly) borders a public preserve that’s open for exploring. The library inside will pull you back indoors, though, as will the wood-burning stove on chilly nights. The outdoor dining space is great for summertime grilling, but the full kitchen indoors is a delight to work in. From $619 per night.

The Luxury Palace Hotel in Madrid

Perks: Central location, trendy bars and restaurant, 24-hour fitness center, balcony access, Aqua di Parma and Byredo toiletries

Centrally located in Madrid’s Plaza de las Cortes, the historic Palace Hotel reopened its doors in 2025 to unveil property-wide updates—including its main lobby, dining accommodations, and 470 rooms—the result of a two-year renovation project with reimagined interiors by designer Lázaro Rosa-Violán. Dating back to 1912, The Palace has seen notable guests like Salvador Dalí and Ernest Hemingway, and is even credited as the first hotel in the country to have private toilets in its quarters.

Today, guests can appreciate pieces of the property’s historic past through a modern lens. Surrounded by bespoke fixtures custom designed by Rosa-Violán, vintage tapestries hang with contemporary Joan Miro prints in La Cúpula Restaurant. Inside the inviting suites, updated bathrooms feature original red marble stone reminiscent of Paloma Elsesser’s luxurious tub. 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 stroll through El Retiro Park. “The hotel staff at The Palace are some of the friendliest I’ve encountered,” says 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.” From $1,060 per night.

The Waldorf Astoria in New York

Perks: Spa, fitness center, concierge, Smart TVs, room service

The history of the Waldorf Astoria runs deep. Originally designed in 1893 as two side-by-side hotels built by feuding family members, the collective property was demolished in 1929 to make room for the Empire State Building’s construction. It was reopened in its current Park Avenue location in 1931, breaking records as the largest and tallest hotel in the world (at the time). Its Art Deco architecture and interiors caught the eyes of royals, celebrities, and politicians around the world. The guest book includes names such as Nikola Tesla, Winston Churchill, Zsa Zsa Gabor, the Obamas, and so many more. After being closed for extensive renovations, the property is planning a grand re-opening for Spring 2025. From $1,221 per night.

The Balmoral Hotel in Edinburgh

Perks: Irene Forte spa, indoor lap pool, three on-site restaurants, whisky tasting experience, afternoon tea, views of Edinburgh landmarks

A historic landmark, the Balmoral is widely recognized for its 190-foot clock tower—famously set three minutes fast, except on New Year’s Eve—that has been part of the Edinburgh skyline since opening in the early 1900s. J.K. Rowling even finished the final Harry Potter book on January 11, 2007, in Suite 552—now commemorated with an owl door knocker and an in-room bust of the Greek god Hermes that Rowling signed. “The Balmoral does rest and relaxation like no other through comforting amenities, charming interiors, and hearty cuisine,” says 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 also return for the sprawling bedrooms, some of which frame picturesque views of Edinburgh Castle. The stays showcase cozy design with contemporary wallpaper prints, surprisingly neutral plaid furniture, and ultrasoft wool bed covers. From $399 per night.

The Carlyle Rosewood Hotel in New York

Perks: Presidential, royal, and celebrity clientele; iconic Bemelmans Bar; walking distance to Central Park

Nestled on 76th Street off Madison Avenue, the Carlyle first opened its doors in 1930. Since then, presidents, royalty, and movie stars have all sought refuge in the hallowed hotel. “You can have breakfast next to Daniel Patrick Moynihan or Tom Ford,” Los Angeles–based designer and AD100 Hall of Famer Michael S. Smith once described. “It's like a big hotel in a small town, the grande dame of New York.” 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 splashy chandeliers. One of the hotel’s top attractions for locals and hotel guests alike is the iconic Bemelmans Bar, outfitted with whimsical wall murals by Madeline author and illustrator Ludwig Bemelmans. The classic martini is a failsafe order, though you could go for the namesake Madeline's Vesper or Bobby’s Manhattan (an homage to cabaret singer Bobby Short, a longtime fixture of Café Carlyle, another classic destination within the Carlyle). From $1,323 per night.

Hotel Figueroa in Downtown Los Angeles

Perks: Midcentury pool, pet-friendly

This year, Hotel Figueroa celebrates its 100th birthday. The Young Women's Christian Association (YWCA) originally financed, owned, and operated the Downtown Los Angeles fixture to function as a safe haven for solo female travelers. The property allowed unaccompanied women to check in without a male chaperone—something most hotels prohibited at the time. Today, Spanish Revival design influences flourish in the space: Expect curated art (exclusively by female artists), sophisticated tilework, and modern furnishings. As you dip in the coffin-shaped pool straight from the 1920s while surrounded by 50-year-old cacti, enjoy craft cocktails and bites from the poolside bar, La Casita. For a more substantial meal, the restaurant-in-residence Florence by the Water serves up Italian classics. From $129 per night.

Brown's Rocco Forte Hotel in London

Perks: Proximity to landmarks, celebrity guest roster, traditional afternoon tea, live music, private tours and experiences available upon request

Widely recognized as London’s oldest luxury hotel, updates like glossy marble bathrooms, vibrant textiles, and mahogany walk-in closets have breathed new life into the historic stay. At the same time, homages to the original architecture—in stained-glass windows, untouched entryways, and wrought-iron façade detailing—forge bonds to its 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,” says Lee. Past literary guests of note include Rudyard Kipling, Bram Stoker, Agatha Christie, and Stephen King; King even outlined his bestseller Misery during one of his stays. Situated in the upscale Mayfair neighborhood, world-class shopping and top London museums ensure your agenda stays full. From $966 per night.

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