There are plenty of impressive stays out there, no matter your destination of choice. But booking a historical 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.
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 $720 per night.
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 $417 per night.
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 $660 per night.
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 $162 per night.
Perks: Air conditioning, washer and dryer, luggage drop-off, board games, TV
Due to the meticulous preservation of the frescoes in this Airbnb, it doesn’t feel entirely unlike stepping into an oil painting the moment you open the door. The neighborhood’s architecture reflects late-19th-century Istanbul, so guests are surrounded by historic charm before they even walk inside. The fourth-floor apartment has views over the Bosphorus, as well as Galata Tower and the Golden Horn. The original floor plan is intact, but the owners made sure to outfit the three-bedroom home with modern amenities and appliances. Don’t be surprised if the neighbor’s cat wanders in through an open window (the Airbnb host says she's curious). From $300 per night.
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 $1,255 per night.
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 $800 per night.
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.”
Perks: Spa, pool, golf course, hotel-arranged tours and experiences, equestrian school
Just a touch over 100 years old (101, to be exact), this iconic property has always been a hotel welcoming discerning guests. The biggest draw on opening day in June 1992 was its golf course, which helped earn the country hotel the title of “the eighth wonder of the world” by those who first experienced it. Gleneagles closed in 1939 to serve as a military hospital and a miners’ rehab center during World War II, before re-welcoming guests in 1947, though the staff had to follow strict Ministry of Food rationing orders at the time. Flash forward to the present day, and the interiors maintain an old-world charm that’s inspired by the Perthshire countryside. Luxe linens, bed-anchoring slipper chairs, grand common areas—the vibe is timeless. Inside the hotel’s walls, you can also find the country’s only restaurant with two Michelin stars, Restaurant Andrew Fairlie. From $1,580 per night.
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 $1,688 per night.
Craving an escape? From colorful carry-ons to cleverly designed packing cubes (how did we ever travel without them?), shop everything you need to make the journey in style—and as streamlined and stress-free as possible.
