As Historic Route 66 celebrates its centennial in 2026 (November 11 is the date to circle on your calendar), the time is ripe to hit the Mother Road. Throughout the year, cities and towns between Chicago, Illinois, and Santa Monica, California, will host special events commemorating the legacy of the highway. Here are some of the best Airbnbs in historic towns along US Route 66, close to roadside attractions and old-school diners.
We hope you love these Route 66 Airbnbs! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Family-friendly Airbnb with a hot tub — Pontiac, Illinois
With 24 outdoor murals celebrating car culture and classic brands (and not forgetting the Route 66 Hall of Fame) a stay in Pontiac, Illinois, sets you up nicely for the ultimate US road trip. This three-bedroom vacation rental has a modern kitchen, laundry facilities, and a private hot tub in the backyard where you can decompress after a long drive — or toast the start of your ride west.
Not to be confused with the island, Cuba, Missouri, is another Historic Route 66 outpost where the streets serve as an open-air gallery. Stick around for the night so you have time to have a gander at the murals, take selfies with the “World’s Largest Rocking Chair,” and dine at one of downtown’s epic diners. This cabin stands in the woods on the outskirts of town, close to wineries and hiking trails.
Considered the Capital of Route 66, Tulsa, Oklahoma, is heaving with kooky roadside attractions, retro diners, and neon signs aplenty. This romantic Airbnb in downtown Tulsa has a fully-equipped kitchen, a treetop deck, and a private hot tub in the backyard. It’s peaceful by night but close enough to walk to coffee shops and drive to sights like the Blue Dome and the Mother Road Market.
Twenty minutes from Oklahoma City, this El Reno Airbnb sits right off Historic Route 66 and Interstate 40. Decorated with a vintage flair, the house has some surprising features — a room dedicated to The Beatles being one of them. There’s ample seating on both porches with a hot tub on the rear deck. Besides checking out the old trolley and preserved gas stations, be sure to grab a fried onion burger from one of El Reno’s diners.
Known for Cadillac Ranch and its 72-oz steak challenge, Amarillo is also a base for exploring the wild side of Texas — pad out your road trip with a day in Palo Duro Canyon State Park. This 1920s bungalow sits on the edge of the Amarillo Route 66 Historic District, close to boutiques and breweries, and minutes from a splash pad. The fenced backyard has a lawn for the kids to run around and a fire pit.
Tucumcari, NM, is home to one of the most famous motels on Historic Route 66. But, if you can’t get a room at the Blue Swallow, this micro-castle Airbnb ought to do the trick. This hacienda-style residence has adobe walls and quintessentially southwestern accents. The rental has a private backyard where you can soak up the rays with a cold beer after a long drive.
This colorful tiny home has a loft bedroom, a full kitchen, and a modern bathroom. The backyard is a haven, with a private hot tub and grill with some photographic backdrops. Although technically a neighborhood, Barelas retains a sense of independence from Albuquerque, NM, and is considered one of the oldest parts of town. You’ll be able to explore the museums and restaurants of downtown, Old Town, and Nob Hill easily from here.
Made famous by the Eagles in their song, Take It Easy, Winslow, AZ, is also a hub for learning about railroad heritage and Native American culture during a Route 66 road trip. This restored church Airbnb is a short walk from the Standin’ on The Corner Foundation and local history museums. Packed with antiques, it has one bedroom and a clutch of vintage couches for additional sleepers.
The small town of Seligman, AZ, is where preservation efforts for Route 66 began in the 1980s. Visited in tandem with Kingman, AZ, these twin towns feel like a living museum. This comfortable three-bedroom rental has ample parking for campervans and motorbikes with a front yard overlooking the neon-clad highway. Start your evening here before joining town denizens at the boozer next door.
Eight guests, three bedrooms Price: $214 per night
Arriving in the Golden State, you can choose between a teepee at the iconic Wigwam Hotel or this US Route 66-themed shipping container in San Bernardino, CA. This unique one-bedroom rental touts Mother Road memorabilia and a playful lighting system. It’s fairly rural — the closest stores are a 20-minute drive — so you’ll want to stock up on groceries before arrival.
Finish your road trip the right way, by catching the sunset at Santa Monica Pier and dipping a toe in the Pacific Ocean. This Guest Favorite Airbnb in Santa Monica, CA, has one bedroom, a full kitchen, and a designated parking space. The garden is perfect for breakfasts and enjoying an evening glass of wine while planning your next road trip.
