Of all the road trips a traveler can make in the United States, none is more epic than Route 66. The 2,448-mile Mother Road has been memorialized in music, film, and literature for nearly a century, with everyone from John Steinbeck to John Mayer finding inspiration in its lonesome stretches of nothingness punctuated by small towns and cities. The historic highway, which started in Chicago and ended in Santa Monica, served as one of the original thoroughfares in the US highway system. Its popularity exploded in the 1930s and ’40s, with Depression–era migrants using it to decamp from the Dust Bowl to the Pacific coast.
The route was decommissioned in 1985, but many of its original sections have been preserved. The drive today can be done in a week or less, but it’s better to go slow and savor the journey. While it’s fun to book a night at one of its famously kitschy motels (Wigwam Motel in Holbrook, Arizona and Munger Moss Motel in Lebanon, Missouri spring to mind), there are scores of Airbnbs to check out as well—especially if you want a kitchen or laundry. The dozen-plus properties that follow are all located close to the original route—and some are even decorated with Mother Road memorabilia. Each one is run by a Superhost with a rating of 4.8 or above, too, so you know you’re in good hands. Below, the best Airbnbs on Route 66.
All listings featured in this story are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.
An airy-bright studio in Chicago, Illinois
Bed & bath: Studio, 1 bath
Nearby attractions on Route 66: The long-defunct Castle Car Wash at the corner of Ogden and Hamlin was built in 1925 and rumored to be a hideout for Al Capone.
If you’re going for the full Route 66 experience, start in Chicago at this crisp, clean studio in Humboldt Park. Housed in a converted 1930s machine shop, the midcentury-inspired rental has 14-foot-tall tin ceilings with original steel I-beams and loads of thoughtful touches such as a luggage rack, full-length mirror, yoga mats, local travel guides, and houseplants at every turn. The clawfoot bathtub is visible from the living room, so the layout is best suited to solo travelers, couples, or very good friends. There is a kitchenette with Dansk cookware, too, but given the free street parking and walkability to great restaurants, you might not need it.
A charming ranch in Rolla, Missouri
Bed & bath: 3 bedrooms, 1.5 baths
Nearby attractions on Route 66: The tchotchkes-packed Totem Pole Trading Post has roots dating to 1933, making it the longest-running business on the Missouri leg.
Six hours from Chicago, this south central town of 20,000 is a natural stopping point on Route 66—and, fortunately, it has a plethora of rental options. This recently renovated ranch house sits on a bucolic half-acre in a quiet neighborhood. The zen of the outdoors continues inside with a calming color palette and handsome furnishings including woven leather ottomans, globular pendant lamps, and a vintage wicker headboard in one of the bedrooms. Among its other charms: a private backyard, garage, and washer and dryer.
A boho-modern cabin in Rolla, Missouri
Bed & bath: 2 bedrooms, 1 bath
Nearby attractions on Route 66: The mini-Stonehenge monument .4 miles from the route was carved in 1984 to demonstrate the capabilities of Missouri S&T’s High Pressure Waterjet Laboratory.
This striking black cabin with butter yellow shutters deserves to live on a Pinterest board. Nestled on a 40-acre wooded lot near a scenic creek, the unit has a private bedroom and bath on the ground floor plus a second bedroom in the upstairs loft. There’s a small convertible sofa bed better suited to children than adults, but the cabin’s steep, open staircase dating back to the 1800s would make this rental challenging for families with babies or toddlers. Outdoor amenities include a partly shaded deck, charcoal barbecue grill, hammock, fire pit encircled by tree-stump seating, and easy access to nearby trails. The record player, board games, and HDTV hookup with Apple, Disney+, Hulu, and Netflix keep travelers entertained after dark.
A retro pad in Riverton, Kansas
Bed & bath: 2 bedrooms, 1 bath
Nearby attractions on Route 66: Cars on the route inhabits a restored 1934 Kan-O-Tex gas station in Galena, about five minutes east of Riverton, and displays an array of anthropomorphic vehicles inspired by the animated Pixar movie Cars.
The Kansas leg of Route 66 is the shortest in its eight-state run (just 13 miles!), but this playfully decorated rental goes all out embracing the nostalgia. The historic building is located two blocks from the Mother Road and channels days of yore with its whimsical vintage furniture (love that chrome-and-formica dinette), checkerboard kitchen floor, framed photos of Elvis Presley, and art pieces fashioned from rusty license plates. The second-story apartment has a private covered balcony and two separate bedrooms, as well as a sofa bed, air mattress, crib, and baby gates; it’s also pet-friendly.
A historic retreat in Oklahoma City, Oklahoma
Bed & bath: 2 bedrooms, 2 baths
Nearby attractions on Route 66: The Pops 66 Soda Ranch in Arcadia is a restaurant, gas station, and convenience store with international sodas and a 66-foot-tall bottle as its beacon.
Details matter in this lovingly restored and updated 1940s Tudor home roughly 3.5 hours from Riverton. From the Art Deco-style velvet chairs and mantle in the living room to the sleek black-and-white kitchen with honeycomb tile, the property looks straight out of a design magazine. Guests rave about its convenient location, with easy highway access and close proximity to restaurants and shops. There is off-street parking, a swing on the covered veranda, and a big fenced backyard—music to the ears of road trippers with pets in tow. Other perks include a well-equipped kitchen, washer and dryer, and 65-inch HDTV for screening Easy Rider.
A roadside attraction-packed house in Tulsa, Oklahoma
Bed & bath: 3 bedrooms, 1.5 baths
Nearby attractions on Route 66: The cartoonish Blue Whale of Catoosa is a super-sized marine mammal sculpture leftover from a private zoo.
If you want to travel a bit slower, consider a stay in Tulsa, only two hours south of Riverton. There you’ll find the incredible Buck’s Cosmic Crash Pad tucked behind Route 66 mainstay Buck Atom’s Cosmic Curious souvenir shop. The rental lives up to its reputation as a kooky “living gallery” packed with retro art, most of which is for sale. Three bedrooms sleep up to six guests, making it a fantastic option for families. Kids will flip out when they spot the larger-than-life robot lording over the fenced-in backyard.) Glowing neon signs, vintage record cabinets, and kitschy beaded curtains aside, there are modern touches where it matters most—to wit, the good-quality linens and spotless, subway-tiled kitchen with gleaming stainless steel appliances.
Courtesy Airbnb
A ‘Mad Men’ homage in Norman, Oklahoma
Bed & bath: 3 bedrooms, 2 baths
Nearby attractions on Route 66: The National Weather Center at the University of Oklahoma goes deep on climate science via its interactive weather exhibits.
This beautifully maintained property from the 1960s was the handiwork of a fine art furniture builder and University of Oklahoma faculty member. Hand-crafted solid wood cabinetry can be found throughout, along with vintage furnishings and authentic mid-century light fixtures. The living room has a wood-burning fireplace and game table; the galley kitchen has a Don Draper-esque dry bar. The home is nestled on a wooded lot, making the view from its floor-to-ceiling windows even more serene, and the outdoor draws include a hot tub, fire pit, gas grill, and loaner bicycles.
A time capsule in Amarillo, Texas
Bed & bath: 3 bedrooms, 1 bath
Nearby attractions on Route 66: One of the route’s best-known art installations, Cadillac Ranch, features 10 vintage cars buried nose-down and caked in graffiti. (BYO spray paint.)
You’d never guess what the inside of this modest brick house in the Texas Panhandle looks like, though the cherry-red clamshell chairs on the porch hint of the time travel to come. Every space in this three-bedroom home channels a different decade, from a kitschy Wonder Years-era living room to a radically awesome ’80s-themed bedroom, complete with taffeta prom dresses hanging in the closet. But the best room has to be the Grease-is-the-word kitchen, complete with a 1950s checkerboard floor, robin’s egg blue cupboards, and chromed-out dinette set. Vintage games like Twister complete the back-to-the-future wormhole experience.
A desert casita in Los Cerrillos, New Mexico
Bed & bath: 1 bedroom, 1 bath
Nearby attractions on Route 66: It’s not everyday that you get to order a burrito in a saloon built in 1885, but that’s exactly what awaits you at the historic Black Bird Saloon in Los Cerrillos.
Once upon a time, the mines in Los Cerrillos were rich in gold, silver, lead, zinc, and turquoise. Today, the ye olde Wild West town looks like a movie set with its dirt roads—and, in fact, it was: Young Guns was filmed here in 1988. But the real reason to stay near Los Cerrillos is this 10-acre swathe of land with vistas of painterly rock formations and the breathtaking Ortiz Mountains. The hiking, biking, and stargazing are phenomenal and the house itself is a stunner: all glass block windows, Otomi textiles, and ristras hung from the welcome sign. The kitchen is on the smaller side but still has everything you need for a comfortable stay, plus a wood-fed stove to make holing up extra hygge in winter.
A cheerful cottage in Santa Fe, New Mexico
Bed & bath: Studio, 1 bath
Nearby attractions on Route 66: The Turquoise Trail, the scenic byway that links Santa Fe to Albuquerque, follows the path of the original Route 66 and is dotted with historic mining towns, quirky museums, trading posts, and saloons.
This freestanding guest house with gated off-street parking is five to 10 minutes from most points of interest in Santa Fe yet far enough removed from downtown that you won’t hear traffic. Its standout features include a bubblegum-pink Smeg fridge, antique chandeliers, exposed wood-beam ceiling, spacious tiled shower, and a private garden patio with a fringed Anthropologie-esque sunbrella and views of the sweeping Sangre de Cristo Mountains.
A rambling hacienda in Santa Fe, New Mexico
Bed & bath: 3 bedrooms, 3 baths
Nearby attractions on Route 66: Pay a visit to the Georgia O’Keeffe Museum in Santa Fe to learn how the surrounding environs inspired her artwork.
If gallery-packed Canyon Road is the heart of Santa Fe, this arty home may be its soul. Once the neighborhood shop, complete with burro parking, the luxurious property now sports a light-flooded living room and freshly renovated kitchen, both with exposed wood beams, and a trio of striking kiva fireplaces. Handmade touches abound, from the woven textiles and delicate ceramics to the colorful paintings that pop off the walls. The private back patio has an electric barbecue and a gate that leads to two off-street parking spots, though you may not need them; the rental is walkable to Santa Fe’s historic Plaza and other sights of note.
A big-drama tiny house in Williams, Arizona
Bed & bath: 1 bedroom, 1 bath
Nearby attractions on Route 66: Pete’s Route 66 Gas Station Museum is a restored service station packed with Mother Road keepsakes and souvenirs.
Six hours further west, and just 60 miles south of the Grand Canyon, this town of roughly 3,200 residents is a smart stopping point before crossing into California. This 350-square-foot tiny house with the dramatic vaulted ceiling incorporates reclaimed wood from an original 1920s carriage house, but is now gussied up with luxe amenities such as an extra-deep Kohler soaking tub. The loft is accessible via a rolling library ladder and features a queen-size memory foam mattress; if you need extra bedding, there is a leather futon downstairs with a pillow topper and sheets. The kitchenette has a full-sized refrigerator, microwave, hot plates, and a convection oven, and a high chair and travel crib are available for families. The property has more than one Airbnb rental, so some amenities (barbecue grill, fire pit, corn hole court) are shared.
An MCM loft in Santa Monica, California
Bed & bath: 1 bedroom, 1 bath
Nearby attractions on Route 66: The iconic Route 66 End of the Trail sign at the edge of the Santa Monica Pier marks the official terminus of the Mother Road.
Route 66 ends where the ocean begins, so it’s only fitting that you wrap things up in Santa Monica. Superhost Kevin provides a space for overnight parking, but this newly remodeled studio is also an easy stroll to both the beach and 3rd Street Promenade. The loft is painted bright white and blessed with abundant natural light; a spiral staircase, drum kit, punchy orange sofa with shag pillows, and vintage cameras bring the personality. Guests also rave about the snack-packed welcome basket and sunny private balcony.