There’s just something about nailing your hotel or private rental stays on an iconic road trip like Route 66.
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Usually, travelers are focused on comfort and location when booking lodging. At hotels, we might look for extra perks like free parking, complimentary breakfast, and something over-the-top, like a rooftop pool. At private rentals, we’re probably after a similar set of amenities—just with more privacy guaranteed.
But that changes when we’re talking about a road trip like Route 66. It’s not just an iconic, cultural journey from Chicago to Santa Monica. It’s a trip for the ages—one that you’ll remember, for better or for worse, for years to come.
A few years ago, I highlighted some of the more stylish motels and inns along the famous route. They might not be the most state-of-the-art, but they’re certainly iconic enough to warrant a stay for a night or two.
Now, I’m going the same with awesome Airbnbs along Route 66 that bring to life that classic Americana feel—just in time for your summer road trip plans. Here are my top selections in major cities along the route, along with smaller towns.
Airbnbs on Route 66 with an Americana feel
Spacious Logan Square Artists Home (Chicago, IL)
This artsy bungalow-style apartment has a slightly Southwestern and eclectic feel. The mid-century pieces and colorful pops of color are giving a slight 70s vibe that feels both classic and playful. Thanks to the hodge-podge of décor and high-design pieces, it’s a fresh take on Americana.
With three bedrooms, this apartment is great if you want to meet up with any friends in Chicago before heading out on your Route 66 adventure! One room is also set up like an office, in case you need to get any last-minute projects turned in. (Or am I projecting?)
Arcade-Chic Bungalow (Saint Louis, MO)
We’ve got another bungalow for your Americana road trip. This unit sleeps four in two bedrooms and has one bathroom. The living room and dining room are set up with more quirky, character-filled décor—which includes two arcade machines and a ping-pong table. Somehow, it melds together into a surprisingly comfortable Airbnb. One that touches on the fun, idiosyncratic spirit of Route 66.
Charming Hummingbird Cottage (Rolla, MO)
From the charming, colorful bungalows listed above, this cottage is a slight departure. The cozy, charming décor will make you feel like you’re staying at Grandma’s house, in the best way possible. There’s even an outdoor patio with a fireplace for cooler nights. Just keep in mind that this is a one-bedroom.
The Route 66 Joplin Hideout (Joplin, MO)
If you breeze past Rolla and want to stay the night in Joplin, Missouri, I’ve got two rentals for you. The first is a one-bedroom that sleeps four. It was setup for Route 66ers, meaning you’ll see some themed décor and have all the amenities you need for a comfortable stay after a long day of driving. It’s not the most Americana-feeling rental, but there is a classic rocking chair in the living room.
If you want to keep with the Americana theme a bit more, you can book a bungalow on Main Street in Joplin instead. It’s a two-bedroom brick home rental. The décor is more modern than a classic Americana setup, but you’ll feel right at home thanks to the familiar design.
Carriage House Standout (Oklahoma City, OK)
This carriage house feels like something from a beloved TV show—warm, lived-in, and comfortable. Though it’s a smaller studio, it’s exactly the type of place that I’d enjoy holing up for a day or two while recovering from long days on the road. Despite its small size, it has a full kitchen and a claw-foot bathtub that’s perfect for a long soak.
Corner ‘Stone’ Cottage (Tulsa, OK)
This cottage looks and feels like an Americana dream, from the exterior’s white siding and American flag to the interior’s homely design and accents. There’s also a backyard where you can play a few yard games or just kick back in the lawn chairs and enjoy a peaceful afternoon.
If you’re looking for a slightly more upscale rental, go with this bungalow instead. The interior is more modern, but still has a classic design. Plus, there are two rocking chairs on the porch—perfect for a little afternoon tea.
Guest Suite with Private Entrance (Albuquerque, NM)
We’ve drifted into Southwestern territory, and you’ll feel it in this guest suite studio rental. The design is very light and airy, almost reminiscent of a beach cottage. However, the Southwestern textiles and the mini-SMEG-style fridge are a callback to the heyday of Route 66. As a perk, this rental also has a massive soaking tub where you can kick back for a spa-like experience.
Beautiful One-Bedroom Casita (Santa Fe, NM)
This gorgeous casita is like a treasure trove of Southwestern design. There are plenty of wooden pieces and features, along with Hopi and Navajo accents. The stone and tiles add a Spanish colonial feel, too. There’s also a small, shaded backyard area where you can get a feel for the land, weather permitting.
Urban Cabin #3 (Flagstaff, AZ)
Bright and full of character, this unit in the Urban Cabin series in downtown Flagstaff is a perfect little setup for you to explore the area while resting up. Some of the features, like the checkered floors, also harken back to the golden era of Route 66. Just know that this rental is built partly of corrugated metal, which I think puts it even more on-theme—it’s kind of like those kitschy motels and inns on the route.
Retro Retreat (San Bernardino, CA)
We’re back where we started—at least, in terms of design. Like the unit in Chicago, this retro retreat-style unit in Highland is a mid-century dream. The décor is fun and austere, while there are funky pieces like the green-velvet poker table. It’s also another three-bedroom, making this last stop a great place to meet up with friends to round off your Route 66 road trip.
