Why limit yourself to just one destination when you could spend your vacation driving along Route 66? This famous highway—turning 100 this year—passes through lively cities, natural sights, and quirky roadside attractions, so there’s plenty to see and do along the way.
Since Route 66 stretches 2,448 miles across much of the United States, you’ll want to plan a few rest stops. While the main road has some boutique hotels and classic motels, booking an Airbnb can give you a home away from home during your trip. That’s especially nice if you want to extend your breaks, add in some sightseeing, and get some rest and relaxation.
Vogue’s Best Airbnbs Near Route 66
Best for Families: Boutique Historical Home in Edmond, Oklahoma, from $295 per night
Best for Digital Nomads: Classic Logan Square Bungalow in Chicago, Illinois, from $316 per night
Best for Going off the Grid: Casa de la Cruz in El Rito, New Mexico, from $520 per night
Best for Large Groups: Evergreen House in Flagstaff, Arizona, from $438 per night
Best for Design Aficionados: Modern Tree House in Topanga, California, from $1,305 per night
To pick these stays, being close to the main road was the top priority. But just because practicality comes first doesn’t mean style is ignored—you’ll find plenty of wood-beamed cabins ahead. Here are 10 Route 66 Airbnbs that make great stops along the Mother Road.
Classic Logan Square Bungalow
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If you’re mixing your road trip with some remote work, choose a place set up for digital nomads. This bohemian bungalow in the heart of Chicago’s Logan Square neighborhood has both a private office and high-speed internet. It’s a stylish spot to tick off a few tasks before you hit the road again.
Rooms: 2 bedrooms, 1.5 bathrooms
Amenities: High-speed internet, private home office, bathtub, washer/dryer
Location: Chicago, Illinois
Best For: Remote workers.
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Architect-Designed Oak Park Flat
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Want to start your road trip with a design-forward vibe? Check into this flat in Chicago’s historic Oak Park neighborhood. Although this two-bedroom apartment dates back to the 1920s, local firm Elements Architectural Group lovingly restored it in 2023. The result is sleek, polished, and effortlessly cool: an all-wood galley kitchen, modern lighting, and an emerald-tiled shower are our favorites. Bonus: It’s near the Chicago L’s green line, so you can explore the Windy City on foot.
Rooms: 2 bedrooms, 1 bathroom
Amenities: Shared balcony, crib, washer/dryer, free parking
Location: Chicago, Illinois
Best For: Design-minded travelers.
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The Pied-à-Terre & Garden
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Located in a building from 1908, this spacious 1,500-square-foot unit sits near the city’s best shops, restaurants, and bars. You could head out for a post-drive date night, or enjoy a glass of wine in the unit’s lush courtyard. There’s a grill and outdoor kitchen there, so you can whip up a quick dinner before getting back on the road the next day.
Rooms: 2 bedrooms, 1 bathroom
Amenities: Private garden, dedicated workspace
Location: St. Louis, Missouri
Best For: Couples wanting a cozy rest stop.
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Charming Carriage House
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City and country come together at this Oklahoma City carriage house, which sleeps up to four guests. Whimsical touches like a built-in bed, wallpaper accents, and cutout details along the stairwell give it the feel of a quaint cottage off the beaten path. But in reality, it’s right in the heart of the city, with easy access to restaurants, museums, and the popular Bricktown entertainment district.
Rooms: 2 bedrooms, 1 bathroom
Amenities: Pet-friendly, crib and toys, dedicated workspace, washer/dryer, free parking
Location: Oklahoma City, Oklahoma
Best For: A charming cottage with city convenience.
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Boutique HistoricaHome
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From the occasional motion sickness to the constant “are we there yet?” questions, road-tripping with kids is no easy task. If you’re bringing them along, you’ll want a comfortable place to stay with enough room for everyone to get some alone time. Tucked away in Clegern Place—a historic neighborhood in Edmond, Oklahoma—this 1950s mid-century gem has been updated with families in mind. The single-story layout is great for little ones who are crawling, and the home comes with cribs, high chairs, and toys, so you can leave some extra space in your trunk.
Rooms: 3 bedrooms, 2 bathrooms
Amenities: Barbecue, outdoor furniture, crib and high chair, and a dedicated workspace.
Location: Edmond, Oklahoma
Best For: A family-friendly stay.
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Casa de la Cruz
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This three-bedroom adobe is about an hour from Santa Fe—a key stop on Route 66—but it’s worth the extra drive. Casa de la Cruz sits on a 12-acre property next to Carson National Forest, and it’s just a 10-minute drive from Georgia O’Keeffe’s home in Abiquiú. While art lovers and thrill-seekers will enjoy the detour, everyone will appreciate the peaceful setting at the end of the day. Cozy up by the wood-burning fireplace in the living room, or head outside for some late-night stargazing.
Rooms: 3 bedrooms, 3 bathrooms
Amenities: Firepit, outdoor grill, wood-burning fireplace, and mountain views.
Location: El Rito, New Mexico
Best For: Art lovers hoping to follow in Georgia O’Keeffe’s footsteps.
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Sky-High Desert Oasis
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If you’re looking for an Airbnb with a view, it doesn’t get much better than the Sky-High Desert Oasis in Albuquerque, New Mexico. Designed by architect Bart Prince, this sculptural space features floor-to-ceiling windows and six viewing decks with stunning views of the Sandia Mountains. For guests who want to get even closer to nature, there’s a private hiking trail that connects to Sandia Peak.
Rooms: 3 bedrooms, 2.5 bathrooms
Amenities: Home gym, private hiking trail, dedicated workspace, crib, and toys.
Location: Albuquerque, New Mexico
Best For: Architecture enthusiasts.
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Evergreen House
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Road-tripping with a big group? Book a stay at the Evergreen House, a dog-friendly rental in Flagstaff that sleeps up to eight guests. Set on five acres of land, this remote home has plenty of space for everyone—humans and pets alike—to stretch their legs after a long drive. The Airbnb also comes with a hot tub, a nine-hole disc golf course, and lots of board games, so there’s always something to do.
Rooms: 3 bedrooms, 2.5 bathrooms
Amenities: Hot tub, nine-hole disc golf course, bathtub, washer/dryer, pet-friendly, indoor fireplace.
Location: Flagstaff, Arizona
Best For: Large groups (and those with pets).
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Dreamland 1920’s Hunting Cabin
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Think of this 1920s bungalow as the perfect mix of old Hollywood charm and modern comfort. Nestled in the Hollywood Hills, this compact cabin is surrounded by lush greenery, offering a quiet escape from the city. (There’s even a small bedroom with skylights so you can feel close to nature.) And when you’re ready for a taste of star-studded Los Angeles, the Sunset Strip is just down the hill.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Private patio, dedicated workspace, washer/dryer, bathtub, and outdoor dining area.
Location: West Hollywood, California
Best For: A blend of seclusion and star power.
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Modern Tree House
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Once you reach the end of Route 66 in California, unwind in this modern treehouse in Topanga, a laid-back neighborhood in the Santa Monica mountains. Vaulted ceilings, oversized windows, and a very mid-century modern living area create a calm backdrop that’s especially welcome after a long drive. You could drive 10 minutes to the nearby beach, but the properThe hot tub, gym, and spacious balcony provide a spa-like atmosphere right where you’re staying. In the evening, pull down the projector screen for a cozy movie night.
Rooms: 3 bedrooms, 3.5 bathrooms
Amenities: Hot tub, private gym, movie projector, and ping pong table
Location: Topanga, California
Best For: Tired drivers looking for a relaxing getaway at the end of the road.
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Frequently Asked Questions
Here is a list of frequently asked questions about the 10 best Route 66 Airbnbs designed to help travelers plan their trip
General Questions
1 What makes an Airbnb a Route 66 Airbnb
It usually means the property is located directly on the historic highway is housed in a restored vintage motel or gas station or is decorated with heavy neon retro and Americana themes to match the road trip vibe
2 Are these Airbnbs actually on the original Route 66 or just near it
It depends on the listing Some are literally on the original pavement while others are a short detour off the modern interstate in towns that the old route passes through Always check the map and the listing description to see exactly where they sit
3 Do these places have typical hotel amenities like daily housekeeping
No These are homes or private suites not hotels You wont get daily towel changes or room cleaning However they usually come with full kitchens laundry facilities and more spaceyou just have to handle the tidying yourself
4 Is it cheaper to stay in a themed Airbnb or a chain motel on Route 66
Chain motels are often cheaper and more predictable Youre paying a premium for the nostalgia unique decor and the experience of sleeping in a piece of history If you just need a bed go with a motel if you want a memory go with the Airbnb
Booking Planning
5 How far in advance should I book these popular Route 66 Airbnbs
As soon as you know your datesideally 3 to 6 months in advance The famous ones book out solidly during peak season and for major events like the Route 66 Mother Road Festival
6 Are these properties suitable for families with kids
Most are but you need to read the listing carefully Some vintage properties have staircases slanted ceilings or antique furniture that isnt childproof Look for listings that specifically mention familyfriendly or packnplay available
7 Can I book just one night or is there a minimum stay
Many of the best and most unique properties have a 2night minimum stay especially on weekends However