Funky, Cool, And Historic Motels To Help Plan Your Next Coast-To-Coast Roadtrip

The first coast-to-coast highway popped up in the United States back in 1912, and a few years later, a new business began to boom: the motel. Now, people could find affordable lodging without straying too far from their route. Starting on the west coast, motels soon spread across the nation.

With their rising popularity, motel owners started to get creative, giving their lodging an iconic, attention-grabbing look to differentiate it from others. Today, many real estate enthusiasts are sprucing up vintage motels, giving them modern-day amenities while keeping their nostalgic vibe. Take notes; you’re going to want to stay at one of these cool motels on your next road trip.

The Vagabond Motel Was The Stomping Grounds For The Rat Pack

The Vagabond Motel Was The Stomping Grounds For Rat Pack
Emily Padura/Pinterest
Emily Padura/Pinterest

Considering the Vegabond Motel in Miami, Florida, used to be the stomping grounds of Rat Pack members Frank Sinatra and Sammie Davis Jr., you best believe it is beyond cool! And because of their frequent stays, the owners of the 1950s-style motel kept its charm during the 2014 facelift.

The rooms featured throughout the motel are everything a Miami vacationer could ask for. With pops of Miami-appropriate colors of pink, turquoise, and yellow, the rooms feature era-friendly geometric stenciling on the walls and vintage light fixtures, giving the home away from home a modern 50s vibe. It feels as though Sinatra would be lounging by the pool!

The Wigwam Motel Resembles Native American Teepees

The Wigwam Motel Resembles Native American Teepees
Carol M. Highsmith/Buyenlarge/Getty Images
Carol M. Highsmith/Buyenlarge/Getty Images

Located in Holbrook, Arizona, the Wigman Motel is one of those funky places you read about but never think to stay. Well, we’re here to tell you you should definitely add it to your road-trip list of places to do an overnight. Why? Each of the motel’s rooms is designed to resemble the teepees built by the Plains Native Americans.

Right off the Historic Route 66 highway, the Wigman Motel is so much more than just its quirky rooms. This lodging attacks visitors for another reason: the vintage cars that are always parked on the property.

Pioneertown Motel Is Straight Out Of The Wild West

Pioneertown Motel Is Straight Out Of The Wild West
Hannah Greene/Pinterest
Hannah Greene/Pinterest

Founded in the 1940s by King of the Cowboys, Roy Roger, the Pioneertown Motel in the California desert has been the backdrop of more than 50 Hollywood Westerns. Considering the lodging looks like it is straight out of the wild west, the location for the films makes total sense!

While the motel has since gone under renovations since the 40s, the weathered clapboard siding allows it to maintain its rustic charm. One of the newer amenities offered to guests is an upper-level deck overlooking the Pioneertown Mountains Preserve. The perfect place to sit with a cup of coffee and book.

The Red Caboose’s Rooms Are Individual Train Caboose

The Red Caboose's Rooms Are Individual Train Caboose
John Greim/LightRocket via Getty Images
John Greim/LightRocket via Getty Images

In 1970, Donald M. Denlinger cut the ribbon and opened the 19 cabooses that made up The Red Caboose Motel in Ronks, Pennsylvania. Since then, the motel has grown to 38 carts, including a baggage car and a mail car, each decorated to represent a famous American railroad.

And, yes, guests do stay in one of the cabooses, as they are actually the rooms! We can talk all day about how the motel offers movie nights in a nearby barn, or how you’ll get some country cooking at the restaurant. But, come on, the motel is literally a train.

Each Room At The Dive Inn Has A Different Theme

Each Room At The Dive Inn Has A Different Theme
Leslie Gengo/Pinterest
Leslie Gengo/Pinterest

The Dine Inn Motel located in Nashville, Tennessee, isn’t your typical lodge. Each of the 23 rooms featured at the establishment is themed differently, from 60s rustic to 70s stripes. Unless you ask, you never know what you’re going to walk into! And that’s not even the best part.

Each room is equipped with a “Party Switch” that releases a disco ball. That’s right; who says disco’s actually dead? Each “switch” comes with four themed song channels, depending on your mood. Of course, if you feel like getting out of your room, there is also a dive bar on site.

Big Texan Makes Sure Guests Know “Everything’s Bigger In Texas”

Big Texan Makes Sure Guests Know
Renae Reed/Pinterest
Renae Reed/Pinterest

Located on the famous Route 66 highway, the Big Texan Motel, located in Amarillo, Texas, looks like the set of an old Western Film. Just on the right side of kitschy, this motel takes the phrase “everything’s bigger in Texas” and totally rolls with it in the best way possible.

From swinging salon doors in rooms to a Texas-shaped pool in the back, this motel should be on every John Wayne-enthusiasts bucket list. Opened in the 1960s, the Big Texan is known for its old-timey charm and old-fashioned wooden furniture.

Sound View Greenport Is Located On A Private Beach

Sound View Greenport Is Located On A Private Beach
Tinaberbina/Pinterest
Tinaberbina/Pinterest

Located on a private beach of the Long Island Sound in North Fork, New York, the Sound View Greenport is the perfect place to relax. The motel boasts 55 bright and airy rooms on a quarter-mile stretch of private beach. Yea, most people get used to the luxury!

While the rooms are something to be admired with their modern amenities and furnishings, a big draw is the food and drinks. The property has a few different dining options, including a seafood restaurant headed by an award-winning chef. But if mellow is more your style, there is a beach bar located directly on the sand, complete with tiki torches and a bonfire.

Beck’s Motor Lodge Is Located In The Historic Castro District

Beck's Motor Lodge Is Located In The Historic Castro District
Laura Ronspiez/Pinterest
Laura Ronspiez/Pinterest

While Beck’s Motor Lodge In San Francisco, California, isn’t renting out rooms for five dollars a night anymore, it is still a historically-significant location. Built-in 1958 in The Castro district of the city, the lodge had front-row seats to one of their residents making history, Harvey Milk, the first openly gay politician.

The night he was killed, Milk’s supporters held a candlelight vigil, marching right past Back’s Motor Lodge’s front door. If you’re interested, the lodge has an amazing upper deck where you’re able to lounge back, watch the San Francisco fog roll by, and read up on some of the district’s LGBTQ+ history.

Austin Motel Loves Its Events

Austin Motel Loves Its Events
Joe Scarnici/Getty Images for Culture Trip
Joe Scarnici/Getty Images for Culture Trip

First opened in 1938 and re-imagined in 2017, the Austin Motel in Austin, Texas, is a one-stop-shop for comfort and culture. Encompassing the vintage vibe of the motel is none other than the 1950s-style diner, Joanne’s Fine Foods, that is attached to the lodging.

Honestly, with the vintage phones, radios, and bright orange, and blue vinyl accents in each room, the Austin Motel feels like you traveled back in time. And if you’re one for culture, the motel hosts a slew of events around its kidney-shaped pool and throughout its hip outdoor seating area, such as “Endless Sundays” and “Full Moon Swims.”

The Dog Bark Park Inn Resembles A Giant Beagle

The Dog Bark Park Inn Resembles A Giant Beagle
Ace Everett/Pinterest
Ace Everett/Pinterest

Have you ever dreamed of living in a dog house, like literally a house shaped like a dog? Well, now is your chance! The Dog Bark Park Inn, located in Cottonwood, Idaho, was designed in 1997 and is considered the “World’s Biggest Beagle.” Sorry, locals call the beagle Sweet Willy, so we’re going to follow suit.

Imagined by local artists Dennis and Frances, Sweet Willy makes going to the doghouse quite an adventure. The motel features one room, a loft, and a cozy nook in the muzzle. And let’s not forget bout the fire hydrant port-o-potty located outside of Willy!

Thunderbird Inn’s “Refrigerated Rooms” Attracted The Jackson 5

Thunderbird Inn's
Richard Hennessee/Pinterest
Richard Hennessee/Pinterest

Built in 1964, the Thunderbird Inn in Savannah, Georgia, offers more than a bright neon sign and Moonpies and RC cola on the nightstand. This inn offers something other lodgings lacked back in the day, air conditioning! The “refrigerated rooms” attracted many travelers, including the famous group the Jackson 5.

After undergoing a revamp in 2018, some aspects of the inn were changed, but none of its charm or southern hospitality. Now guests are welcomed with warm popcorn and complimentary Krispy Kreme donuts, with other treats awaiting them in their rooms. Needless to say, this southern peach accommodation is bringing out all the stops when it comes to yummy snacks.

Jupiter Motel Was Revamped By Locals

Jupiter Motel Was Revamped By Locals
Holly Thoms/Pinterest
Holly Thoms/Pinterest

Located in Portland, Oregon, the Jupiter Motel was once located on a not-so-nice street. Thanks to the help of local artists and do-gooders, the unmistakable 60s lodge has since been revamped from its sketchy roots. And when we mean locals, we mean it wholeheartedly.

Each room’s headboard murals are thanks to local artist Beth Kerschen, while the bedding is courtesy of Portland-based store Seek & Swoon. Guests also don’t have to travel far for good food or drinks, as the Doug Fir Lounge is right next door and offers live music every night.

Modern Hotel & Bar Has A Collection Of 45s In The Bathroom

Hotels in Boise, Idaho_ The Modern Hotel and Bar - Let's Go Boise, Idaho
Brooke Rice/Pinterest
Brooke Rice/Pinterest

Since Boise, Idaho, has a reputation of being “little Portland,” it’s only fair that the city has a hipster motel that thinks of itself as a hotel. The Modern Hotel & Bar is the flannel-wearers, wanderlust lovers, and mustache growers dream lodge. First opened in 2007, the motel quickly earned a name for itself as one of the hippest around.

While the rooms are cozy with retro-chic lighting and mid-century modern furniture, it’s not the reason people are attracted to the place. This motel’s “cool factor” comes from the impressive collection of 45s in the lobby bathroom, as well as the local DJs that come to play.

The Anvil Hotel Has A Ski-Lodge Feel

The Anvil Hotel Has A Ski-Lodge Feel
The Egg Out West/Pinterest
The Egg Out West/Pinterest

At first glance, The Anvil Hotel in Jackson, Wyoming, looks like it time-traveled back to the wild west. Complete with metal bed frames, milk-glass globe sconce light fixtures, beadboard wall paneling, and gleaming brass hardware in the bathroom, the rooms are nothing if not minimalistic. Yet, they have a very comfortable ski-lodge feel.

With the dark wood of the Instagram-worthy Italian restaurant and bar Glorietta, this motel is the perfect stop for those on their way to Yellowstone National Park. Or, if local attractions are more interesting to you, there is plenty to see in the town of Jackson, including hiking, arts festivals, and more!

The Astro Motel Is Vintage In All The Right Places

The Astro Motel Is Vintage In All The Right Places
Sandy Moyer/Pinterest
Sandy Moyer/Pinterest

The Astro Motel, located in Santa Rosa, California, is just a skip away from the hip downtown area. But let’s focus on the cool motel first, as it is vintage in all the right places. With quirky curvy lines, a color palette of turquoise and pumpkin, and minutes away from multiple trails, this motel is a cyclist-enthusiasts dream destination.

We say cyclists and not all travelers because this 1963 motel is set right in the heart of one of the premier cycling destinations, located minutes from The Santa Rosa Creek Trail. As a bonus, the motel has Shinola Bikes available for guests to rent.

The Calistoga Motor Lodge & Spa Has A Mix-Your-Own-Mud Bar

The Calistoga Motor Lodge & Spa Has A Mix-Your-Own-Mud Bar
Rachel Einsidler/Pinterest
Rachel Einsidler/Pinterest

Located in Calistoga, California, the Calistoga Motor Lodge & Spa is the state’s ode to the old-fashioned great American road trip. Complete with retro-inspired decor, this 50-room motel is every bit as fun and vibrant as it was back in the 40s when it was built.

But this motel isn’t like the rest, as they pride themself for their quirky amenities, such as their mix-you-own-mud bar and spa. The latter of which has claw-foot tubs on white, mustard, blue, and mint green tiled floors. A hot lather with the detoxifying with medicinal salts from Turkey, New Zealand, and Japan is what every road-tripper needs!

Inn At The Commons Is A Fresh Produce Lovers’ Dream

Inn At The Commons Is A Fresh Produce Lovers' Dream
Pinterest
Pinterest

Originally opened to travelers in the 1960s, the Inn at the Commons is a hidden treasure. Located in the southern town of Medford, Oregon, the motel is a retro-lodged located in the heart of the state’s fruit belt, a haven for any local producer lover.

The inspiration for the motel’s colorful hue comes from the surrounding pear orchards, fruit that is readily available for guests at the closely located Rouge Valley Farmer’s Market. Also within walking distance of the inn is Buttercloud Bakery. Now, you’re contractually obligated to go to this bakery and order one of their homemade biscuit sandwiches; you won’t regret the decision!

The Roadrunner Lodge Motel Plays 60s Hits

The Roadrunner Lodge Motel Plays 60s Hits
Tia Callas/Pinterest
Tia Callas/Pinterest

Starting off as two separate properties, the combined Historic Route 66 attraction The Roadrunner Lodge and Motel in Tucumcari, New Mexico, is a humble slice of classic America. Even though the motel has had a facelift since its original opening, owners Amanda and David have done their best to keep the retro-feel of the motel alive.

You’ll get the feeling that you traveled back to the 60s right away, as they play radio hits and commercials from the era. Not to mention their “Snazzy 60s” rooms come equipped with some of the best toys and board games from the time!

Unscripted Durham Turned Into A Boutique Hotel

Unscripted Durham Turned Into A Boutique Hotel
Emily S/Pinterest
Emily S/Pinterest

The 1960s motel, known as the Jack Tar Motor Lodge in Durham, North Carolina, had a huge revamp back in 2017. Not only did the decor, amenities, and overall aesthetic of the place chance, but so did the name. The Unscripted Durham is now thought of as more of a boutique hotel than a roadside motel.

Each room has a modern feel with sleek lines and designs but sports a retro color-scheme with its geometric patterns of teal and orange. But with a coffee bar and swanky roof-top pool, this place is far from the 60s motel that once graced the streets of downtown Durham.

The Caliente Tropics Resort Is Simply Paradise

The Caliente Tropics Resort Is Simply Paradise
Keith May/Pinterest
Keith May/Pinterest

One frequented by the likes of Frank Sinatra and Sammie Davis Jr., The Caliente Tropics Resort is everything a guest needs during their trip to Palm Springs, California. A product of the 60s, the swanky hotel now boasts various modern amenities to attract people frequenting the hot weather of the Springs.

Of course, we’re talking about the gorgeous pool and bar located on the hotel’s grounds, surrounded by palm trees and overlooking the picturesque San Jacinto Mountains. Add on the modern features adorning every room, and you have the perfect mix of luxury and simplistic tiki-getaway charm.