Classic Americana Stays Are Making a Comeback

From grand dames to roadside motels, check into these vintage-studded stays for retro style, nostalgia and contemporary comforts.

Part retro escape, part modern comfort — these hotels channel classic Americana while still feeling fresh enough for today’s traveler.

Part retro escape, part modern comfort — these hotels channel classic Americana while still feeling fresh enough for today’s traveler.

By Lindsay Cohn

Nostalgia is big business. Perhaps it’s due to our collective tech-induced overstimulation and information overload. Or maybe it’s a wistful longing for less complicated times when carefree summers were spent outside until the sun faded and we didn’t worry about the ingredients in the popsicle from the ice cream truck. “I believe it’s a reaction to our fast-paced, digital world. With so much constant change, people are finding a deep comfort in that kind of continuity that comes from connecting to a past that feels a little simpler, in some ways more certain,” JP Oliver, Managing Director of the 137-year-old Hotel Del Coronado, tells InsideHook.

Cultural anchors — whether it’s a historic hotel, classic candy or drive-in cinema — seem to be more important to the zeitgeist than ever. “People are longing for constants, for traditions, for safe places to come back to that stand the test of time, that don’t change, that help them escape the hurly burly of everyday life and bring them back to timeless moments of pure joy,” says Curtis Bashaw, Founder and Managing Partner of Cape Resorts, which operates Congress Hall, America’s oldest seaside resort. The past isn’t just in the rear view mirror, it’s front and center — driving trends, purchasing habits and bookings. 

Concepts pulled from the archives are fueling growth across many industries. Y2K fashion is all over the runway and TikTok. The market for classic cars continues to grow. Newport’s Rosecliff mansion just unveiled an exhibition dedicated to prominent Gilded Age architect Richard Morris Hunt. A recent study reveals that almost half of Gen Z are pining for the pre-Internet era. (To be clear, those of us who remember life before the web feel the pull of the past just as deeply.)

When it comes to travel, the Global Wellness Institute reports an uptick in demand for analogue experiences that prioritize human connection over screen time. Trains are experiencing a polished resurgence with the relaunch of the Orient Express (the latest journey lets riders hit the links at golf courses around Italy) and the debut of Britannic Explorer, A Belmond Train, the first luxury sleeper train in England and Wales. In June, Pan Am returned to the skies with a special transatlantic flight from JFK this year. (There are whispers of a fleet-wide reboot.)

“Today’s travelers aren’t just looking for a room, they’re looking for a sense of place. It’s a return to the grand old resorts, the classic road trip lodgings, and the kind of hospitality that feels both elegant and genuinely warm,” says Oliver. Across the hotel industry, historic grand dames are getting 21st-century upgrades, there’s an influx of new properties where nostalgia is a key ingredient and a forward-thinking generation of hoteliers has started converting old-school roadside motels and motor lodges into cool boutique haunts that pay tribute to the past in creative ways while catering to present-day tastes. 

If you’re looking for a chic place to kick back and enjoy vacation vibes unsullied by the fast-paced pressures of today, consider checking into one of these classic Americana stays. 

Grand Dames

Hotel del Coronado
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Hotel del Coronado: Coronado, California

Elisha Babcock and Hampton Story aspired to build a seaside resort that would be “the talk of the Western world.” That dream became a reality when Hotel Del Coronado opened in 1888. Over the years, the beachside crown jewel of Coronado has hosted titans of industry and Hollywood stars, appeared in films and become a symbol of the sunny Southern California lifestyle. The Victorian beauty, which completed a $550 million renovation in June,  is still the talk of the town, with terracotta turrets, stained glass windows and beach bonfires as reminders of its timeless charm.  

Ocean House
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Ocean House: Watch Hill, Rhode Island 

A blufftop respite that nods to a bygone era, Ocean House, located in the quiet luxury enclave of Watch Hill, has welcomed guests since 1868. In 2010, the yellow-and-white Victorian icon got a top-to-bottom update to bring it up to code and the high standards of discerning modern travelers. On a summer day, the toughest choice guests have to make is whether to go for a swim in the saltwater lap pool, grab a mallet on the tournament-level croquet lawn or stretch out on the serviced stretch of white sand just out front. 

Congress Hall key staff on the lawn in 1928.
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Congress Hall: Cape May, New Jersey

Established in 1816 by Thomas H. Hughes, Congress Hall is the epitome of a timeless seaside resort. Many of the charming attributes that drew visitors to the prominent Cape May landmark back then persist—including its iconic yellow brick facade, which has been painted the same shade for 144 years. Guests can experience the past in the present through guided history tours of the property, sipping sundowners in rocking chairs (a classic pastime that recalls a simpler time) and snoozing in the suite named after Benjamin Harrison, who retained a summer office during his presidency. 

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The Inn on Biltmore Estate: Asheville, North Carolina

Built by George Washington Vanderbilt II in 1895, Biltmore Estate is the largest privately owned home in America and one of the most historic getaways in the South. The Inn on Biltmore Estate just wrapped a two-year renovation of its guest rooms, suites and corridors. The interiors — a mix of nature-inspired wall coverings by William Morris, embossed leathers, carved wood detailing, brass fittings and artwork from Vanderbilt’s personal collection — are enhanced by views of the Blue Ridge Mountains. 

Ponte Vedra Inn & Club at night.
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Ponte Vedra Inn & Club: Ponte Vedra Beach, Florida

The grand dame of Florida’s northeast coast, Ponte Vedra Inn & Club (which will celebrate its centennial birthday in just three years) is a living legend. So much so that the town was named after it. There’s a distinct Sunshine State vacation vibe about the five-star property with its ocean vistas, sophisticated seaside ambiance and lengthy list of amenities that put it on par with a private country club. It also boasts a championship golf course, tennis courts, four swimming pools and a posh spa for facials, massages, and body wraps. 

Converted Motels

The Beachside
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The Beachside: Nantucket, Massachusetts

Billed as a love letter to the great American summers of the past, The Beachside brings joy and retro charm back to Nantucket. A place for families to make popsicle-stained memories, the new and improved boutique hotel has a swimming pool, a lawn for barefoot frisbee and cornhole, an arcade for analogue entertainment and slushies to cool down. It offers a roster of nostalgic programming, from crafts to outdoor movie nights. There’s also a curated shop stocked with artisanal snacks and vintage-inspired merch, as well as complimentary bikes to cruise around town. 

The Surfrider
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The Surfrider: Malibu, California 

A roadside motel revamped into a chic, contemporary crashpad and a mandatory stopover on any Pacific Coast Highway road trip, The Surfrider takes a SoCal-inspired approach to modern minimalism. It gives off the vibes of staying at a stylish friend’s beach house. Rooms are flooded with natural light and swathed in airy neutrals, streamlined furnishings and sisal rugs. The mellow guest-only rooftop invites weary travelers to pause for cocktails and stunning panoramas before clocking more miles. 

Hotel Marina Riviera
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Hotel Marina Riviera: Big Bear​, California 

The opening of Hotel Marina Riviera in June marks the rebirth of a lakeside landmark and gives Big Bear-bound travelers a cool waterfront respite to call home for the weekend. The revived lodge dips its toe in the past and present simultaneously, references its mid-century roots while injecting plenty of modern mountain charm. The original Viking-inspired architecture is bolstered by wood-clad guest rooms featuring nature-themed art, a cozy all-day pizza joint and some relaxation-meets-wellness essentials—a year-round heated pool, cold plunge, and barrel sauna.

Skyview Los Alamos
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Skyview Los Alamos: Los Alamos, California

Fans of vino and vintage vibes will flip for Skyview Los Alamos, a revamped roadhouse just off Highway 101 in the heart of Santa Barbara wine country. Sitting on five acres, the hilltop hideaway pays homage to its past. The 1950s pool was restored and the original motel sign remains. Hardwood floors and leather club chairs lend even more classic character. The property also has a working vineyard and produces terroir-driven wine that pairs perfectly with the farm-fresh California cuisine.

Amigo Motor Lodge
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Amigo Motor Lodge: Salida, Colorado

First built in the 1950s and rehabbed by Texas natives Philip and Kaitlyn Sterling in 2016, Amigo Motor Lodge is a blend of easy-going and cool, enhanced by the majesty of the Rocky Mountains. The rooms and refurbished Airstreams are individually decorated in a minimal style with concrete countertops, birch bed frames, American flags and potted plants. Though you’re not likely to spend that much time inside when hiking trails, fishing, whitewater rafting and natural hot springs are outside. 

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