Private beach access and a renovation by Brooklyn’s Studio Tack has made the Sound View one of Long Island Sound’s most in-demand stays since the 1950s. Nods to the region’s maritime past—captain chairs and wicker sofas shaped like whaling boats—are throughout. Even the 55 rooms feel like ship cabins, with cedar walls and ocean views. A modern take on Jack’s Shack, a 1935 beach concession, services the pool with seared tuna bites, while the Halyard serves fresh regional fare and North Fork wines

The duo behind Urban Cowboy hotels embraced 60’s era motel kitsch (shag carpets, leopard-print headboards, satin sheets) when they remade Nashville’s old Key Motel. A disco ball maker for Studio 54 crafted mirrored globes for the 23 rooms and a party switch lets guests set the mood to house radio channels (Sex, Drugs, Rock n’ Roll, and Sleep). The motel has a wood-paneled dive bar with a DJ booth, while a No Diving mural sets the backdrop to the pool, which becomes a hot scene in summer.

For decades, the Malibu Riviera Motel was the Bohemian hideaway along the Pacific Coast Highway. (Bob Dylan holed up in Bungalow 13 to pen “Blood on the Tracks.”) The motel received a full overhaul in 2017, and this fall, it was reimagined again as the sister property of L.A.’s stylish June Hotel. Beach-chic bungalows have been hung with photographs by the original owner, Wayne Wilcox, and a heated swimming pool—a rarity in Malibu—with poolside tacos and lobster rolls are appreciated upgrades.

The Main Street of this tiny mountain biking mecca in southern Colorado’s San Luis Valley barely stretches three quarters of a mile end to end. But there’s a lot tucked away in that span, including a new distillery, excellent bakery, and the expertly curated General Specific Store. A year-long remake of the 1940s El Rancho Motel—with vintage nods in the decor—gives roadtrippers enroute to nearby attractions like Great Sand Dunes National Park and Wolf Creek Ski Resort a reason to stay.

When Stonewall Motor Lodge opened in 1964, it catered to secret service and reporters tailing president Lyndon B. Johnson when he visited his nearby ranch. Recently restored, the L-shaped, 12-room motel in Texas Hill Country now welcomes oenophiles drawn to the region’s little local wine scene. Refreshed decor pays homage to location (Southwestern throws) and history (vintage photos sourced from the LBJ Presidential Library), and the old darkroom in Room 8 is now a kitchenette.

Silver screen stars, including Roy Rogers and Gene Autry, built this live-in movie set in the desert in 1946 so they could avoid the two-hour drive back to Hollywood while filming Westerns. The rustic exteriors look the same, but brothers Mike and Matt French modernized the interiors to once again appeal to an L.A. crowd. The 19 rooms near Joshua Tree National Park include furniture and artwork from local artisans and a communal “Canteen” stocked with books, playing cards, and organic coffee.

Stepping from the Oaxacan-tiled rooms into the tropical pool courtyard after a few frozen drinks, you may think you’re in Mexico rather than an industrial stretch of Tulane Ave in New Orleans. Outside, this two-story building still welcomes guests with an old-school neon Motel sign. Inside, the vibe is millennial cool with a lobby serving La Colombe coffee and Japanese beers and 20 simple, artful, concrete-walled rooms with Tivoli radios. A cast of food trucks services the pool, always a party.

Since 1965, the Virginian has been a respite for visitors to Grand Teton and Yellowstone National Parks, and its saloon is a classic Jackson watering hole. The dated digs get a big upgrade this January when the beloved roadside lodge unveils a top-to-toe makeover. Rooms now have bunk configurations with mid-century furnishings and Western-inspired art. A courtyard with firepits, heated pool, and hot tubs has been reimagined as the property’s social hub, and the Saloon will have craft cocktails.

A Scandi-modern update of the classic American motorlodge, this 46-room Berkshires retreat is a social hub for design-minded East Coasters looking to get back to nature. Airy rooms include sustainably-made birch wood beds, views of the Hoosic River and forest, and window nooks for posting up with a book. The 80-acre property includes hiking trails, a pool, sculpture installations, and crafts. Nearby, the MASS MoCA museum features avant-garde contemporary art in a 19th-century warehouse.

This 1920s-bunkhouse is a nod to the midcentury glory days of Upstate New York's Catskills, where city folk would congregate for the summer à la "Dirty Dancing." Airy, rustic-modern interiors include vintage Turkish rugs, plaid throws, and freestanding wood-burning fireplaces. Outdoors, there are fire pits surrounded by Adirondack chairs and a Swedish-style barrel sauna. But the best feature of the property is undoubtedly its set of stylish A-frame cabins, which open up to mountain views.