Courtesy of The Phoenix Hotel

Original artwork, retro-chic amenities, and (sometimes) comfortable accommodations define these bastions of cool.

Phoenix Hotel, San Francisco

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Some of the modern hipster’s most revered icons, from David Bowie and Johnny Rotten to Vincent Gallo and Johnny Depp, have holed up at the kitschy-chic Phoenix, a former roadside “no-tell” set in San Francisco’s still-gentrifying Tenderloin District. The hotel’s ultimate concept is based on Rolling Stone Magazine, and—to that end—owner Chip Conley lures traveling musicians and rock band managers with discounts and free massages, a model that’s been replicated by hipster hotels around the country. jdvhotels.com

America's Coolest Hipster Hotels

Phoenix Hotel, San Francisco

Some of the modern hipster’s most revered icons, from David Bowie and Johnny Rotten to Vincent Gallo and Johnny Depp, have holed up at the kitschy-chic Phoenix, a former roadside “no-tell” set in San Francisco’s still-gentrifying Tenderloin District. The hotel’s ultimate concept is based on Rolling Stone Magazine, and—to that end—owner Chip Conley lures traveling musicians and rock band managers with discounts and free massages, a model that’s been replicated by hipster hotels around the country. jdvhotels.com

Courtesy of The Phoenix Hotel

America's Coolest Hipster Hotels

At Longman & Eagle, a tiny inn set in Chicago’s artsy Logan Square neighborhood, it’s pretty clear you’re in hipsterdom the moment you check in. You pick up your key from the bearded barkeep at the downstairs gastropub, then head to a room with a custom wall mural, a (modern) Apple TV, and a (retro-cool) cassette player.

Related: America's Best Cities for Hipsters

You generally know a hipster hotel when you see it—like Longman & Eagle, it’s most likely located in an up-and-coming neighborhood and filled with amenities that appeal to a creative-minded and tech-savvy clientele. Retro, of course, reigns. And staffers, who might include a resident DJ or tattoo artist, come clad in the latest downtown-hip fashion.

The modern hipster hospitality phenomenon traces back to the Ace Hotel, a pioneering brand owned by Alexander Calderwood that opened its first property in Seattle in the late ’90s (its fifth outlet will open in L.A. in fall 2013). Its name references the playing card, either the highest or lowest in the deck, and every Ace establishment offers a hierarchy of accommodations: from budget, hostel-style rooms—where there’s a shared bathroom down the hall—to indulgent, rock star–style pads, with turntables and customized Gibson guitars.

It appears that Calderwood, along with fellow trailblazer André Balazs—who opened the first Standard in Hollywood in 1998—tapped into something of a cultural zeitgeist. Today, more and more hoteliers are jumping on the budget boutique bandwagon, opening properties that range from the industrial and retro-mod to the avant-garde and cutting-edge, and even to the downright quirky.

Some hotels also embody the ethical, artisanal mind-set of modern-day hipsterdom. At the Wythe, in Williamsburg, Brooklyn, much of the old wood was salvaged and repurposed—the building once housed a textile factory—for a classic urban warehouse look. The restaurant specializes in sustainable “whole animal wood fire cooking” and sources all ingredients from local New York farmers and producers.

Things are a little less precious inside San Francisco’s Hotel des Arts, where rising stars from the underground and street-art scene had full creative license over most of the accommodations. Design motifs in the tiny rooms include wild techno-punk patterns, whimsical Japanese anime, and trippy “Southwest Voodoo” murals.

One of the most requested rooms here includes an installation by artist Anthony Skirvin, who was inspired by obsessive-compulsive disorder and the hoarding of worthless objects. Expect a lot of random clutter, along with the very clear sense that you’re checked in to a true hipster hotel.

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