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America's Coolest Hipster Hotels

America's Coolest Hipster Hotels: McMenamins Kennedy School

Courtesy of Kennedy School

McMenamins Kennedy School, Portland, OR

This unique, scholastic-themed property embodies Portland quirkiness. Housed in converted classrooms—the building was once a neighborhood elementary school—guest rooms feature chalkboards, playful little water fountains, and children’s coat hooks. While the TV show Portlandia may have relegated the city’s McMenamins hospitality empire into the “over” category, the hotel’s on-site microbrewery, art-house cinema, and moody cigar lounge (called the Detention Room) are still beloved hangouts for local hipsters.

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