Since its opening in 1915, this historic elementary school has been a beloved gem of its Northeast Portland neighborhood, near the Alberta Arts district. The McMenamin brothers renovated the then-abandoned building in 1997 and turned it into Portland’s most unique lodging. Stay in one of the 57 classrooms-turned-guestrooms (complete with original chalkboards and cloakrooms) or one of the 22 English Wing rooms, each one inspired by a book. Maybe the Ken Kesey room is your choice, or Ursula LeGuin’s namesake? At the Kennedy, guests and visitors enjoy amenities that include a casual restaurant where the kids’ cafeteria once was, cozy pubs like the Detention and Honors Bars, a movie theater with bar service and special events, saltwater soaking pool and even a working brewery set in a former girls’ lavatory.