Relive the flophouse scene from Drugstore Cowboy (parts of which were filmed here in 1988) at the Ace Hotel (from $95), a newcomer to downtown’s Pearl District. Rooms are tiny but stylish with scratchy Pendleton Woolen Mills knits, murals by local street artists (Brent Wick’s giant cat room is a favorite), and iPod docks and turntables.
See Portland’s version of a rock-and-roll hotel—a mantle held by the Chateau in L.A. and the Chelsea in New York—at Jupiter (rooms from $114), a sixties roadside motel gone fastidiously mod. After catching an indie-rock show at the attached Doug Fir Lounge, join the after-party spilling over into the driveway.
For more peace and quiet, try the less cool but just as comfy McMenanins Kennedy School (from $99) in working-class Northeast Portland. On the site of a former elementary school, the property now includes adult pleasures like a soaking pool, a brew-n-view (i.e., a movie theater that serves beer), and a brewery.