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The Hotel Chelsea is one of the city’s most notorious landmarks, a hotspot brimming with character even as it sinks into old age. Sid Vicious fatally stabbed his girlfriend here in 1978; Arthur C. Clark’s 2001 and parts of William S. Burroughs' "Naked Lunch" were drafted here. The Hotel Chelsea was also the one-time home to such luminaries as Jimi Hendrix, Janis Joplin, Andy Warhol, Tennessee Williams, Patti Smith, Joni Mitchell, Milos Forman, Dylan Thomas and Allen Ginsberg, to name just a few. Built as a luxury co-op in 1884, the Hotel Chelsea is perhaps equally famous for its lobby, crammed full of artwork donated by previous guests. Though the hotel is still doing double-duty as an apartment complex, (more than half of the 240 rooms are occupied by permanent residents), guests can enjoy spacious, recently renovated, soundproof rooms with high-ceilings and standard amenities. Some even come with kitchenettes and private bathrooms. The hotel is admittedly a bit run down and on the dark side, but that’s not what convinces guests to plunk down $350 a night for a suite. It’s the macabre history. And the (alleged) ghost sightings, free of charge. — Mike Sanfilippo

More rock 'n roll and literary history than one could shake a stick at.

Cons
Dismal rooms and a generally aloof staff.

 Claim To Fame
Numerous music and art world luminaries have stayed here.