Jean-Michel Basquiat's loft
New York, New York -- $650/nt
Billed as a "Crazy Fab" loft on the "hippest" street in NYC (O…M…G!!!), this sprawling two-bedroom-plus-studio-alcove, one-bath SoHo space was the early '80s home of famed artist Jean-Michel Basquiat. It rocks hardwood floors, a massive kitchen, and tons of light. Reportedly, Madonna also crashed here for a couple of weeks once. So there's that, too. If you only need/ can afford the studio portion, you can rent just that bit for $275/nt (but you'll have to share a bathroom with the owners).
Local tip for travelers
: Blend in with Manhattanites by treating sidewalks like freeways (pass on the left!), pronouncing "Houston" Street like "House-ton", and ordering off-the-menu classics at cool restaurants.