Blue Moon Hotel

Set on the Lower East Side's main thoroughfare, this 22-room brick guesthouse—originally built as a tenement in 1879—perfectly embodies its quirky, eclectic home neighborhood. Though updated with modern-day amenities like whirlpool tubs, Wi-Fi, cable TV, and mini-fridges, the rooms (all named after old movie stars and jazz giants) still retain details from their historic past—like wrought-iron bedsteads and original wood shutters, window moldings, and (in some cases) window settees. It's no wonder the place is a hit with today's crop of young, scruffy-chic Lower East Siders; after all, these are the kids who prefer their techno music on vinyl, and who pair their mod asymmetrical haircuts with outfits from the thrift shop.

Tip: To get a real sense of the old neighborhood, visit the Tenement Museum, less than a block away (tenement.org); then walk over to Houston and Ludlow for pastrami at the venerable Katz's Deli (www.katzdeli.com).

Room to Book: Spring for one of the penthouse suites (the Al Jolson or the Eddie Cantor—both of which have 14-foot ceilings and enormous windows with views of Manhattan), or the Molly Picon suite, with its 26-foot-long private terrace.