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100 Orchard St., New York, NY 10002, United States

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.

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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.