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1. SleepAfloat Houseboat 1 Pier Eight, Charlestown, MA 02129 (Charlestown)

Why stay at a hotel on the water when you can channel your inner-Sonny Crockett and stay on the water, thanks to this "fun and funky" Airbnb houseboat that sleeps six, rocks exposed beams and dual decks, and is docked in a Harbor marina that's within walking distance of both downtown and Old (but-not-Michael) Ironsides.