"Bed & bath: Studio, 1 bathTop amenities: Incredibly close harbor viewsNearby attractions: All the shops and restaurants Oak Bluffs has to offer—but especially Back Door Doughnuts One of the best parts of visiting an island is observing daily life, and the comings and goings of its inhabitants. This studio, located on a pier in Oak Bluffs, is in the literal center of the action. If offers excellent harbor views—“You cannot get closer to the harbor unless you fell in,” reads the listing—and there’s even room service (of sorts): This studio is located on top of the Lobsterville Bar & Grille, which will deliver to you. Book now with Airbnb" - Todd Plummer