Where to stay
Just about any BnB or hotel on the island is wonderful. The island is shaped like a pork chop or as my Dad saw it, a baby chick. There is one main strip, Water Avenue (aka Old Harbor), that is what you see in most pictures. Most accommodations are here. Another popular section for accommodations is New Harbor.
Remember the island is 11 square miles. You’re not far from anything.
Surf Hotel, The Blue Dory Inn, The National Hotel and The Spring House Hotel are nice places to stay. The National is the white building in the above photo.
If you want a place where you can sit on a white lawn chair, put on a straw hat and stair out into the ocean as the sun sets, The Spring House is the place to be. Then again, you can dine there or just grab a chair and go to any beach and do the same thing without paying the high prices for a room.
If you don't mind the expense or have a group of friends that you can stand sharing living quarters with, you can always rent a cottage. It's the closest thing to being a resident on the island.