This island on the New York-Canada border isn’t just a lovely place to vacation during the warmer months—it’s also got a lot of history. During Prohibition, it was the staging area for a robust booze-smuggling operation. Today, Whiskey Island is a rustic three acres of natural beauty and historic charm. It recently sold to new owners, but it’s still rentable for about $10,150 a week, which breaks down to $1,450 a night. It sleeps 15, so it’s potentially as cheap as $97 per person per night. It’s a terrific spot for fishing, swimming, and boating—it’s only accessible by boat, actually. One thing to note is that the house isn’t heated, which means you’re not going to be renting this island in the winter.