Okay, so it's not technically at Monticello — but it's not far away, either. Located just a few miles from Thomas Jefferson's celebrated residence, Keswick Hall at Monticello is one of the premier places to stay in Central Virginia. Built in 1912 as a villa for a couple looking to recreate their recent Italian vacation, this mansion is home to 48 rooms and suites, as well as multiple restaurants and bars, a spa, a tennis and aquatics center — including a 25-meter infinity Pool — a championship golf course, and a club. With the University of Virginia, charming Charlottesville, and over 25 wineries and breweries nearby, there's plenty to keep you occupied.