I recommend staying in downtown Lexington, so you can walk everywhere and explore the city. Just be aware that in May, your options may be limited with graduations occurring at both Washington & Lee and VMI. My two top choices include:
Robert E. Lee Hotel: This is an historic hotel featuring 39 rooms and suites. Built in 1926, it was totally restored in 2014. It is located at 30 S. Main, which makes it an easy walk to all of the downtown sites and restaurants. Its Rocca Bar Ristorante gets very good reviews.
The Georges: A small boutique hotel located in two historic downtown buildings. The Washington Building, dating from 1789, has five suites, and the Marshall Building, at 11 North Main, was built in 1809 and has 13 guest rooms and suites.
The Georges has two great dining options:
Haywood’s: The piano bar restaurant features locally sourced, seasonal cuisine and nightly entertainment. I enjoyed my dinner listening to the music. I enjoyed a house salad, lovely salmon entree and a local hard cider.
Taps: Taps is their lobby lounge featuring craft beer, creative cocktails, soups, salads, sandwiches and snacks with a Southern emphasis and local ingredients from farms throughout the Shenandoah Valley.