Winchester is a city in Franklin County, Tennessee.
Nashville is the cheapest way, it is a 2 hour drive and has many flights all around the country. Chattanooga is another alternative and is about 1 hour away. It is a small airport with small planes flying to about 7 hubs, but that is it. Huntsville Regional is a 45 minute drive South down a few country roads.
Your best bet is to rent a car at the airport, but it is possible to walk a couple of areas.
Tims Ford Lake! Rent a boat or jet skies or go swimming at a beach.
Many Dollar Generals and a Wal Mart!
Pretty much every restaurant is a chain (especially along Dinah Shore Blvd. and College St.), but drive 10 minutes to Cowan and go to Sernicolas for some good Italian.
San Miguel Coffee Co., A gorgeous ambiance an wonderful food. Offers soups, salads and grilled Italian paninis
Skips Grill on David Crockett Highway offers short order variety and non-chain taste.
Try Arezzo's on the Square for upscale dining and decent Italian food.
Best Western, 1601 Dinah Shore Boulevard.
Winchester occupies a central position in Tennessee, and is therefore within driving distance of several large cities and attractions.