The best area to stay in Monticello is near the downtown square, which offers convenient access to local attractions and dining.This central area around the historic Monticello Square is the town's focal point. It features several locally-owned shops, eateries, and historic buildings, making it a pleasant place for a stroll. The square itself is a landmark, often hosting community events.For couples looking for a relaxed getaway, staying near the square is ideal. You'll find charming accommodations within walking distance of places like the Monticello Railway Museum, where you can enjoy a scenic train ride, and the Allerton Park and Retreat Center, known for its beautiful gardens and sculptures.Families will also appreciate the convenience of this area. Many local parks, such as Lodge Park, are just a short drive away, offering playgrounds and picnic areas.