The best area to stay in Ashland is downtown, particularly around the city's central business district and along Winchester Avenue.This area is the heart of Ashland, offering a blend of local businesses, dining, and cultural points of interest. Winchester Avenue is the main thoroughfare, lined with a variety of shops and restaurants, and it's also home to the Paramount Arts Center. The area is quite walkable, especially around Central Park and the riverfront.For couples looking for a convenient and engaging stay, downtown Ashland is an excellent choice. You'll find a selection of local eateries great for a nice dinner out, and the proximity to the Paramount Arts Center provides easy access to live performances. Strolling along the riverfront or through Central Park offers a pleasant way to spend an afternoon.Families will also find downtown appealing due to its accessibility and nearby attractions. The Highlands Museum and Discovery Centre is located here, offering educational and interactive exhibits for children.