My sister and I went last year. We had a different hotel every 2nd night or so in the different areas. We spent 2 days in the North Loop, and 2 days in the South Loop, and 2 days in the Tetons. There is so much to see I don't think you could be disappointed no matter what you saw. In whatever area you're in, you might want to hit the main attractions first and decide from there what else interests you. We drove into the West entrance after spending a day in Banack which is a deserted gold mining town (my sister likes to photograph, and she got some great pictures of the abandoned (but kept up as a sort of museum) buildings). We drove out the East (?) entrance because we wanted to hit the famous highway (I think where Red Lodge is that someone mentioned). Our trip started on Aug 30th and we left on Labor Day from Billings where our nephew was getting married. The crowds weren't too bad at that time and we had a fantastic time.