I think if you turn web history off it will remove all places that You have been .
I don't have it on and it is constantly telling me to put it on if I want to save time because it stores recent places etc .
In Google Maps, I don't mind deleting one at a time. What I don't like is how when I delete one, it then jumps up to the top of the list. That's ok if your deleting everything, but I only want to delete some old locations I don't need. Jumping to the top slows me down.