God yes, all the time. Navigation was more of an art than a science back then. And you have to imagine you’re flying quite high to avoid flak, while looking out for targets that might be obscured by cloud cover and where the lights were turned off so as not to present a clear target for said bombers.
Basically, the crew dropping the bombs might be ‘reasonably certain’ they’re hitting the right target, but a few miles here or there can make a lot of difference. You think you’re looking at A, while you’re really flying over B.
I live in the Netherlands, right on the German border. A local village here was bombed by accident on february 15th 1945, because the bomber crew mistook it for a German industrial complex just over the border. They dropped 35 bombs. They luckily ‘only’ killed 2 and injured 7. There’s a yearly memorial.
It’s terrible that it happened, but honestly… you really can’t blame the crew for it.