One summer, there was a radio station that closed, and while it was getting ready to open the new one, it played Feliz Navidad non-stop for a month.
I was in the mall one time shopping at probably Dillard's, and they had a stereo sitting in the middle of one of the sections and it started playing Bing Crosby's White Christmas, and some guys came over to turn it off. "It's not even Halloween yet!" Laughed so hard.
Last year, I decided that I wasn't going to listen to any Christmas music until Christmas Day. And so I successfully did it.
So yeah, Christmas Day is the only appropriate time for Christmas music.
It's not that I don't like Christmas music, it's the fact that you only have 25 days to listen to it, and then the moment is gone. And in those 25 days, the same 50 songs are shoved down your throat by all the radio stations, stores, and movies you watch throughout December.
And yeah, it's completely annoying when it pops up on your iPod while shuffling it in the Spring/Summer. But thankfully you can set it up so it omits those songs.
Someone DID get fined for playing Last Christmas by Wham! non-stop one summer. I remember hearing it on the BBC news.

But it was mostly because they had it blaring out.