Seeing that I am not a huge fan of Christmas Music, I do like some of course but I honestly cannot abide the constant playing of it from October to December!! My custom has always been to begin playing Christmas Music a week or so before the event, that way I do not tire of it (and I don't play it on repeat!!).
There's a few Classic Christmas albums like Spector's 'A Christmas Gift For You', 'The Beach Boys' Christmas', B.B. King's 'A Christmas Celebration of Hope', The Blind Boys of Alabama's 'Go Tell It On The Mountain', 'Dig That Crazy Christmas' by Brian Setzer Orchestra, any Johnny Cash Christmas album, but the one I like coming back to is Nick Lowe's 'Quality Street'. It only came out two years ago and although not a smash hit as such, for me it will be always be considered one of the classic Christmas Albums.