Let me preface this by saying I worked in records stores for five holiday seasons. "Burned out" doesn't begin to describe it. Nonetheless, there are a few that still give me happy feels even after hearing them a few hundred gazillion times.
1. "A Snowflake Fell (and it Felt Like a Kiss)" - Glasvegas
One of those "the next big thing bands that wasn't" (and that's a long, long list, isn't?), Glasvegas borrowed liberally from the best of the Jesus and Mary Chain. This is a vaguely holiday-ish song that's much prettier than it had any business being (especially since it was released on the same EP as "Fuck You, It's Over.")
2. "2000 Miles" - The Pretenders
Even though I'm an 80s person, I was never much of a Pretenders fan. This song, though, stands head and shoulders above most holiday offerings. It's catchy and it isn't cloying. Faint praise, maybe, but it has never made me cringe and that can be said of very few holiday songs.
3. "Christmas in Hollis" - Run-DMC
Fun holiday songs are the worst. The forced frivolity is magnified to unbearable levels during the holidays, but if anyone can pull it if, it's Run-DMC. It's miles from their best work, but I always grin when I hear it. It's the antithesis of Paul McCartney's song-that-will-not-be-named-here.
4. "Just Like Christmas" - Low
I like their sound, ok? Most of my Christmases growing up were spent in Kansas and this song makes me think of cold winds on prairies even though its not about that at all.
5. December (entire album) - George Winston
Solo piano versions of standards sounds about as trite as it gets, but this album is THE gold standard for holiday records in my opinion. When we'd play it in-store at the record store, we'd sell out of it every time. Utterly sentimental and absolutely timeless.