For childhood nostalgia: "Holly Jolly Christmas" - Burl Ives. The entire Rudolph the Red Nosed Reindeer soundtrack is special for me, all those songs were burned into my brain as a child.
For quality and production: "Merry Christmas Darling" - Karen Carpenter. Her voice was pure and amazing.
For novelty: "Santa Baby" - Eartha Kitt. The Madonna version is pure crap.