Bing Crosby and David Bowie - The Little Drummer Boy/Peace on Earth. This inter-generational classic was shot just a few months before Crosby died. It was Bing's kids who suggested Bowie for the duet. It's just fantastic.
Christmastime is Here from a Charlie Brown Christmas - Hauntingly beautiful and chock full of oh so warm childhood memories.
The Christmas Song by Nat King Cole - One of my favorite orchestrations of a song, lyrics capturing a true family holiday and the utter coolness of Nat.
The next two go together. Just before all the merriment dies down and we move to the reason for the season, we get close to the end of the day on Christmas Eve and the hour that God becomes man, born as a child, to wash us of our sins, O Holy Night, the dénouement of the story with the song reaching it's final praiseful cresecendo when indeed the Savior is born. This version, is by artist Josh Groban.
And finally, as the Savior is born and resting in his manger, we know must become very quiet, reflect, be with those we love and fall into adoration of Him and feel the peace embedded in Silent Night (the story of it's composition is a blessing itself). Having once sang this song at midnight, Christmas Eve, on the steps of a 200 year old church in New England at five below zero, it will always signify the coming of Christmas to me. Here is the song in both it's original German as well as English versions.
There are many, many other holiday themed songs and multiple recordings of such that I enjoy. I hope you enjoy my favorites here though. I would be delighted if you commented and noted some of yours.