I would also like to encourage everyone to head over to iTunes and download the studio version of "Winter Wonderland" from this year's A Very Special Christmas collection which benefits the Special Olympics. More details here.
All I Want for Christmas is Us, feat. Tristan Prettyman (Studio Version)
All I Want for Christmas is Us, feat. Tristan Prettyman (Live Version)
Happy Holidays 2009
Have Yourself a Merry Little Christmas (feat. Jessie Payo)
Have Yourself a Merry Little Christmas (Colbie Caillet feat. Jason Mraz)
Merry Holidays (Video Rip)
Oh Come All Ye Faithful, feat. The Voices of Prayz (Video Rip)
The Christmas Song (Chestnuts Roasting on an Open Fire)
Traditional Christmas Bell Song
Winter Wonderland (live)
And for full-on Holiday joy, head over to Archive.org and download the entire "Christmas Pageant Show" live from Twiggs back in '06 in lossless audio. You won't be sorry. You can also stream it from there if converting files gives you a headache.
As always, I'd love a comment if you're grabbing anything and if there's something missing here let me know.