How about Hot Buttered Rum by the Red Clay Ramblers? Christmas is mentioned, but winter is the subject. Or maybe love.
What, and nobody’s mentioned Auld Lang Syne yet?
But the feast of Saint Stephen falls during the Christmas octave, and so it’s certainly a carol of the Christmas liturgical season. A similar example is the Coventry Carol, which relates to the massacre of the Holy Innocents (feast day 28 December).
Any suggestions of CDs for an anti-ipod luddite? I have about 20 XMas CDs of which I like about 10 of them, the latest being Adventions:
To give you an idea of what’s in rotation, we have a two Windam Hills Winter Solstice (V and IV), Music to drive the cold winter away, Christmas Island, Crosby Sinatra Cole, Hawaiian Slack Key Guitar, Charlie Brown,.
Any good/eclectic/classic suggestions?
Fountains’s Adam Schlesinger also co-wrote a funny Hanukkah for the Stephen Colbert Christmas special called Can I Interest You In Hannukah? (“THEY ARE CANDLES!” makes me laugh every time.")
I like “Hannukah Blessings” by the Barenaked Ladies, off their Barenaked for the Holidays album; it’s rather melodic and moving. On that album, they also do “Hannukah, Oh Hannukah” and “I Have a Little Dreidel”, plus a rendition of “Auld Lang Syne” for New Year’s. The song “Snowman” off that album is a melancholy look at a snowman’s life.
On that thought, I added Elvis Costello’s “(What’s So Funny 'Bout) Peace, Love, and Understanding” to my Christmas playlist.
Three Dog Night’s “Joy to the World” is a fun alternate “version” of the song to substitute. 
I’ve Got My Love To Keep Me Warm (Irving Berlin), sung by Sinatra and others.
A Winter’s Solstice, in all of its various incarnations.
The Long Long Winter Night, Edvard Grieg
In Gabriel’s Garden, Wynton Marsalis: this isn’t Christmas (or even winter music, for that matter), but it makes you think of the season anyway. It’s all brilliant trumpet work on baroque classics.
The Four Seasons (winter portion), Vivaldi