These songs are part of my holiday playlist. Although they aren't officially "holiday" songs, they all put me in the winter spirit.
Winter Song: by Sara Bareilles and Ingrid Michaelson
I love this song's message of hope, love and light in the winter... and if you have lived in northern climes, you know that message is needed in the darkest days of winter. Plus, this video is adorable.
River, by Joni Mitchell. Version by Robert Downey, Jr.
This song could definitely fit into the "Christmas bummer" category as well as the Winter category. It's a beautiful song, but super-depressing. There are also a lot of great versions, but for some reason I particularly like this version by Robert Downey Jr. from Ally McBeal.
Swingset Chain, by Loquat
Again, kind of a bummer. (Seriously. If you've lived in a snowy place -- winter can be a huge, dark, bummer). This one is about looking back to winters' past - in particular, the frozen playgrounds of childhood, and how those loves and friendships have been lost.
Walking in the Air, from The Snowman
Watching The Snowman during the holiday season is a tradition in my family. It's a sweet story, but the most magical sequence is this one, where a boy and his snowman fly through the arctic skies. Beautiful. (You might want to view this one full-screen).
Do you have a favorite winter song?