A few resources I have found enjoyable/useful over the last few years:
In the Days of the Angels - Collection of short stories and poetry by Walter Wangerin, jr. that dig right into the heart of Christmas. A mainstay in my Christmas library.
Watch for the Light: Readings for Advent and Christmas - Daily readings for advent and Christmas that call the reader to pause and consider the Incarnation and its effect on the world around them. Includes articles and poetry from a diverse collection of men and women from modern to ancient.
The Christ of Christmas: Readings for Advent - Calvin Millers musings on the scriptures telling the Christmas story, and the people caught up in that story.
I Saw Three Ships - New to my library this year, a delightful tale of a little girl awaiting the wise men on Christmas Eve. Elizabeth Goudge crafts the story around the Christmas carol of the same name.
Accompanied by Angels: Poems of the Incarnation - A collection of Luci Shaw's poetry reflecting on the coming of Christ into our world.
Startling Joy: Seven Magical Stories of Christmas - James Calvin Schaap's unique look into the darker side of Christmas, in that each story places the reader into the midst of a crisis, a relational breakdown, a troublesome time in the lives of men and women struggling to survive the holiday season.
Folk Alley - Live streaming Americana and folk music, good any time of the year but especially lovely during the Christmas season. (note: the Christmas stream isn't up and running yet as of this writing)
Grace Cathedral - Follow the Advent worship of this church in San Francisco, renowned for its glorious music of the season. (click on the 'Choral Eucharist' link on the right side of the page)
St. Olaf Choir Christmas Festival - Always majestic, reverent, holy and fun. Nothing tops a live choir with orchestra. This is their 2008 Christmas concert.
BuynothingChristmas.org - What it says. An organization started by Canadian Mennonites, calling people to change their world and return to the heart of Christmas.
Advent Conspiracy - Calling people from consumption to compassion, encouraging less spending and more giving.