Gavin Degraw has the BEST rendition of Have Yourself A Merry Little Christmas that was released on a Target exclusive album "Songs for a Cause" in 2010. I found a live version, which is really good, but if you can find that recording... man is it chilling and loving and haunting and wonderful all in one. (Edit I found his recording it's at minute mark 3:30 to 6:32It's awesome.
Then I love Happy Holiday by Peggy Lee, this song reminds me of my mom, every time I hear it it just reminds me of her so much.
Silent Night by Five for Fighting also from Songs for A Cause. So good. My Grandma use to sing this to me when I was little.... Music is the best way to rediscover old memories! <3
Last but never least is Kelly Clarkson... Her whole new album is great. She has an incredibly classic sound to her voice which makes you feel like this is a recording of old. She has the best voice around.