Bear in mind that the (mostly) US convention of referring to the "Holiday Season" is not really identifiable in Scotland, or other parts of the UK. There are songs about Christmas, and songs associated with New Year/Hogmanay, a few probably about "Yule".There are many Christmas carols, but fewer "merrymaking" songs which are still in current common use.
I appreciate that someone -probably Malcolm Douglas - is going to come along and shoot me down in flames any minute now, pointing out 30 -odd songs that I have forgotten about... anyway..
Cheers
Steven