Holiday? I'm pretty sure those songs are specifically for CHRISTMAS.
I generally think of Christmas when someone says "the Holidays", but that may just be me. You can't please everyone when it comes to celebrations like Holidays.
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Yes. Truly, there is no more traditional, clearly Christmas song than "Duck the Halls." (That is, by the way, not a typo.)
Of course, that's irrelevant. "Holiday" includes "Christmas."
EDIT: I do not want to make any off-topic replies to future posts, so I'll just edit this one to say that it is quite clear what "holidays" means when said in the November-December timeframe, at least in the United States. That is simply how the word is used, and you should deal with it. (If you insist that this iTunes playlist could be a Flag Day playlist, you are obviously simply being an uncooperative communicator.)
If this was reddit, you'd have an upvote, my friend.