You're probably more likely to see a bundle than a straight price-drop. I expect they will just keep the price at $299 and pack-in Mario Odyssey for a while, then pack-in Metroid or something for next holiday (or whatever releases around then).
First price drop, which is almost surely going to be $50 not 100, probably won't happen until 2019 the way the system is currently going. It just passed 2.5 million units in Japan alone this week, with little signs of slowing down.
EDIT: Also I have to say, I feel the system is worth the current price. Probably my favorite Nintendo console since the N64, personally.