Ah, Ginger Snaps and Thirteen Ghosts (or Thir13en Ghosts, as the poster awfully stylizes it as). Ginger Snaps was, and is, one of my sister's favs growing up. We often had to rent movies from the library or buy in the bargain bin, and that's how she discovered that one. It's fine for what it is- a low-budget, shlocky, vageuely sapphic girl-power werewolf movie. Think I've only seen the sequels once, though, and they make the first look like a masterpiece.
13 Ghosts, while definitely falling into both campy and overly angsty early 00's shlock, fares better, in my opinion. That's one we'd watch every Halloween growing up. I still remember watching it some time in the winter for some reason, when stuck inside on a snow day, and watching the special feature of the backstory for all the ghosts. Man, we don't get special features like we used to. Supposedly they're making an anthology TV show about the different ghosts, but haven't heard anything on that in a while, so maybe it's canned. I'd still unironically take some figures from that movie.
Comfort movies/date night movies for the Halloween season? I'd say Scream, Trick r Treat, Hocus Pocus, Tim Burton's Sleepy Hollow. Crimson Peak too, as others have mentioned. They're not traditional spooky movies, but I also love watching the Del Toro Hellboy movies around this time.