Cheap plane tickets around the holidays..any help?

My SO just left from our first real visit as a couple, and I'm still in that weepy-stay-in-bed-all-day phase, so I'm trying to be productive and think ahead to our next possible visit, around the December holiday, during our winter breaks. I'm finding that I don't really know anything about shopping for plane tickets, so I'm really hoping that you guys can help me out! I've been using Kayak to look for tickets, I've seen some users rave about it.

Currently, for a round trip from MD departing in late December, and returning from OH in early January, it's about $269 via Southwest for a direct flight with no stops, which, to be honest, makes the most sense to me considering it's only about an hour long flight. Also, I'd prefer a direct flight, especially because it'll be during the winter and there might already be some delays because OH gets some intense winters.

Now, is that considered a "good" price? I really have no concept of this, help me out! And what are some tips for shopping for plane tickets during this time? I know that it's considered peak time, so I won't be getting a fabulous deal or anything, but I'd like to not overpay too much. Thanks so much!