Depending on where you live, you might get a chance to see them over Thanksgiving. It's only about three or four days, though.
If you live on the Left Coast, you could always fly to BWI or DCA and get a hotel in Annapolis and pick up your Plebe for the few days.
That way, you maximize the visit and your Plebe doesn't have to travel.
Occaisionally they get something called a "meritorious weekend" in which they have leave that is awarded sort of at the last minute for any number of reasons (the football team wins a game, the Brigade does something worth giving them the weekend, etc.) We went there last fall (I think it was in October) and stayed a week, without any hopes of seeing our DS. Their meritorious weekend happened to be on the second weekend we were there, so that was pretty convenient. We got to take him back to the hotel with us and he was glad to get off The Yard. That was just dumb luck, though.