Winchester doesn't have too much of a night life. They have 3 bars that attract the 20something crowd but are still pretty small. I went to two of them while I was up there and they seemed to have a good atmosphere and one has a DJ on Fridays and live music on Saturdays. I was talking to a P1 and she said that there is a Metro station nearby and they go into DC occasionally. I think it'll be a big change for those of us coming from big cities but hey, at least we'll get a lot of studying done!
For those that have decided on attending Shenandoah, another incoming student and I will be visiting Winchester to look at housing in the next few weeks. We are looking for another 1-2 roommates to share a house. I checked out Stuart Hill and Pemberton Apartments and it just seems that we would get more for our money by renting a house. If you are interested in renting with us, please let me know and I can send you what we will be looking at.