My kid toured Kenyon, which is nearby for us. He applied and was waitlisted. Got in to Vassar and is there now. In the meantime, my spouse and I have been back to Kenyon a couple of times for cultural events. So here are my thoughts:
They’re both super nice colleges, and really both are a little isolated for different reasons, but obviously being able to get to NYC easily is a whole different thing to being near Columbus.
Kenyon is whiter and the students are generally very well-off, as Kenyon does not have the luxury of a large endowment to allow them to pursue applicants from underserved backgrounds. Vassar is, for an elite institution, doing pretty well for diversity. There are plenty of very well-off kids there too, but also a lot of kids from pretty poor backgrounds as well. Middle class kids are a bit of a rarity, is my sense.
Both Kenyon and Vassar are taking steps to improve their strengths in the STEM disciplines. You can get a great education at either college, for sure.
Both schools have serious issues with substance abuse, as do probably all elite LACs. I was a little surprised by the number of ambulance rides out of Vassar. And I seem to recall a Kenyon kid died of alcohol poisoning a while back. My sense (being an elite LAC grad myself) is that elite LACs attract a lot of smart, shy kids who are looking to break out of their shell, like yours, and who unfortunately make their mistakes with drugs and alcohol freshman year of college, instead of in high school.
For our son, Vassar is a much better fit culturally.