I think overall that all three are fairly liberal schools. If you’re conservative, check the student groups to see if they have Republican or conservative clubs. Vassar usually has one and even had a conservative newspaper back when there were papers at least! But it generally is on the liberal side of things. Skiing in that region is more difficult compared with Hamilton and Middlebury. Vassar is known for being relatively arty (theater is big, creative writing) but it’s sciences are also very strong and it offers greater access to NYC–it’s a 90 minute train ride to the city and you can go for day trips. This is a big deal if you want to see museums, go to plays, hear music, and do internships. Poughkeepsie also has opportunities for real work and internships, and music venues even though the school is located mostly in a suburban area. Academics in all three schools are excellent. Hamilton and Vassar are known for writing. You will graduate knowing how to write well from either institution.