Jay gets a ridiculous amount of snow, but unless you are into skiing woods, there is absolutely no point in being there. The non-gladed trail system is boring. The woods are unparalleled in New England. The nightlife is limited to whatever book you brought with you. I guess you could build a snowman or find a cow to tip over if you felt like it.
The areas in southern Vermont -- Mt. Snow, Okemo, Stratton -- aren't known for being challenging. However, if you're like the vast majority of skiers (i.e., you just like cruising groomers, checking out the views, etc) -- you'll be in heaven at any of those areas. They're all fairly close to each other, so you could base yourself from one and just day trip to the others.
Killington is well, it's Killington. People either love the place or they hate it. The party scene on the Killington Access Road is legendary. There is an endless variety of terrain; whether or not you can find it is another matter. Killington is just down the road from Rutland, which is home to any number of cheapo lodging opportunities.
And that brings us to Stowe and Sugarbush. There are other ski areas in that general vicinity -- Bolton Valley, Mad River Glen, and Smuggler's Notch are all nearby, but Stowe and Sugarbush are the biggies. They get more snow then the southern Vermont areas do, and the terrain is better. They have cruisers, endless bump runs, "classic New England" trails, etc. The towns seem straight ouf of a Norman Rockwell painting; i.e., charming.
For my money, I'd rather be at Stowe then anywhere in Vermont. People always debate as to which is "better" between Sugarbush and Stowe; basically, you can't really go wrong at either.