I like Windham over Hunter. It seems the more serious snowboarders/skiers go to Hunter, but as a beginner-level skier/snowboarder, I find Windham more friendly in this regard. They have more beginner levels (near flat, small incline, and baby slopes, intermediate slopes and then the more advanced slopes) whereas Hunter is like advanced beginner slope and then immediate and advanced slopes).
And their rental snow shoes are more comfortable (which for me, made a huge difference in my ability to ski). And the place has a more family-vibe which makes it more intimate and easy to meet random people when you are there. Hunter feels more corporate for some reason to me.
Optimally, some day I would like to go to Killington or really, Aspen, but maybe when I get better at skiing. I'm also a bigger fan of skiing over snowboarding, the latter which I feel is a bit too dangerous for me. I get no pleasure from surfing on ice. I prefer water. At least with skiing you feel like you are learning something that would enable you to travel great distances in snow, if necessary (unlikely, and not as useful a skill as swimming, per se, but if one ever did have to trek in the snow).
The great thing about Windham is that day trips are easy from Manhattan and utterly affordable. There are buses that go to/from and group packages and lessons to be had so that you can have a full day excursion for under $100, probably even including the cost of food. There are a lot of groups that do this every weekend during the winter season from Manhattan.
That said, the best trips are when you can amass a large group of people you know and rent a cabin. A lot of these ski resorts have lodge cabins and homes with owners willing to rent out for a day or weekend. We did this one year and I think it ended up being like $35/person for a huge three story log cabin with a game room in the basement, huge renovated kitchen and living room with fireplace on the second floor, and themed bedrooms on the third floor. I think there were 5-6 bedrooms total though some people also slept on couches in the living room and cots. There were no issues with heating and good use was made of the facilities. And the views from the cabin were epic. You got to feel like you owned property at a ski resort even if just for a night. read more