Wintergreen Resort has been voted the best ski resort in Virginia. It has over 1,000 feet of vertical, and over 24 trails. The terrain is 20% easy, 40% more difficult, 40% most diffucult. Wintergreen offers a good deal for first time skiers: a free beginner skiing/snowboard lesson if you rent skis or snowboards with the resort. Rentals are about $33 per day, adult, non-holiday. Ski passes are $42 per day, adult, non-holiday. However, there are discounts for residents of Staunton, Waynesboro, Charlottesville, and neighboring counties on Appreciation Days, when you can get a rental and a day pass for only $32 (it's a great deal! That's why I went with a relative from Charlottesville).
Lift Tickets and rentals can be found at the Skyline Pavilion. There are also a few restaurants in the resort, and many condos. The resort is also open in summer, when you golf or do other activities.