I taught skiing in the Banff and Jasper areas for a number of years until I had to maintain a real job.
Some of the folks here have mentioned Whistler and it's great if you can swing the money. The Banff area has sunshine Village, Lake Louise and Norquay, all close to town.
The resorts on Colorado are absolutely wonderful and I can't recommend Vail and Winter Park more highly.
There are a few questions to consider:
1) Where's the snow? Conditions are spotty in some places and I'd advise careful research if I were you.
2) Where are the deals? Package deals can be had which include food and lodging. Check message boards for feedback on any resort you pick.
3) What kind of skier am I ? Some areas have tons of expert terrain, but if you're not a real experienced skier, fear is not a great way to improve your technique. I've seen plenty of people spend considerable money and spend a day in terror just trying to get down the mountain. (Just research KT22 at Sun Valley and you'll know what I mean) Consider taking a private lesson at the resort as it will give you some time to get familiar with the mountain, improve your technique, and you won't have to wait in lift lines during the lesson.
4) What kind of expereince do you want? If you want to ski until you're exhausted, then a place like Whistler might be up your alley. If you want to party, then there are plenty of deals and watering holes to be had at many of the American resorts. If you're travelling with friends, ask yourself if you're going to be skiing with them. If one or more members of the group are struggling to keep up, then consider the area you pick. There are plenty of areas with wide, relatively easy runs that cute little snow bunnies like to inhabit. Bottom line is to make it fun.
