The answer to this question is simple: if you want to ski at Aspen Snowmass, you should start planning your trip as far ahead as possible. The farther in advance that you plan your trip, the better deals you are going to find. It's not uncommon for the best and cheapest hotels in Aspen and Snowmass to sell out a year in advance. If you want to find the perfect accommodations for your budget, your wants, and your needs, you should be prepared to book far ahead of your intended trip date. However, if your budget is bigger, you can often find hotels in Aspen closer to your trip date, too. Keep in mind, though, that even some of the most expensive properties in Aspen and Snowmass sell out months ahead of time during the peak ski season.