Aspen, where the beer flows like wine...
1. Not really. Look for the Aspen Classic Pass. Might be your best bet. Otherwise get a multi day pass.
2. Again, Not really. Especially around Aspen. There are a few Motel type places in the town of Aspen that will be a bit less, but it's pricey. Do find a better deal you are going to have to go down valley. Look at Carbondale, Basalt, Glennwood Springs.