I've been on the Skyway numerous times not in the last 6 years though. There's the possibility of encountering snow at the higher elevations at that time of year, also there are elk and deer in the area, and they start to migrate to lower elevations, so large animals on the road are not too uncommon. About the only place to stay would be in Montrose and Durango, look up the chamber of commerce in each of these cities to look for lodging. If you get to Cortez, there's a Holiday Inn Express that I've stayed at in the past, and has reasonable rates. It's a great ride , and quite colorful if the Aspen trees are turning color.
