The easiest way to get up to Woodland Park is via a rental car. The COS Airport has multiple rental companies available, but I would make sure to reserve your car prior to arrival as their stock is usually low. If the airport companies are unavailable, there are in-town rental companies that can be accessed via a taxi.

Most people will be staying at the Woodland Country Lodge but the Microtel is directly next door if they fill up. Additionally there are plenty of AirBNBs and Vacation rentals in the area and Colorado Springs is only 30 minutes away for more hotel options.