Flight
DIA is a hub for United, Southwest, and Frontier. We would recommend booking one of these for the most flight options.
Rental Car
This is our recommendation for a rental car company, Kris uses them a lot for work. We do recommend renting a car as Winter Park is about an hour and half drive over Berthoud Pass from Denver.
Travel Note
Included is a sitter service located in Grand County. They have been around since 2012 and have great reviews. Here is their Facebook Page: https://www.facebook.com/sitterservicegc/
House Or Rental
There's a good inventory of short term rentals in Winter Park on Airbnb that are relatively affordable.
Hotel
Trailhead Inn is a great local Hotel option, they have rates starting at $99/night (based on availability) visit their website above or call directly. While we do not have a block set-up under our name, we would recommend staying here because of it's great location.