My family and I (wife, now 17 yr old son, 8 yr old girl) have enjoyed spending a couple of Christmases in the Woodland Park/Cripple Creek area. My wife (from Brazil, NO pics) has always wanted to spend a "Christmas with snow in the mountains". Something that doesn't happen much in East Texas. So, a few years ago we got an Airbnb in the middle of nowhere (address said Cripple Creek). It was really magical. Just us four in a small cabin with as much snow as we could ever want. We could see Pike's Peak in the distance and spent a lot of time playing games, watching movies, and playing in the snow.
On our first trip about 4 years ago, we drove to Colorado Springs to go ice skating and some shopping. We also went to Santa's North Pole Amusement Park (about a 35-40 min drive from where we were) at the base of Pike's Peak two days before Christmas. It was a fun little amusement park with great views and is home to the "highest elevated ferris wheel in the US". Uh, we rode it and I was not a fan. Looked like I was going to fall off the side of the mountain. We spent Christmas Eve/Day enjoying the peace and quiet and a nice fire .
We went back two years ago and took my in-laws with us. We stayed in a different place not too far from where we originally stayed a couple years before. This trip we spent some more time in Colorado Springs, visited the Garden of the Gods, and drove to Breckenridge to check out the town and do some tubing. It was a blast. I WILL SAY: If you go during the Winter, drive a vehicle with AWD or 4x4. We drove a front-wheel drive minivan (to fit everyone) and had to use chains several times, including driving through Hoosier Pass. It was hectic.
If we go to this area again, which I hope to do, we will look at finding a place in Woodland Park, west of Colorado Springs. Not as secluded as what we did before, but definitely more convenient. While we did drive through Cripple Creek on both visits, we did not do any gambling.