How to Plan a Winter Wonderland Trip to Colorado

How to Plan a Winter Wonderland Trip to Colorado

After my children tore through Christmas in 15 minutes in our family room last year, I was left feeling like I wanted something more meaningful for my family. I vowed to plan a “winter experience” for the following year and having been to Vail before, decided on Christmas in Vail 2021.

If you’d love to wake up to a snowy Christmas morning and would enjoy a horse drawn sleigh ride on Christmas Eve, here are our family’s Colorado holiday travel tips and a few ways to save!



You can chose to fly into Denver or the smaller, Eagle-Vail airport. We have done both. Eagle-Vail (below left) is more convenient but it is also more expensive. At a higher elevation than Denver, it is also subject to more weather issues and more delays. Both times I have flown out of Eagle-Vail, we have been delayed OVERNIGHT in Vail with our entire family … which left us searching for affordable hotels on short notice with no luggage. (On the way home from this trip, we had friends on our flight who got stuck in Denver overnight, with no bags, as their departing flight from smaller Sun Valley was delayed due to weather. They then they missed their connection leaving Denver.)

Denver (above right) is roughly two hours away and far less expensive. There is also more rental car availability here as it is a larger airport. If you choose Denver and are not used to snow, I would recommend flying in during daylight hours so that your drive to Vail is safer. Some roads are steep which may make drivers more nervous in the dark. Denver’s rental car facility is only accessible by shuttle, which isn’t super convenient with a big family. While my husband waited with kids and bags, I went to pick up the car and drove back to pick them up curbside.

Quick Tips:

  • We always rent through Avis. You can sign up for Avis Preferred for free and then just go to your car when you get to the lot. Also, get a car with 4WD.
  • If you have not signed up for CLEAR, I highly recommend it. This is the touchless security system that allows you to bypass long security lines. It uses your eyes or your fingerprint so you can keep your ID and passport in your wallet. It moves super fast and has saved me many times in airports like Denver, Phoenix and Orlando. It’s $179 for the year and only one adult needs it with kids. My husband has it, I have it and then our kids just get in with us. Minors don’t need it which saves time in that TSA doesn’t have to check every kid’s boarding pass.
  • A TSA agent told us we beat the crowds that typically get overwhelming around 9-9:30am. She said that flying out of Denver before 9am is the fastest way to go.
  • On the way out, we used curbside to check us in while my husband returned the car. We tipped an attendant nicely to handle all nine of our bags and we were done in less than 10 minutes.


There are numerous resort towns in the area….Vail, Beaver Creek, Steamboat Springs and Aspen. Our family has continued to return to Vail due to its proximity to family “adventures” and the variety of places to shop and dine within Vail Village and Lionshead. While there are many famed hotels like the Four Seasons, The Arrabelle and The Lodge at Vail, there are also premium hotels like Vail Marriott Mountain Resort and The Grand Hyatt Vail if you have points to spare.

Each time we have been to Vail, we have rented a home or condo via VRBO. For our 2016 Christmas in Vail, we rented a condo within Lionshead, which is a little village in the most popular area of Vail. You could walk to the slopes, shops and restaurants and keep your ski gear right outside the door. This year, we rented a home, five minutes from Vail Village, which was a less expensive option for our big family. We prefer to rent homes if possible due to the size and amenities like fully stocked kitchens and washers/dryers. The downside of renting a home outside of Vail Village is that you always have to drive to ski or shop however, with underground parking garages, we didn’t have any trouble finding a spot. The home we rented is managed by Vacation Rental Collective and owner, Brian, was very helpful when I lost the instructions to get in. (Note - A queen is pictured in master but it is a king now.)

**For timing, both winter Vail vacations we have planned were during the week of Christmas. We didn’t find it overly crowded as many people prefer to be home for the holiday . In contrast, the week after Christmas was very crowded when I went years prior. Many come here for New Year’s Eve so expect a bigger crowd then.


WHAT TO DO in VAIL and the surrounding area

Skiing/Snowboarding - Naturally, the slopes are the big draw to this town. There are ski school adoptions for children beginning at age 4 up through adults.  There is a slope or bunny hill for the rookie to advanced skier.

Adventure Ridge Tubing - This area of Vail Resorts is accessible by gondola at the bottom of the slopes. You take a ride up the mountain to a special area where you’ll find the tubing runs. Children must be 5 and 42” to ride with an adult. Money saving tip: If you ride after 3:30, you do not have to pay for a gondola ticket. (Tickets range from $35-50 for all day access.) The last tube ride time is at 5:00pm so keep that in mind when purchasing a ticket. (Tickets are roughly $80 to tube…but it is worth it! The run is long and the views are worth it.)

Mountain Musher Dog Sledding - This family owned company was one of the highlights of our 2021 trip! We booked three sleds, with mushers, for a 1.5 hour ride though glades of aspen trees. The owners wife makes fresh pumpkin bread and hot chocolate to distribute during the break. The dogs all live on property with the owner and well taken care of. They were friendly to my children and knew their names even within the team. When we left, our faces hurt from smiling and laughing so much!

Sledding - Many rentals have sleds available or you can buy them for $15 from grocery stores. On a day where tubing was closed, we took our kids to Eagle-Vail Golf Club where we spent several hours sledding. The golf course closes in October and then the fairways were filled with families and dogs. There were hills where kids built moguls and we had plenty of room to build snowmen. The best part is what is was free! Here is a great list of sledding hills in the area.

Bearcat Stables Sleigh Riding - We first took a ride on Christmas Even in 2016 and it still remains one of my most cherished holiday memories. Two horses pull a wooden sleigh through the snow and then return you to a historical cabin for a special meal. You can choose to do just do the sleigh ride ($30 per person/kids under 2 free) or do the ride and the dinner where tickets range from $39-89 depending on age.) Food is great and the kids menu had all of the typical favorites ! Book this one early! You can also arrive early to pet horses and roast marshmallows on an open fire. For our family of seven, the entire evening cost $480 which isn’t too bad considering its Vail, on Christmas Eve and included the ride and our meal.)

Ice Skating - There are two places to ice skate in Vail…the Solaris in Vail Square  and the other outside of The Arrabelle, the Alderhoff Ice Rink (more scenic.) Also, in Beaver Creek, less than 20 minutes away, you can skate in their village for $10 and get free cookies at the slopes beginning around 3:00. At the Dobson Arena, there are also ice bumper cars!

Magic of Lights, ice skating shows, snowcats, snowmobiling and other events - Check out Discover Vail for all of the special events and activities during your stay. The calendar comes out in advance so it may help you plan your trip!

Vail Village Shuttle - Take advantage of the Vail Shuttle that runs throughout Vail Village and Lionshead. This is FREE and super convenient. We would ice skate and then hop on the shuttle do go to a different area to shop and eat. We never really looked at the schedule, there were plenty of little stops and we never waited very long. 

SHOP - Shopping amongst Vail’s cobblestone streets and restaurants is incredible. They have plenty of ski shops but also children’s boutiques and brands like Aviator Nation.



Vail Chop House - Located in Lionshead at the base of the slopes, this restaurant has great salads and adult dishes but also a kids menu that features Kraft mac’n’cheese and chicken tenders. 

Blue Moose Pizza - There are a few locations around Vail and Beaver Creek. Casual atmosphere and a few other options for those who don’t want pizza.

Bully Ranch - Known for their burgers and steaks, its also a family favorite due to a kids menu featuring pasta, grilled cheese, chicken tenders, kids steak and smore’s popsicles!

Garfinkles - A cornerstone of Lionshead, Garfinkles has something for everyone! Its a family friendly sports bar grill known for its French Dip sandwich and wings. Like our other recommendations, this also has great kids menu featuring hot dogs, mac’n’cheese and spaghetti.

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