Jack Carter, a man constantly living in a state of regret, takes his technology-obsessed family, including their lovable dog Buster, on a Christmas vacation to the mountains in the hopes of reconnecting with them. While on vacation, Jack and his family run into an estranged, uber-competitive friend of Jack's, who now lives the life of luxury Jack pines for. Through a series of juvenile competitions, Jack realizes that the love of his family is more rewarding than anything money could buy.

After wondering what her life would be without children, workaholic Sharon Holden is unexpectedly granted her wish during a Christmas vacation at her and husband Dustin's old stomping ground at a ski lodge in Utah.