Jack Carter, a modest, middle-aged bakery owner, thinks he and his family are in a rut. Not only can he not provide them with the finer things, he realizes that he's not as close to his kids as he wants to be. His 17-year-old son Kyle is preoccupied with sports and will be leaving for college soon; his 14-year-old daughter Sienna is always lost in her phone. So for the upcoming Christmas holiday, Jack has the brilliant idea to reconnect with his family while also trying to spark his desired writing career by going on a Christmas vacation to a cabin resort in the mountains with no technological distractions whatsoever and make their trip the very best Christmas vacation ever. But the trip seems doomed from the start: their cabin is a dilapidated disaster, the kids are constantly complaining, and then Jack runs into his estranged, uber-competitive friend Robert, who used to vacation at the resort with Jack when they were kids. Robert is rich, successful, and better than Jack at everything. And while Jack and his family stay in a cold, run-down cabin, Robert and his family stay in one of the resort's fanciest newly-renovated cabins. Robert seems to upstage Jack at every turn, and Jack's family appears to be entranced by Robert and his wealth, leaving Jack to feel like a failure. Jack plans to one-up Robert at the very games Robert used to beat him at: the Farthering Pines Winter Olympics, a series of events that Jack's dad invented. But Jack's plan backfires and Robert beats him yet again. Jack has had it. His emotions get the best of him and he apologizes to his family for letting them down as a provider, but they reveal that they think they have the best father or husband anyone could want. Jack finally realizes that the love of his family is more rewarding than anything money could buy.