Teens Kara Gentry (Sierra McCormick) and Jessie Wilkins (Brighton Sharbino) are in for similar Christmases--and aren't quite looking forward to them. With both girls still grieving the loss of their mothers, Kara and Jessie are both preparing to spend Christmas with their grandparents--this being the first time either girl will have met them. Coincidence has Kara and Jessie seated next to each other on the plane ride to Oklahoma, and after bonding and realizing their shared plans for the holidays, the girls hatch a plan: swap places for Christmas.
Alice Marina (Cindy Busby) is a woman in Minneapolis who comes from a large family and is working to preserve the legacy of the family store by taking over ownership. Jack Totah (Benjamin Hollingsworth) is a travelling businessman from Dublin, Wisconsin whose only family is his uncle Nabeh (Barclay Hope) and who, like Alice, has a love for Christmas. The two strangers find themselves meeting unexpectedly when a misunderstanding leads them to spending a night together at a gala, and when the two realize they're both set to attend the same wedding, another freak occurrence results in the two travelling to the event together.
Having grown up in the small town of Midway, Utah and now running her family's "Mistletoe Diner", Aria Eubanks (Kellie Pickler) has always had a fondness for Christmas. Now, with a ski resort threatening to destroy the small businesses of Midway, Aria is hoping out hope for a miracle to turn things around. Specifically, she's hoping that successful travel writer Sterling Masters (Christopher Russell) will choose Midway as the latest destination to write about for his annual "Big Holiday Adventure" article.
While she may have penned and starred in a big musical on Broadway, Katherine Clark (real-life Broadway star Kristin Chenoweth) has found her true passion in teaching a Christmas youth choir. But as she prepares her students for their annual Christmas Eve fundraiser performance, she finds herself confronted with two major hurdles: the usual writer of their annual original closing song--which is always put up for sale to ensure there are funds for next year's performance--is unavailable, and one of her star vocalists comes down with the flu.
Casey Paulson (Madison McLaughlin) has had it hard the past few years. While she used to be a popular member of the cheerleading squad, a house fire that killed her father and destroyed her hair took everything from her, leaving her as the target of bullying from her former friends Hailey (Ava Allan) and Clair (Ashlee Füss). On top of that, Casey deals with estrangement from her well-meaning but stressed mother Laura (Heather McComb) and verbal abuse from Laura's boyfriend Harlen (Brendan McCarthy).
Violinist Danielle Turner (Helena Mattsson) is a gifted musician who is the latest protege of conductor James Hart (Max Ryan). Despite this opportunity being her potential big break, Danielle can't help but feel guilty about joining James on his music tour--as her departure left her at odds with her sister Heidi (Danielle C. Ryan). Now that she's back in town, Danielle is hoping to use this as her chance to make up with Heidi and rekindle their connection. Danielle is also enjoying a romantic relationship with James, having been swept off her feet by her handsome and charismatic conductor.