Jenna Hudson (Bethany Joy Lenz) and Kevin Jenner (Andrew Walker) are polar opposites working for the same online publication in New York City. With both having nowhere they want to be for Christmas, they volunteer for a special writing assignment. After a snowstorm forces their plane to land in none other than Santa Claus, Indiana, the two are placed in a Christmas Wonderland and the focus of their story shifts to saving the historic town inn run by Carol and Christopher Winters. As the two overcome their differences, they also rediscover the magic of Christmas. But with the inn’s fate in jeopardy and the return of someone from Jenna’s past, Carol and Christopher lend a helping hand to bring Jenna and Kevin together.

A curmudgeonly instructor at a New England prep school is forced to remain on campus during Christmas break to babysit the handful of students with nowhere to go. Eventually, he forms an unlikely bond with one of them — a damaged, brainy troublemaker — and with the school’s head cook, who has just lost a son in Vietnam.

When the Lemon Drop Kid accidentally cheats gangster Moose Moran (Fred Clark) out of his track winnings, the Kid promises to repay Moose the money by Christmas. Creating a fake charity for “Apple Annie” Nellie Thursday, the Kid tricks his gang into donning Santa suits and “collecting dough for old dolls” like Nellie who have nowhere to live. Radio personality Marilyn Maxwell assists as the Kid’s girlfriend, while William Frawley and Jay C. Flippen play the lovable, gruff crooks that fall for the Kid’s Santa scam.