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.

Penny is a frazzled wife struggling to keep up with her job, her husband, and her sister's live-in family. While in line to see Santa, she wishes out loud that she had never gotten married. A Christmas Angel grants her wish, but Penny soon realizes what is lacking in her new "single" world and tries to win back the husband and life she had before.