The story follows a headstrong music manager in desperate need of a hit song for his last remaining client, who finds himself falling for a gifted singer-songwriter with abandoned dreams of making it big, as he attempts to secure the rights to a Christmas song she wrote years ago.

Just three days out from their wedding day, Jess and Max are ready to call it quits from the out-of-control planning. They visit Billie, the owner of a wedding donation company, specializing in donating leftover wedding elements to those in need. However when Max’s brother Charlie will stop at nothing to keep them together, he enlists the help of Billie to ensure this meant-to-be couple gets hitched once and for all.

As Christmas approaches, Paula, a St. Louis antique appraiser, reluctantly accepts a marriage proposal from her boyfriend, Daniel, a career-focused attorney. When her Aunt Jane senses she has mixed emotions over the engagement, she invites Paula to her Nantucket home. Upon her arrival, Paula plans a trip to the nearby island of Martha's Vineyard where she meets a charming inn owner.

Suzie, a rising young architect, returns to her small hometown in Maine for Christmas. When she gets there, she is pushed to follow her grandmother's footsteps and enter the local gingerbread house competition.

Erin is planning the town’s Christmas celebration and must win over firefighter Kevin in order to obtain the beautiful spruce tree from his property for the celebration.