Brooke (Julianna Guill), a young marketing executive, goes back to her hometown excited to relive her Christmas memories, while helping a struggling family-owned winery. Her marketing assignment involves an unlikely partnership with Tyler (Jon Corr), the charismatic, yet stubborn owner of the winery. Brooke quickly learns that the town’s Christmas spirit has disappeared due to a wine conglomerate buying out all of the local wineries. Determined to bring Christmas back to the town, Brooke and Tyler work together and discover they share more than a love for wine.

A big-city sommelier, Camila returns to her hometown and family-run business for the annual ice wine harvest that coincides with the holidays. But the visit is upended when the owner of the vineyard—her beloved godfather—announces they’ve hired a consultant named Declan Monroe to oversee the switch from old world methods to modern technology.

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.