KENDRA JACKSON is a single, high-powered New York attorney, whose firm represents an environmental activist group seeking to halt the removal of twenty-five thousand acres of trees. When a colleague convinces her to take a well-needed break, she books a luxurious spa-hotel in beautiful Chestnut, Vermont for the Christmas holiday.
Upon arrival, she is shocked to find the spa closed for renovations, then stumbles upon a B&B not far away—the epitome of a charming, remote Christmas cottage. She is greeted by the sweetest elderly couple who, after welcoming her to stay on for the week, announce that they are just about to leave for the holidays, so she has the place to herself.
Later that evening, NICK REED, a widower, and his son WILL unexpectedly arrive and confusion sets in. They amicably agree to cohabitate for the week. As Nick and Kendra get to know each other, they find themselves on the verge of falling in love, but Kendra soon puts two and two together and realizes that Nick is the man her law firm is suing! Stuck in this predicament, how long can she keep her true identity from him?
Kendra also attracts the attention of the slick and somewhat slimy ERIC ANDERSON, who casually reveals he is the head of the the group filing the lawsuit.
Later, CARL HARRIS, a partner in the firm, worries that if Kendra gets mixed up with the locals, she may compromise the suit. He books the next flight to Chestnut Hill.
Kendra pays a visit to Chestnut Technologies and Lumber Distribution, the company intending to cut down the trees. Shocked to find each other there, Nick divulges he is the owner and figures out that Kendra represents the firm filing the suit against him. Nick takes her to see the beautiful forest in the Vermont landscape where the targeted trees grow, and finally explains all: He plans to remove them in order to repopulate the land with chestnut trees, for which the area had been revered for its ecological benefits, and which had all but disappeared a century ago from disease. The trees cut down will be donated to schools, municipal parks, and charitable organizations.
Christmas Eve arrives with Nick and Kendra, lanterns in hand, attending a traditional lantern festivity, when Carl at last catches up to them and confronts Kendra with his accusations of ruining the case. With her newfound evidence, she decides she cannot continue with the lawsuit. Carl tells her she is fired, but it’s too late. Not only did Kendra already give her resignation in the previous hour, she will now be representing Nick and his company.
Carl is defeated, knowing he is no match for her and storms off. A huge burden lifted, Kendra and Nick join the community at the church for Christmas celebrations.
On Christmas morning, Nick, Kendra and Will awaken to a winter wonderland, as well as to their wonderful future together. And who are the owners of the cottage?
Kendra shows Nick a picture on the wall of the old couple. Nick is dumbfounded—they are his parents, ten years deceased. The mystery fades as Will calls them outside to witness the crowning of his snowman, as snow falls on Chestnut Cottage.