娜塔莉的父亲不幸离世，娜塔莉被告知自己成为家里唯一的继承人，而自己玩世不恭的哥哥没有继承父亲的任何遗产。善良的娜塔莉虽然不知道哥哥的下落但决心将自己的一半遗产留给哥哥，以挽留哥哥跟自己经营一个寄宿旅馆。然而贪婪的哥哥闻讯赶来只想骗取娜塔莉的遗产，并没有痛改前非的意思。哥哥为了还债还找来行骗高手装作抢劫犯行骗。天真的娜塔莉信以为真，一心为哥哥抢回遗产，但是残酷的真相让她倍受打击。最后娜塔莉决定给游手好闲的哥哥一次教训，她精心策划了一场骗局让哥哥深感抱歉，同时又成功的抢回了属于自己的遗产。影片最后兄妹俩和好如初，但是向往自由的哥哥最终还是离开了，妹妹把父亲生前最珍爱的珍藏硬币留给了哥哥。

Riley Thomas (Abigail Hawk) is a rising star at one of the world's most noted holding companies. With Christmas fast approaching, she is sent to the small town of Chestnut, Vermont to evaluate the assets of one of their companies, an outerwear clothing manufacturer. As she begins making plans for liquidation, she hires the company's founder, Nick (Howard Hesseman)-now retired-as her apprentice to help. Of course, everyone assumes she's there to save the company and she keeps her true motives a secret. In the process, she comes to appreciate what the company means to the small town; and she falls in love with its youthful CEO, Wyatt (David O'Donnell). She slowly comes to embrace the small town's values and even helps create a new product line just in time for Christmas. As her priorities change and her love grows, will Riley be able to stand up to her boss, Preston Bullock (Chevy Chase) and save the company she was supposed to destroy?