When Abby O'Brien was 17 years old, her mother, Megan, left her father, Mick, Abby and her siblings Bree, Kevin, Connor, and Jess. Sixteen years later, Abby, a successful career woman and divorced mother of twin daughters, Carrie and Caitlyn, lives in New York. Just when Abby is told her ex-husband Wes is getting remarried, her sister Jess asks her and the girls to visit Chesapeake Shores for a weekend. Abby is concerned upon learning Jess is renovating a rundown home into a bed and breakfast and is also needing help with finances. Returning home, Abby sees her high school sweetheart, Trace, now a successful country musician, whom she left to move to New York. Meanwhile, there is tension between Mick and Abby, stemming from him being a frequently absent parent when she was growing up and its negative impact on the family.
Abby O'Brien Winters returns to her hometown of Chesapeake Shores, Maryland, after receiving a panicked phone call from her younger sister Jess, who has renovated the Inn at Eagle Point. Abby's demanding career, divorce and young twin daughters, has kept her busy to even think about the town her father built. Saving her sister's inn from foreclosure means dealing not only with her fractured family but also with Trace Riley, the man she left ten years ago. He initially is an obstacle but becomes an unexpected ally and a second chance at finding love.