The following version of this book was used to create the guide: Hilderbrand, Elin. The Five-Star Weekend. Little, Brown and Company: 2023.

Hollis Shaw argued with her husband, Matthew, just before he died in a car crash. Her daughter, Caroline, despises her for prioritizing her website—Hungry with Hollis—over her family. Hollis decides to host a Five-Star Weekend at her house on Nantucket and invite four friends, along with Caroline, who will document the whole thing. Tatum is her childhood best friend, who is awaiting a cancer diagnosis. Dru-Ann is her college best friend. She is suffering from a recent scandal at her job as a sports talk show host. Brooke is Hollis' friend from when their kids were growing up. She hates her husband, Charlie, who is being sued for sexually assaulting his colleague. Gigi is Hollis' online friend, whom she met through her website. Hollis has no idea Gigi and Matthew had an affair.

When Caroline arrives on Nantucket, she is secretly fleeing a messy affair with her boss. She runs into Dylan, Tatum’s son and her childhood crush. Dylan kindly offers her a ride home and continues to take her out during her stay despite his ex’s jealousy.

Hollis greets her guests with various degrees of excitement. She is shocked when Jack—her first boyfriend—drops Tatum off. It is clear that Jack still has feelings for Hollis. Caroline is cold and rude to her mother that night.

The women bond that night at dinner, then again the next day while shopping. Hollis gets lunch with Tatum and her husband, Kyle, as well as Jack. They reminisce on their youth together and contemplate Tatum’s pending cancer diagnosis.

Brooke’s husband, Charlie, shows up uninvited to Hollis’ home that night to beg Brooke to forgive him. The women fend Charlie off and are kinder to Brooke after that. Caroline interviews Tatum to ask about her friendship with Hollis. She learns Tatum was hurt and jealous when Hollis left for college and never came back to Nantucket. Caroline learns from Dru-Ann that Hollis lied about having a living mother when they first met. This deception made Dru-Ann question their friendship, but she quickly forgave Hollis.

At dinner in town, a woman named Electra approaches Hollis’ group to say she recognizes Gigi. Gigi panics, afraid Hollis will discover the truth behind her relationship with Matthew. Hollis goes out that night with Tatum, Kyle, and Jack again. She and Jack kiss in the woods afterwards and discuss their relationship. Dru-Ann takes Brooke dancing. Brooke kisses her on the mouth afterwards.

Caroline interviews Brooke, who describes how Electra ousted her from the Mom group she and Hollis were a part of. Hollis did not stick up for her straightaway but took Brooke’s side eventually. Brooke realizes that her suppressed homosexuality made her insecure and thus annoying.

On Sunday, the women head to a boat together. Electra interrupts them on the way and says she remembers seeing Gigi with Matthew. Hollis and Gigi leave the group. Tatum and Dru-Ann discuss their animosity on the boat and forgive one another for the insults they have dealt over the years. Meanwhile, Hollis confronts Gigi back at the house. Gigi tells her about the affair and that Matthew broke up with her on the phone right before he died. He was driving back to Hollis’ house to make things work with her. Hollis decides to forgive Gigi and tells no one of her deception. After the rest of the guests leave on Monday morning, Tatum remains to call her doctor. It turns out she does not have cancer. The women rejoice as Hollis declares her intention to remain on Nantucket.

One year later, Hollis and Jack are dating. They go on a cruise in Italy with Dru-Ann, Brooke, Tatum, and all their partners. On their flight back, Gigi happens to be their pilot. Hollis agrees to say hello to her, feeling happy by Jack’s side.