This is a list of movie recommendations of movies similar to The Holiday. Bear in mind that this list is in no particular order.
Former music superstar Alex Fletcher (Hugh Grant) used to pack them in back in the 1980s, but now he is reduced to playing nostalgia tours and county fairs. He scores a chance at a major comeback when reigning pop diva Cora Corman (Haley Bennett) asks him to write a song for her, but he hasn’t written anything in years and cannot compose lyrics anyway. Noticing that Sophie (Drew Barrymore), the plant lady, has a way with words, Alex proposes that he and Sophie make beautiful music together.
Everett Stone (Dermot Mulroney) wants to bring his girlfriend, Meredith Morton (Sarah Jessica Parker), to meet his bohemian Connecticut family at Christmas. Straitlaced Meredith, feeling she needs backup, asks her sister Julie (Claire Danes) to come along. Hoping to win the approval of her boyfriend‘s parents Sybil (Diane Keaton) and Kelly (Craig T. Nelson) and the rest of the family, instead, Meredith succeeds only in highlighting her uptight personality and making Everett doubt his intentions.
Irresponsible party girl Maggie (Cameron Diaz) is kicked out of her father’s (Ken Howard) and stepmother’s (Candice Azzara) home, where she lives for free, and is taken in by her hard-working sister, Philadelphia lawyer Rose (Toni Collette). After Maggie’s disruptive ways ruin her sister’s love life, Rose turns her out as well. But when their grandmother, who they never knew existed, comes into their lives, the sisters face some complicated truths about themselves and their family.
The sequel to “Bridget Jones’s Diary” finds Bridget (Renée Zellweger) working as a TV host and still dating barrister Mark (Colin Firth). But Bridget is jealous of the time Mark spends with a co-worker (Jacinda Barrett), and, despite a vacation meant to smooth things over, ends their relationship. On assignment in Thailand, she has a dalliance with her disreputable ex, Daniel (Hugh Grant), and is temporarily jailed on the false accusation of drug smuggling, before Mark comes to the rescue.
Frustrated at his own failures and disillusioned with professional sports, tennis player Peter Colt (Paul Bettany) resolves to retire from competition and become an instructor at an exclusive private club. But when Colt receives a surprise wild-card berth in Wimbledon, he can’t help but enter the tournament. Soon, Colt meets Lizzie Bradbury (Kirsten Dunst), a beautiful American tennis player with an upcoming match of her own, and finds the inspiration he hopes will turn his luck around.
Daphne Wilder (Diane Keaton) is the proud mother of three women: Milly (Mandy Moore), Maggie (Lauren Graham) and Mae (Piper Perabo), and her love for her offspring knows no bounds. Because her youngest, always chooses the wrong man, she decides to take action to prevent Milly from repeating the mistakes of the past. Dating disaster ensues when Daphne tries to achieve her goal by placing an online personal ad for Milly.
Childhood friends Julianne Potter (Julia Roberts) and Michael O’Neal (Dermot Mulroney) had a deal to marry each other if they were still single by age 28. Now, four days before her 28th birthday, O’Neil announces that he’s marrying a gorgeous 20-year-old named Kimberly (Cameron Diaz). Suddenly realizing that she’s actually in love with him, Julianne vows to stop the wedding at all costs. However, when she is appointed maid of honor, things get even more complex.
William Thacker (Hugh Grant) is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott (Julia Roberts) appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.
When aging womanizer Harry Sanborn (Jack Nicholson) and his young girlfriend, Marin (Amanda Peet), arrive at her family’s beach house in the Hamptons, they find that her mother, dramatist Erica Barry (Diane Keaton), also plans to stay for the weekend. Erica is scandalized by the relationship and Harry’s sexist ways. But when Harry has a heart attack, and a doctor (Keanu Reeves) prescribes bed rest at the Barry home, he finds himself falling for Erica — who, for once, may be out of his league
With the wedding of her younger sister (Amy Adams) fast approaching, Kat Ellis (Debra Messing) faces the undesirable prospect of traveling alone to London for the ceremony. While this is bad enough, Jeffrey (Jeremy Sheffield), the man who left her as they moved closer to marriage, happens to be the groom’s best man. Determined to show everyone — most of all Jeffrey — that her romantic life is as full and thrilling as ever, Kat hires a charming male escort (Dermot Mulroney) as her date.