The 15 Best Holiday Movies to Watch This Season

Must watch movies this holiday

The holiday season is hands-down the best time of the year to watch movies. Who doesn’t love snuggling under a blanket in front of the TV? Add cookies and a hot drink, a fire in the fireplace, snow falling outside, and a Christmas tree within eyesight… you’ve got yourself the perfect situation for watching holiday movies!

Some of the best holiday movies are obvious (like “White Christmas”), while others aren’t quite as holiday-related, yet somehow still seem fitting to watch this time of year. Who doesn’t love watching the “Jingle Bell’ dance in Mean Girls, or the sentimental scene in “You’ve Got Mail” when Kathleen Kelly decorates a Christmas tree and waxes poetic about Joni Mitchell?

So, go ahead, pop in a movie! Watch one a day from Thanksgiving until the New Year, we’ll never tell!

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It's a Wonderful Life

It’s A Wonderful Life (1946)

An angel is sent from Heaven to help a desperately frustrated businessman by showing him what life would have been like if he had never existed. A heartwarming movie that will bring tears to your eyes every year.

Cast: James Stewart, Donna Reed, Lionel Barrymore, Thomas Mitchell, Henry Travers, Beulah Bondi

Will Ferrell in Elf

Elf (2003)

Raised as an oversized elf, Buddy travels from the North Pole to New York City to meet his biological father, Walter Hobbs, who doesn’t know he exists and is in desperate need of some Christmas spirit. A quirky holiday classic that will always have you laughing.

Cast: Will Ferrell, Bob Newhart, Mary Steenburgen, Zooey Deschanel, Peter Dinklage

The Family Stone (2005)

Everett Stone wants to bring his girlfriend to meet his Connecticut family at Christmas. Straitlaced Meredith, feeling she needs backup, asks her sister Julie to come along. Hoping to win the approval of her boyfriend’s parents and the rest of the family. But Meredith succeeds only in highlighting her uptight personality and making Everett doubt his intentions. This movie will have you laughing and crying all at the same time, have your tissues ready!

Cast: Dermot Mulroney, Sarah Jessica Parker, Diane Keaton, Luke Wilson, Claire Danes, Rachel McAdams, Craig T. Nelson, Tyrone Giordano

the holiday christmas movie

The Holiday (2006)

Two women troubled with guy-problems swap homes in each other’s countries, where they each meet a local guy and fall in love.

Cast: Cameron Diaz, Kate Winslet, Jude Law, Jack Black, Eli Wallach

Holiday Inn Movie

Holiday Inn (1942)

At an inn which is open only on holidays, a crooner and a hoofer vie for the affections of a beautiful up-and-coming performer. A classic like this never fails to put you in the holiday spirit.

Cast: Bing Crosby, Fred Astaire, Marjorie Reynolds, Virginia Dale

Love actually movie

Love Actually (2003)

Full of an all star cast, this movie follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England. All the feels….

Cast: Hugh Grant, Liam Neeson, Colin Firth, Laura Linney, Emma Thompson, Alan Rickman, Keira Knightley, Emma Thompson, Martine McCutcheon, Bill Nighy, Gregor Fisher, Thomas Brodie-Sangster

White Christmas (1954)

A successful song-and-dance team become romantically involved with a sister act and team up to save the failing Vermont inn of their former commanding general. The talent in this moving will have you in awe.

Cast: Bing Crosby, Danny Kaye, Rosemary Clooney, Vera-Ellen, Dean Jagger

last holiday

Last Holiday (2006)

The discovery that she has a terminal illness prompts introverted saleswoman Georgia Byrd to reflect on her overly cautious life. So, Georgia withdraws her life savings and jets off to the Czech Republic where she lives like a millionaire.

Cast: Queen Latifah, LL Cool J, Timothy Hutton

Mean Girls Movie

Mean Girls (2004)

Cady Heron is a hit with The Plastics, the A-list girl clique at her new school, until she makes the mistake of falling for Aaron Samuels, the ex-boyfriend of alpha Plastic Regina George. It’s so fetch.

Cast: Lindsay Lohan, Rachel McAdams, Lacey Chabert, Amanda Seyfried, Amy Poehler, Tina Fey

You’ve Got Mail (1998)

Book superstore magnate, Joe Fox and independent book shop owner, Kathleen Kelly fall in love in the anonymity of the Internet both blissfully unaware that he’s trying to put her out of business.

Cast: Tom Hanks, Meg Ryan

The Holidate

The Holidate (2020)

Fed up with being single on holidays, two strangers agree to be each other’s platonic plus-ones all year long, only to catch real feelings along the way. The comedy it top-notch while still giving you the holiday romance cringe.

Cast: Emma Roberts, Luke Bracey, Kristin Chenoweth, Manish Dayal

A Christmas Story Original

A Christmas Story (1983)

In the 1940s, a young boy named Ralphie Parker attempts to convince his parents, teacher, and Santa Claus that a Red Ryder Range 200 Shot BB gun really is the perfect Christmas gift. From the setting to the acting, everything about this movie is fun and nostalgic.

Cast: Peter Billingsley, Darren McGavin, Melinda Dillon, Ian Petrella, Jean Shepherd

Rudolph Claymation

Rudolph the Red-Nosed Reindeer (1964)

This classic clamation holiday movie follows a young reindeer named Rudolph who lives in the North Pole. His father is one of Santa’s reindeer so it’s expected that Rudolph will be one too. However, his one unique feature causes him to be ostracized: his red nose.

Cast: Billie Mae Richards, Burl Ives, Stan Francis, Paul Soles

The Princess Switch (2018)

Competing in a Christmas baking competition in Belgravia, a Chicago baker bumps into the prince’s fiancée–who looks just like her. They switch lives for two days. Get your holiday romance movies in while you can!

Cast: Vanessa Hudgens, Sam Palladio, Nick Sagar

Klaus netflix original movie

Klaus (2019)

A simple act of kindness always sparks another, even in a frozen, faraway place. When Smeerensburg’s new postman, Jesper, befriends toymaker Klaus, their gifts melt an age-old feud and deliver a sleigh full of holiday traditions. This Netflix movie includes a star-studded cast and will have you laughing, feeling, and rich with Christmas spirit.

Cast: Jason Schwartzman, J.K. Simmons, Rashida Jones, Joan Cusack, Will Sasso, Norm MacDonald

What are your favorite films to watch over the holidays? We’d love to know, comment below!

best holiday movies
Laura Rennie
Laura Rennie
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Laura Rennie is a freelance writer and currently serves as the editorial manager for Maryland Road Trips. She loves reading memoirs, cooking curries and exploring new places. Her most unique travel experiences include sledding in the Alps, getting engaged in London and being stared at in a Korean spa in Seoul.

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