Cozy outdoor courtyard setup with pumpkins and candles for a festive holiday movie night

The holidays bring out the best traditions: warm drinks, twinkling lights, cozy gatherings, peppermint bark, and of course, movies! Whether you’re planning a festive movie marathon, looking for something the whole family can enjoy, or curating the perfect film for a crowd, certain classics stand the test of time.

Below is a list of our favorite holiday movies. Each offers something unique, magical, and worth revisiting year after year. From nostalgic childhood favorites to unexpected action flicks set on Christmas Eve, these films are our go-tos as the snow starts to fall.

  1. The Polar Express (2004)

    Plot Summary: Based on the beloved children’s book, The Polar Express tells the story of a young boy who boards a magical train bound for the North Pole on Christmas Eve. Along the way, he discovers friendship, courage, and the true meaning of belief.

    Best For: Families with young kids, animation lovers, and anyone who enjoys magical, heartwarming storytelling.

    Why It’s a Holiday Favorite: Its stunning animation, immersive soundtrack, and message about believing in the magic of Christmas make it essential holiday viewing.

  2. Die Hard (1988)

    Plot Summary: New York cop John McClane fights off a group of terrorists who take hostages during an office Christmas party. It’s action-packed, fast-paced, and unexpectedly festive, even if the debate about whether it’s a “holiday movie” never ends.

    Best For: Fans of action movies, adults looking for something different from the traditional holiday lineup, and couples who want a more adrenaline-fueled movie night.

    Why It’s a Holiday Favorite: Christmas setting? Check. Holiday party? Check. Redemption, love, and epic one-liners? Absolutely. Die Hard gives the holiday genre an edge.

  3. How the Grinch Stole Christmas (2000)

    Plot Summary: Jim Carrey brings the iconic Dr. Seuss character to life as the Grinch, a grumpy recluse who despises Christmas and devises a plan to steal it from the Whos of Whoville. But his heart grows three sizes when he discovers the holiday spirit.

    Best For: Families, kids, and anyone who loves big costumes, big laughs, and Jim Carrey’s unmatched energy.

    Why It’s a Holiday Favorite: It’s visually stunning, endlessly quotable, and delivers a timeless message about kindness, community, and what Christmas is really about.

  4. Elf (2003)

    Plot Summary: Buddy the Elf travels from the North Pole to New York City to find his biological father, bringing chaotic cheer and a childlike enthusiasm that no one can resist.

    Best For: All ages. Families, friend groups, and anyone who needs a laugh (or a reminder to “spread Christmas cheer by singing loud for all to hear”).

    Why It’s a Holiday Favorite: Will Ferrell’s performance is iconic, the humor hits every time, and the movie strikes the perfect balance between silly and sincere.

  5. The Holiday (2006)

    Plot Summary: Two women, Amanda (Cameron Diaz) and Iris (Kate Winslet) swap homes for Christmas to escape heartbreak. In their new surroundings, they find love, healing, and the charm of living differently.

    Best For: Rom-com lovers, couples, and anyone who wants something soft, comforting, and charming.

    Why It’s a Holiday Favorite: It’s cozy, romantic, beautifully scored, and has become a must-watch for anyone who wants a feel-good December movie.

  6. Love Actually (2003)

    Plot Summary: This ensemble film follows multiple interconnected stories of love, heartbreak, family, and holiday chaos. All this set against the backdrop of London during Christmas. We also get the iconic poster board declaration of love scene.

    Best For: Adults, couples, and fans of British humor and ensemble storytelling.

    Why It’s a Holiday Favorite: It captures the messy, complicated, and wonderful parts of love while giving you a dozen memorable moments (and even more quotable lines).

  7. Home Alone (1990)

    Plot Summary: Eight-year-old Kevin McCallister is accidentally left behind when his family flies to Paris for Christmas. He ends up defending the house against two bumbling burglars in what might be the most creative home-defense sequence in movie history.

    Best For: Families, nostalgia lovers, and anyone who wants big laughs and heartwarming moments.

    Why It’s a Holiday Favorite: It’s endlessly rewatchable, genuinely funny, and still gives audiences that warm “family matters most” message at the end.

  8. The Nightmare Before Christmas (1993)

    Plot Summary: Jack Skellington, the Pumpkin King of Halloween Town, discovers Christmas Town and decides to take over the holiday with chaotic but charming results. We also have a fascinating side plot of Sally trying to grow into her own and escape her overbearing father.

    Best For: Fans of Tim Burton, stop-motion animation, alternative holiday vibes, and those who like both Halloween and Christmas.

    Why It’s a Holiday Favorite: It’s visually iconic, musically unforgettable, and appeals to audiences who like their holiday movies with a twist.

  9. The Santa Clause (1994)

    Plot Summary: After accidentally causing Santa to fall from his roof, Scott Calvin (Tim Allen) unknowingly becomes the next Santa Claus. He slowly transforms physically and emotionally into the role over the course of the season.

    Best For: Families, Tim Allen fans, and anyone who loves classic ’90s holiday charm.

    Why It’s a Holiday Favorite: It’s funny, magical, and features one of the most memorable Santa transformations in movie history.

  10. Just Friends (2005)

    Plot Summary: Chris Brander (Ryan Reynolds) returns to his hometown during the holidays and reconnects with his high school crush while navigating hilarious chaos, misunderstandings, and over-the-top holiday antics. We also love Anna Ferris’ over the top celebrity behavior.

    Best For: Adults, comedy lovers, and fans of Ryan Reynolds’ signature humor.

    Why It’s a Holiday Favorite: It’s light, funny, and filled with small-town holiday nostalgia, the perfect comfort rewatch.

Holiday movies aren’t just entertainment, they're tradition. They bring people together, spark meaningful memories, and create the perfect backdrop for cozy winter nights. Whether you’re watching with family, hosting a festive gathering, or just enjoying a quiet evening in, these films add warmth and magic to the season.


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Bring the warmth, comfort, and wonder of these holiday classics outdoors with Courtyard Experiences. From the screen and sound to cozy seating, we handle everything so you can focus on the memories. Book your holiday movie gathering and make it truly unforgettable!

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