42 Holiday Movies to Watch in 2021

The holidays are the best time to cuddle up with a fuzzy blanket, a warm drink (hot chocolate or mulled wine would be perfect), and a cheesy holiday movie. A few new ones came out this year that were great!

I love watching tv shows and movies – I usually always have something on while I’m writing blog posts – and I’m proud to admit I’ve watched 39 out of 42 movies on this list. Yes, some of these are very cheesy, but I made sure to leave off the ones I’ve watched that are actually terrible and a waste of your time.

Because this list is long, I broke it up into three sections: Classics, Romantic Comedies, and Cute & Kid-Friendly.

I hope you find some new holiday movies to watch off this list! :)


Classics

1. Elf (2003)

My all-time favorite Christmas movie! A human raised as an Elf at the North Pole ventures to New York City for the first time in search of his biological father who doesn’t know he exists. There is no holiday movie that brings me more joy and laughter than this one.


2. Home Alone (1990)

Does this one even need a description? Kevin, an 8-year old boy, is accidentally left behind by his family when they leave for a vacation during Christmas. He sets up elaborate booby-traps to protect his house from two burglars trying to break in.


3. Home Alone 2: Lost in New York (1992)

As the title suggests, Kevin gets lost in New York City just a year after the eventful Christmas depicted in the first move. He has cash and credit cards to get him a nice stay at a fancy hotel and deals with the same burglars yet again.


4. The Holiday (2006)

An ultimate classic. Two women (played by Cameron Diaz and Kate Winslet) are having rough times with men and decide to put their houses up on a house-swapping site for a break. They connect and decide to switch houses – one in Los Angeles and the other in England – and unexpectedly fall in love with men they meet in each other’s countries.


5. The Santa Clause (1994)

Scott Calvin’s son Charlie is staying with him for Christmas when he accidentally makes Santa Claus fall off the roof. He then unwillingly becomes Santa Claus due to the “Santa Clause,” a rule that stipulates the person who causes the death of Santa must take over his role.


6. The Santa Clause 2 (2002)

A sequel to the Santa Clause, Scott Calvin has settled into his role as Santa Claus over the last 8 years at the North Pole. He then finds out from his head elf that there’s another clause… the “Mrs. Clause,” which requires him to get married before Christmas Eve. Charlie is now a teenager who has landed himself on the Naughty List. Scott must now search for a wife and help get his son off the Naughty List.


7. The Santa Clause 3: The Escape Clause (2006)

Scott Calvin is now married and expecting a child with his new wife. Jack Frost (Martin Short) makes an appearance as the antagonist and the Council of Legendary figures – Mother Nature, Father Time, the Easter Bunny, the Tooth Fairy, and the Sandman – comes together to talk about his behavior.


8. Last Holiday (2006)

A woman sells everything she owns to live in a fancy hotel in Europe after she is diagnosed with a terminal illness. She withdraws her life savings to live out the short life she has left, but realizes the last thing she needs to complete her life is her crush.


9. Dr. Seuss’ How the Grinch Stole Christmas (1966)

The original Grinch, based on the book by Dr. Seuss, is a cartoon that was never actually in theatres. It was a television release! The Grinch is a grumpy, green, hairy creature who despises Christmas and the joyful, singing Whos in Whoville so much so he steals all their presents before they wake up on Christmas Day.


10. Dr. Seuss’ How the Grinch Stole Christmas (2000)

The live-action version of How the Grinch Stole Christmas features Jim Carrey as the Grinch. It follows the same plot as the original – bitter Grinch hates Christmas and the Whos, steals all their presents on Christmas Eve, and then his heart grows two sizes and all is well again.


11. The Grinch (2018)

Going back to their roots, the newest Grinch movie is animated, but this time in 3D. It also follows the same plot as the previous two films! Dr. Seuss’s widow was the executive producer and actually passed away a few weeks after its release. I really loved this one! 


12. The Polar Express (2004)

Now, this seems to be a really popular movie and has become a classic, but I don’t quite get the allure. The animation is so incredibly life-like compared to other movies at the time – and even compared to movies today! It follows a young boy who wakes up in the middle of the night to a train called the Polar Express that takes kids to the North Pole.


13. Nightmare Before Christmas (1993)

Hot take – this is NOT a Christmas movie! It’s Halloween, but I’m including it because I will also watch it during the holidays. Jack Skellington is the main character and he and his dog zero live in Halloween Town. They discover Christmas Town and Jack tries to bring Christmas to the creepy residents of his town.


14. A Christmas Story (1983)

You’ve probably caught the 24-hour marathon on Christmas Day at some point. This might be the most classic Christmas movie out there! Ralphie is a boy who wants a Red Ryder BB gun for Christmas, despite all the adults in his life telling him he’ll shoot his eye out.


15. Rudolph, The Red-Nosed Reindeer (1964)

This is another movie that was a tv special, but is now aired multiple times during the Christmas season. It’s unique to the other movies so far because it’s stop-motion – produced by Rankin/Bass Productions. Rudolph is a fawn with a glowing red nose that his parents try to hide so he can fit in with the other reindeer. When his real nose is seen, he is ostracized and runs away where he meets up with other misfits.


16. Santa Claus is Comin’ to Town (1970)

Just like Rudolph, The Red-Nosed Reindeer, this movie was produced by Rankin/Bass Productions and is charming stop-motion. It’s based on the song of the same name and is a legend of how Santa Claus came to be.


17. Love Actually (2003)

I think many people hate-watch this movie, but it is still a classic! There are eight couples in the movie whose stories are all followed separately, although they are all slightly connected in one way or another. 


Romantic Comedies


18. Dash and Lily (2020) (series!)

Dash and Lily is the one and only tv series on this list! I had to include it because I loved it so much and thought it was really unique to have a Christmas tv series. It was unfortunately canceled after the first season, but still worth watching! The series revolved around two teenagers in NYC who leave messages for each other in a book at a bookstore, falling for each other before they ever meet in person.


19. The Holiday Calendar (2018)

After her grandfather passed away, Abby inherits an old, antique advent calendar that she soon realizes can predict the future. Abby is working to make it as a photographer, but having a hard time. Her friend Josh, who has just spent time traveling the world as a successful photographer, comes back to see her and reconnect.


20. Holiday in the Wild (2019)

After finding out her husband cheated on her, Kate continues with her plans to go on a safari in Africa where she ends up falling for an elephant conservationist (Rob Lowe). Sure, it’s cheesy, but if you love animals, it’s a pretty touching and fun movie to watch!


21. Holidate (2020)

Sloane and Jackson, two complete strangers, meet while returning presents at the same store. They strike up a conversation and realize both their families are nagging them about being single, so they agree to be each other’s fake dates to their family Christmas parties. You can probably see where this is going… they of course end up falling for each other in the end.


22. The Spirit of Christmas (2015)

A lawyer meets the ghost of a man who previously lived in the old, haunted inn she is trying to get appraised so it can be sold. She must get the ghost to approve of the sale and help him pass to the other side by breaking the curse that keeps him in the old bed and breakfast.


23. Four Christmases (2008)

A couple attempts to spend Christmas with both sets of their divorced parents after their trip to Fiji falls through, forcing them to visit their parents for Christmas instead, and in the process, learn more about each other.


24. Holiday Engagement (2011)

A woman is dumped and doesn’t want to tell her family she is now single during Thanksgiving weekend with them. Instead, she hires a stranger to pretend to be her fiancé and go with her to their holiday weekend


25. Holiday Rush (2019)

A wealthy radio DJ is unexpectedly fired from his job just before Christmas, forcing him and his four spoiled children to move in with his aunt. He works with his aunt and producer to buy another station and keep his show on the air.


26. Last Christmas (2019)

Kate works as an elf in a Christmas store that is open year round and isn’t exactly a great person. She meets a good-hearted man who comes into the shop during the holiday season who seems too good to be true.


27. Happiest Season (2020)

The cutest LGBTQIA+ holiday movie!! A woman is bringing her girlfriend to her family’s house to meet them for the first time over the Christmas holiday. She’s planning to propose, but her family doesn’t even know she is gay or that her girlfriend isn’t just a roommate. When her girlfriend finds out that she’s been kept a secret from her girlfriend’s family, she starts to question their relationship.


28. Love Hard (2021)

I loved this one! Natalie has had a rough time of dating, and even made a career out of it writing about her awful dates for the magazine she works for in LA. When she expands her radius on a dating app, she falls for a guy on the east coast and flies there to surprise him for Christmas, only to discover she’s been catfished.


Cute & Kid-Friendly

29. Klaus (2019)

Jesper is the worst student at the postal academy, and as a result, is sent to a remote island in the Arctic Circle to be the postal man. The town is run down and full of awful, murderous, angry people. Jesper meets a local teacher who is kind and wants to make a difference. He also discovers a lonely carpenter, Klaus, and brings joy back to the town of Smeerensburg.


30. The Knight Before Christmas (2019)

A high school science teacher in Ohio meets a man dressed as a medieval knight and finds out he’s actually time traveled from the past on a quest. She helps him adapt to the modern world and supports him on his quest. Predictably (and adorably), they begin to fall for each other.


31. The Princess Switch (2018)

Vanessa Hudgens plays both main characters in this movie! Stacey owns a bakery with her best friend Kevin, and Margaret is a duchess who’s engaged to the prince of Belgravia. When they bump into each other during a baking competition in Belgravia, they realize how similar they look and decide to switch places for two days. Stacey begins to fall in love with the prince while Margaret begins to fall for Kevin.


32. The Princess Switch: Switched Again (2020)

Two years after the first movie, Margaret inherits the throne to her home country of Montenaro.This movie introduces a third character, duchess Margaret’s bad girl cousin Fiona, who is also played by Vanessa Hudgens. Fiona has spent her family’s fortune and is now a criminal, robbing guests at a royal event. She plans to steal duchess Margaret’s identity so she can be crowned as queen and steal the royal fortune.


33. The Princess Switch 3: Romancing the Star (2021)

Margaret, Stacey, and Fiona come together again to find a sacred relic that was stolen. Fiona brings in her criminal friends to help steal back the relic once they find out who had stolen it in the first place. Things don’t go as planned and they all must switch places with each other to right the situation.


34. Christmas Inheritance (2017)

A rich, spoiled woman is set to inherit her father’s gift business and become CEO. Her father tasks her with a mission to deliver a Christmas card to his ex via bus with only $100 and no credit cards. She becomes stranded at the local inn when a snowstorm comes through the town and without money, she must work at the inn to earn her stay.


35. Jingle Jangle (2020)

An inventor and toymaker’s apprentice steals his best invention, a sentient matador doll, and starts his own toy factory. A few decades later, the toymaker, who was once witty and successful, is now lost and in debt. His granddaughter also has an interest in inventing and visits him at his failing workshop where she helps him get his newest invention to work and sneaks into the former apprentice’s factory to steal back the toymaker’s matador doll.


36. Alien Xmas (2020)

This stop motion movie follows an Alien named X as he attempts to save the world from other extraterrestrials planning to eliminate Earth’s gravity in order to send all the stuff on Earth into orbit. It’s a bit of an odd movie, based on the book Alien Xmas, but it’s still cute! 


37. The Christmas Chronicles (2018)

A brother and sister attempt to stay up and catch Santa on camera on Christmas Eve. The sister, Kate, wakes up to see Santa in her living room and she and her brother Teddy follow him to the roof where they sneak into his sleigh. Kate and Teddy then go on an adventure to help Santa (Kurt Russell) deliver the rest of the presents. 


38. The Christmas Chronicles: Part Two (2020)

Two years since Kate and Teddy climbed into Santa’s sleigh, the brother and sister are now in Cancún with their mom and her new boyfriend. When Kate tries to run away back home to Boston, she is transported to the North Pole by a naughty elf named Belsnickel during the cab ride. She then helps the Claus’s as Belsnickel wreaks havoc at the North Pole.


39. A Christmas Prince (2017)

A young journalist named Amber travels to Aldovia to report on a press conference by Prince Richard, but when she is mistaken as the new tutor for princess Emily, she goes along with it and pretends to be Martha the tutor. Amber falls for Prince Richard and isn’t sure how to tell him the truth about who she is.


40. A Christmas Prince: The Royal Wedding (2018)

Amber and (now King) Richard are engaged and planning their wedding during Christmas time with her father. Their relationship is strained with all the mandatory royal protocols and they hit a few hurdles when they find an economic issue in the country, but in the end they finally have their wedding. 


41. A Christmas Prince: The Royal Baby (2019)

Amber and King Richard are now expecting a baby a year after their wedding and Amber works to get Kings and Queens from multiple countries to sign a peace treaty. They discover the treaty has been stolen and begin investigating to find the culprit and retrieve the treaty.


42. A Boy Called Christmas (2021)

Three children are told the story of a boy who recently lost his mother and lives a poor, underprivileged life with his father. When the king asks the town to venture out and bring back hope in exchange for money, the boy’s father leaves with a group of men in search of a magical place called Elfhelm. The boy, named Nikolas, but called Christmas by his mother, decides to leave on his own expedition in search of Elfhelm with a mouse he kept as a pet. This movie was SO good – I actually cried. 10/10.


Pin it for later

Tap & hold or right-click to save


Kessler

I’m a travel blogger and photographer from the San Francisco Bay Area, splitting my time between there and Santa Barbara. I love to share comprehensive guides about my travels, with a focus on all things sun, sea, and beach! When I’m not exploring new destinations (probably somewhere by the coast), I love being home with my husband and two fluffy kitties, Captain Jack and Sparrow.

https://www.kesslerelsewhere.com
Previous
Previous

A Day Trip to: Sausalito, California

Next
Next

Small Business Gift Guide 2021