Movies like Christmas on Windmill Way (2023)
The best movies like Christmas on Windmill Way (2023) are Jingle Around the Clock (2018), Never Kiss a Man in a Christmas Sweater (2020) and 12 Gifts of Christmas (2015). If Christmas on Windmill Way hooked you with its romance and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Apartment (1960)8.2/10 from 2,848 votes
- NewestF Valentine's Day (2026)Released 2026
Jingle Around the Clock (2018)
Elle decides to reunite her college friends for Christmas, but her plans are thwarted by an opportunity at work to spearhead a Christmas campaign relaunch. She's forced to team up with ad campaign "fixer" Max, who has a completely different take on the holidays. As the two work together, they find themselves falling for each other. With the help of a little Christmas magic, will Elle pull off the perfect Christmas reunion and find the love she’s been searching for?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisNever Kiss a Man in a Christmas Sweater (2020)
Single mom Maggie is facing Christmas alone until Lucas crashes into her life and becomes an unexpected house guest. Together they overcome Christmas while finding comfort in their growing bond.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like this12 Gifts of Christmas (2015)
When Anna Parisi, an unemployed fine arts painter, is unable to make ends meet, she is hired to become a personal Christmas shopper for Marc, an uptight corporate exec. As they begin working together, Marc learns that Christmas giving has less to do with the amount of money spent and more to do with the importance of the gift, while Anna discovers she might find success as an artist in a way she never expected. The best gift of all of course is the love they discover with one another.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like this'Twas the Text Before Christmas (2023)
Addie is a New York City chiropractor mistakenly receives a text from “Nana.” The accidental text turns into a loving friendship between the matronly Nana and Addie who now communicate regularly. Nana invites Addie to spend the holiday in Vermont. It is picture-postcard perfect and exactly as Nana described except for one surprise. Nana’s single son, James, a traveling doctor is also home for the holidays. Over three consecutive years, James and Addie are together during the holidays, though it isn’t until they are both single that they begin to see each other in a different light.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisA Merry Christmas Wish (2022)
Janie, a rising marketing executive living in The Big Apple, returns to her hometown of Woodland Falls when her Great-Uncle Randall passes away. Randall has even arranged for his farmhand, Dylan to help at the event, which is being held in the farm’s sprawling barn. Aware that her Manhattan boyfriend is anxious for her to return to the city so the pair can jet off to a previously planned holiday on the beach, Janie begins to feel an unexpected emotional tug about living life in a more authentic, meaningful way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisThe Mistle-Tones (2012)
Holly, blessed with an amazing singing voice, is all set to audition for the newly vacated spot in a legendary local Christmas group which was founded by her late mother years ago. Shocked and upset when the slot goes to the barely talented best friend of the group's leader, Marci, Holly sets out to create her own musical group, The Mistle-Tones. After challenging their rivals to a sing-off on Christmas Eve, Holly finds herself on a journey to the real meaning of Christmas with some new friends and a new love thrown in for good measure.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Christmas Miracle for Daisy (2021)
Whitney Alder owns interior design firm Marietta Designs, which she runs with her friend Andi in the small town of Marietta, Montana. Whitney is designing Santa’s float for the annual Marietta Christmas Parade when a potential job opportunity comes her way: the full redesign of a landmark home by Christmas Eve.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisChristmas in Evergreen: Letters to Santa (2018)
Lisa's trip home to Evergreen for the holidays finds her shepherding an effort to save the town's beloved general store, fulfilling the wishes of a Christmas past and finding a romance full of Christmas magic.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisMerry Christmas, Drake & Josh (2008)
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisPoinsettias for Christmas (2018)
It’s just weeks before Christmas when Ellie gets a call to return home to help her father on the family’s poinsettia farm. The family business is on the line to deliver tens of thousands of plants for the town’s annual parade. The problem is — the poinsettias have yet to turn red! As Ellie searches for the solution, she is reminded of where her heart truly lies as she falls in love with both her roots and a local botanist.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas at Grand Valley (2018)
Burned out from the hubbub of the Chicago gallery world, artist Kelly returns home to the picturesque Grand Valley just in time for Christmas. Leo, businessman and all-star dad to his children, struggles to balance his time this holiday season. When he is assigned to review a hotel in Grand Valley for its value, he sees this as the perfect opportunity for a Christmas family vacation. It isn’t long until Kelly and Leo’s worlds collide.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Christmas Prince: The Royal Baby (2019)
Christmas brings the ultimate gift to Aldovia: a royal baby. But first, Queen Amber must help her family and kingdom by finding a missing peace treaty.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas Next Door (2017)
Eric Randall, an author of bachelor lifestyle books, is left in charge of his young niece and nephew for the holidays. Eric turns to his neighbor April, a lover of all things Christmas, for help.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisKristin's Christmas Past (2013)
Kristin, a cynical 34-year-old, drinks a mysterious champagne on Christmas Eve and wakes up seventeen years in the past, sharing a room with her 17-year-old self. Given the chance to change the worst Christmas of her life, she attempts to fix past mistakes, only to discover surprising truths about her family that may help her mend her present-day relationships.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisA Glenbrooke Christmas (2020)
As Christmas nears, heiress Jessica Morgan seizes what seems like her last chance to experience a relaxed Christmas and heads off to the small town of Glenbrooke, where she meets a handsome fireman.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisMarry Me at Christmas (2017)
Organizing a Christmas wedding is a true treat for bridal boutique owner Madeline Krug. She loves the challenge of finding the perfect dress for the bride and orchestrating an exquisite event. What Madeline didn’t expect was to be swept off her feet by the bride’s gorgeous brother, movie star, Jonny Blaze. Jonny came to the quirky town of Fool’s Gold to support his sister -- not to fall in love. Yet Madeline is the most extraordinary woman he’s ever met, and she finds the real Jonny even more captivating than her celebrity crush. Will the action star be brave enough to take on the role of a lifetime?
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas on Honeysuckle Lane (2018)
Emma Reynolds returns to Oliver's Well to celebrate Christmas for the last time with her siblings in the home they grew up in. After their parents recently passed, the siblings reluctantly agree to sell the family home on Honeysuckle Lane after the New Year, leaving Emma in charge of its belongings. While antiques expert Morgan Shelby appraises Emma's mother's collection, they find a hidden surprise in an antique desk that takes them on a journey to discover the power of love and family during the holidays.
Why it matches: Recommended by TMDB viewers · both romance
SnoozefestMovies like thisSharing Christmas (2017)
A real estate developer is given the opportunity of his career to transform an old shopping complex into a prime location. Unfortunately, there is one tenant who is holding out—the Christmas shop owner he met by happenstance just days ago.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisDolly Parton's Christmas on the Square (2020)
A rich and nasty woman returns to her hometown to evict everyone but discovers the true meaning of Christmas thanks to the local townsfolk – and an actual angel. Features 14 original songs with music and lyrics by Dolly Parton!
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisMy Christmas Inn (2018)
With the holiday season in full swing, Jen Taylor is about to score a big promotion at the San Francisco ad agency where she works. But her life is unexpectedly turned upside down when she inherits a cozy inn in Alaska from her aunt. When she goes to inspect the property and meets handsome town attorney Steve Anderson, she's surprised to find that nothing is what she expected. The small town community is full of fun and festive Christmas traditions and soon, Jen starts wondering if the inn might just be the place she belongs, and if Steve could be the Mr. Right she has been waiting for.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisAll I Didn't Want for Christmas (2022)
Emily Harris is not doing great. In a desperate attempt to improve her life and make this Christmas not totally suck, Emily writes a letter to Santa. Fortunately, and unfortunately, her wine-soaked wishes start coming true.
Why it matches: Similar story and style · both comedy & romance
Menorah in the Middle (2022)
Sarah is headed back to her hometown for Hanukkah with news of her engagement. Upon returning she finds out that her father had a heart attack and things have gotten out of hand.
Why it matches: Similar story and style · both romance
Groundhog Day (1993)
A cynical TV weatherman, along with his idealistic producer and his sardonic cameraman, is sent to report on Groundhog Day in the small town of Punxsutawney, where he finds himself repeating the same day over and over.
Why it matches: Similar story and style · both romance & comedy
Worth the HypeMovies like thisThe Apartment (1960)
Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although he often has to deal with the aftermath of their visits, one night he's left with a major problem to solve.
Why it matches: Similar story and style · both comedy & romance
Absolute CinemaMovies like thisLove Actually (2003)
Eight very different couples deal with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisLooking for Her (2022)
Taylor is headed home for the holidays and her family is finally ready to meet her girlfriend "Jess". The only problem is, Jess isn't really her girlfriend. Taylor holds open auditions for someone to play the part for the holidays.
Why it matches: Similar story and style · both romance & comedy
Mickey Saves Christmas (2022)
Mickey, Minnie and their pals attempt to celebrate the perfect Christmas at their snowy cabin. However, when Pluto causes Santa to lose all the presents on his sleigh, the friends travel to the North Pole on a quest to save Christmas.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisF Valentine's Day (2026)
Gina hates her Valentine's Day birthday and travels to Greece to prevent her boyfriend's proposal. With help from vacationers Johnny and his sister Mickey, she schemes to delay it – while questioning her relationship.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisMy Father the Hero (1994)
A teenage girl on vacation in the Bahamas with her divorced father tries to impress a potential boyfriend by saying that her father is actually her lover.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisSilent Night, Lonely Night (1969)
Over the Christmas holidays in a small New England college town, a man and a woman share a brief interlude. He is there to visit his wife, who is a mental patient at the university, and she is there visiting her son, who is a student, after discovering her husband's infidelity.
Why it matches: Similar story and style
Like Christmas on Windmill Way and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Christmas on Windmill Way?
The closest matches to Christmas on Windmill Way are Jingle Around the Clock (2018), Never Kiss a Man in a Christmas Sweater (2020) and 12 Gifts of Christmas (2015). Below are 27 more, each with the reason it matches.
What should I watch after Christmas on Windmill Way?
Start with Jingle Around the Clock (2018), the closest match to Christmas on Windmill Way.
What is the highest-rated movie like Christmas on Windmill Way?
The Apartment (1960), rated 8.2/10 by 2,848 TMDB users.
What is the newest movie like Christmas on Windmill Way?
F Valentine's Day (2026) is the most recent release on this list.
Are there English movies like Christmas on Windmill Way?
Yes: Jingle Around the Clock (2018), Never Kiss a Man in a Christmas Sweater (2020) and 12 Gifts of Christmas (2015).
How are movies similar to Christmas on Windmill Way chosen?
First come films that Trakt’s viewers watch alongside Christmas on Windmill Way, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.