Movies like The Holiday Calendar (2018)
The best movies like The Holiday Calendar (2018) are Christmas Inheritance (2017), Jingle Around the Clock (2018) and Entertaining Christmas (2018). If The Holiday Calendar 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 ratedSingle All the Way (2021)6.4/10 from 446 votes
- NewestA Royal Montana Christmas (2025)Released 2025
Christmas Inheritance (2017)
To inherit her father's company, socialite Ellen must first visit his small hometown, where she learns the value of hard work and helping others.
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisJingle 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: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisEntertaining Christmas (2018)
Candace, daughter of lifestyle mogul Liz Livingstone, has never lived up to her mother’s standards. When a young girl posts a video begging Liz to help arrange a special Christmas party, Candace is sent in her place. As she struggles to prove herself worthy of running the company, Candace meets—and begins falling for—the girl’s uncle, a reporter writing an expose on her.
Why it matches: Fans watch both · both romance & family
Christmas in Rome (2019)
An independent-minded American tour guide is fired from her job in Rome just before Christmas. She crosses paths with an American executive named Oliver, who wants to buy a high-end Italian ceramics company. Oliver hires Angela to be his tour guide around the Eternal City, as the owner of the ceramics company won’t sell it to him until he learns “the heart and soul of Rome.” But is there another heart and soul that he may win?
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisChristmas on the Alpaca Farm (2023)
Jess, The Queen of Christmas Sweaters, quits her job at the hottest fashion label in NYC intent on winning a Christmas competition with her own line of sustainable luxury knits. Getting her hands dirty, she teams up with Andrew, a single dad and struggling alpaca farmer, as she helps bring Christmas joy to the farm and love into both of their hearts.
Why it matches: Fans watch both · both comedy & romance
The Mistletoe Promise (2016)
A chance meeting between two strangers who share a disdain for Christmas results in The Mistletoe Promise, a pact to help them navigate their holiday complications - together. But as they spend more time with each other and experience the magic of Christmas the phony couple discovers there may be more to their contract than business.
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisChristmas with You (2022)
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
Why it matches: Fans watch both · both romance & comedy
SnoozefestMovies like thisChristmas Pen Pals (2018)
Following an unexpected breakup weeks before Christmas, Hannah, tech wiz and creator of the dating app, Perfect One, heads home for the holidays, challenged to save her failing business by re-conceiving a new romantic dating model. Upon her return she runs into her high school boyfriend, Sam, who she has carefully avoided for years and reluctantly makes a deal with her dad to sign up for the town’s Christmas Cupid, an anonymous holiday pen pal service. As the season progresses, Hannah is smitten by each beautifully written letter she receives and starts to believe that her Christmas pen pal could be her soul mate.
Why it matches: Fans watch both · both romance
Popcorn FlickMovies like thisSingle All the Way (2021)
Desperate to avoid his family’s judgment about his perpetual single status, Peter convinces his best friend Nick to join him for the holidays and pretend that they’re now in a relationship. But when Peter’s mother sets him up on a blind date with her handsome trainer James, the plan goes awry.
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisTwinkle All the Way (2019)
To pull off a spectacular Christmas-themed wedding, a wedding planner joins forces with the co-owner of a family-run Christmas decoration and house-lighting company.
Why it matches: Fans watch both · both romance & family
Popcorn FlickMovies like thisA Royal Date for Christmas (2023)
Bella Sparks, owner of Bella’s Boutique, takes on a demanding new client named Stefan, who needs to be outfitted for a week of high-stakes meetings and events after his luggage goes missing. Imagine Bella’s reaction when she accidentally discovers Stefan is actually Stefan William Francis Brown, the Duke of Tangford.
Why it matches: Fans watch both · both romance & comedy
SnoozefestMovies like thisCampfire Christmas (2022)
Romance rekindles for Peyton and her closest friends when her parents decide to host a holiday themed reunion before selling their family owned summer camp.
Why it matches: Fans watch both · both comedy & romance
A Vineyard Christmas (2023)
Heather Marques, host of Tannin TV’s popular show: Read Between the Vines, is determined to create the perfect Christmas episode by featuring a unique winery from her hometown in Washington State the specialists in Ice Wine. The only thing standing in her way? Rudy Knobloch, the attractive, stubborn owner of the winery.
Why it matches: Fans watch both · both comedy & romance
A Royal Montana Christmas (2025)
A princess looking to decompress before the holidays heads to a Montana ranch and meets a charming guide.
Why it matches: Fans watch both · both romance & comedy
Lights, Camera, Christmas! (2022)
When a holiday rom-com movie shooting in her town needs a costume designer, Kerry, a local shop owner, steps into the role. While working on the movie, she rediscovers her passion for costume design and finds herself falling for Brad, the film’s famous leading man.
Why it matches: Fans watch both · both comedy & romance
The Christmas Temp (2019)
An out of work artist discovers a special Christmas temp agency that matches her with a handful of festive jobs, but falls into a creative rut while juggling holiday preparations and feelings for the agency's HR manager.
Why it matches: Fans watch both · both romance
Santa Bootcamp (2022)
Hired by shopping mall magnate Ed Mancini to host a Christmas gala for his biggest investors, Emily heads to Santa Bootcamp - to find the perfect Santa and the inspiration she'll need to make the evening a success.
Why it matches: Fans watch both · both comedy & romance
No Sleep 'Til Christmas (2018)
Lizzie, a high-end event planner, lies awake nightly while her devoted fiancé Josh rests peacefully. When a sleep-deprived incident causes her to run into Billy, a low-key bartender who is just as sleepless and frustrated as she is, they discover that they can only fall asleep while next to each other.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies 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: Fans watch both · both family & romance
Popcorn FlickMovies like thisCatering Christmas (2022)
A fledgling caterer, Molly Frost, is hired by Jean Harrison, the perfectionistic director of the renowned Harrison Foundation, to cater this year’s annual Christmas Gala dinner. Things get complicated when Molly falls for Jean’s nephew, Carson, 30s, a travel photographer with no desire to take over the family’s foundation… until his aunt assigns him to the task of making sure the catered dinner goes perfectly.
Why it matches: Fans watch both · both comedy & romance
Popcorn FlickMovies like thisUnwrapping Christmas: Lily's Destiny (2024)
Lily, the marketing guru of All Wrapped Up, believes the universe guides us to our destiny and it appears that it’s guiding her toward a celebrity realtor. However, when she feels an unexpected spark with journalist Sean Whitlock during an interview, her heart starts to question everything. As her chemistry with Sean grows, Lily begins to wonder if he’s the true match she’s been waiting for all along.
Why it matches: Fans watch both · both romance & family
Christmas 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: Fans watch both · both family & romance
Popcorn FlickMovies like thisA Brush with Christmas (2022)
Over the week leading up to Christmas in the town of Bayside, Charlotte tries to capture her own unique style in the local art scene while also helping her mother, run the family restaurant. Disheartened and struggling to find time for her art, Charlotte throws out her latest painting, only to discover that it has been anonymously submitted to the Christmas art festival. It turns out that Wyatt, a visiting artist, stumbled upon her discarded work and is now using the festival’s exposure to find its mysterious creator.
Why it matches: Fans watch both · both romance & comedy
SnoozefestMovies like thisUnlocking Christmas (2020)
When a mysterious key and a holiday riddle arrive on their doorsteps, Kate and Kevin embark on a Christmas romance adventure they’ll never forget.
Why it matches: Fans watch both · both romance
Popcorn FlickMovies like thisSix Degrees of Santa (2022)
Christmas enthusiast Steph, has created a program, Six Degrees of Santa. When Steph's own gift lands in the hands of a leading internet entrepreneur, Jason, he's convinced that the original Santa might be his soul mate.
Why it matches: Fans watch both · both romance & comedy
Coming Home for Christmas (2017)
Lizzie Richfield is at a crossroads when she lands a job as house manager for the exquisite Ashford Estate in the Virginia countryside. While planning one final Christmas Eve gala for the Marley family, Lizzie finds herself drawn to Robert—even as Kip pursues her.
Why it matches: Fans watch both · both romance & comedy
Popcorn FlickMovies like thisCrashing Through the Snow (2021)
Maggie and Sam are crashing Christmas. When he proposes they team up against his sister's perfect Christmas, neither of them are prepared for the blended family challenges that lie ahead.
Why it matches: Fans watch both · both comedy & family
A 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: Fans watch both · both romance & comedy
SnoozefestMovies like thisUnwrapping Christmas: Mia's Prince (2024)
Mia, an accountant at All Wrapped Up, is stunned when local celebrity Beau Cavannagh, who looks just like her favorite romance novel hero, enters her life. Despite her doubts, Beau, an heir to a wealthy family, proves his feelings for her are real, even as his family disapproves. Mia soon finds herself swept up in a fairytale romance that's straight out of her dreams.
Why it matches: Fans watch both · both romance
A Magical Christmas Village (2022)
When Summer’s mother Vivian moves in with her and her young daughter Chloe, her orderly existence is upended. Upon arrival, Vivian sets up an heirloom, miniature Christmas village resembling their town, and tells Chloe it grants Christmas wishes. As Chloe begins setting up the figurines, real-life events seem to mimic the scenes she creates. With a little help from the magic of the Christmas village, the family will be brought closer together and just maybe, Summer will learn to open her heart to love again.
Why it matches: Fans watch both · both comedy & romance
Like The Holiday Calendar and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like The Holiday Calendar?
The closest matches to The Holiday Calendar are Christmas Inheritance (2017), Jingle Around the Clock (2018) and Entertaining Christmas (2018). Below are 27 more, each with the reason it matches.
What should I watch after The Holiday Calendar?
People who watched The Holiday Calendar most often go on to Christmas Inheritance (2017), Jingle Around the Clock (2018) and Entertaining Christmas (2018).
What is the highest-rated movie like The Holiday Calendar?
Single All the Way (2021), rated 6.4/10 by 446 TMDB users.
What is the newest movie like The Holiday Calendar?
A Royal Montana Christmas (2025) is the most recent release on this list.
Are there English movies like The Holiday Calendar?
Yes: Christmas Inheritance (2017), Jingle Around the Clock (2018) and Entertaining Christmas (2018).
How are movies similar to The Holiday Calendar chosen?
First come films that Trakt’s viewers watch alongside The Holiday Calendar, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.