Movies Like Christmas on Windmill Way

If you liked Christmas on Windmill Way (2023), a romance and comedy movie directed by Don McBrearty, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy and tv movie
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.
2
Catering Christmas (2022)
★ 6.3/10Also tv movie and comedy
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…
3
Never Kiss a Man in a Christmas Sweater (2020)
★ 6.5/10Also romance and comedy
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.
4
12 Gifts of Christmas (2015)
★ 6.1/10Also tv movie and comedy
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…
5
A Christmas Prince: The Royal Baby (2019)
★ 6.3/10Also romance and tv movie
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.
6
Christmas at Grand Valley (2018)
★ 6.4/10Also tv movie and romance
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…
7
Christmas in Evergreen: Letters to Santa (2018)
★ 6.8/10Also romance and tv movie
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.
8
'Twas the Text Before Christmas (2023)
★ 6.5/10Also romance and comedy
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…
9
Jingle Around the Clock (2018)
★ 6.7/10Also comedy and romance
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…
10
Dolly Parton's Christmas on the Square (2020)
★ 5.9/10Also comedy and tv movie
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…
11
A Merry Christmas Wish (2022)
★ 5.9/10Also tv movie and comedy
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…
12
A Christmas Miracle for Daisy (2021)
★ 5.9/10Also romance and comedy
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…
13
Falling for Christmas (2022)
★ 6.2/10Also romance and comedy
An engaged, spoiled hotel heiress finds herself in the care of a handsome, blue-collar lodge owner and his precocious daughter after getting amnesia in a skiing accident.
14
Sharing Christmas (2017)
★ 6.2/10Also romance and tv movie
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…
15
The Mistle-Tones (2012)
★ 6.1/10Also tv movie and comedy
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…
16
A Glenbrooke Christmas (2020)
★ 6.5/10Also romance and tv movie
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.
17
Kristin's Christmas Past (2013)
★ 5.9/10Also tv movie and comedy
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…
18
Marry Me at Christmas (2017)
★ 6.4/10Also romance and tv movie
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…
19
Christmas Next Door (2017)
★ 6.1/10Also romance and tv movie
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.
20
Poinsettias for Christmas (2018)
★ 6.4/10Also romance and tv movie
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…