Movies like Winter in Vail (2020)
The best movies like Winter in Vail (2020) are Winter Castle (2019), Love on the Slopes (2018) and 'Twas the Text Before Christmas (2023). If Winter in Vail hooked you with its tv movie and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedA Christmas Prince: The Royal Baby (2019)6.3/10 from 577 votes
- NewestSincerely Truly Christmas (2023)Released 2023
Winter Castle (2019)
When Jenny attends her sister’s winter wedding at an ice hotel, her heart melts over the best man, the problem is he unexpectedly brings a “plus one,” seemingly dashing her hopes for a wintery romance.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove on the Slopes (2018)
NYC-based copy editor, Alex, is sent to Ridgeline Resort, an extreme sports outpost, to write a story for a travel writing competition. At first, she fails at everything – much to the chagrin of Cole, an extreme sports enthusiast who thinks this city girl should head back to New York. But when Alex offers to assist Cole with his local arts festival, he reluctantly obliges to be her guide as she faces her fears doing one extreme sport after the next.
Why it matches: Recommended by TMDB viewers · both romance & comedy
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 thisA Cookie Cutter Christmas (2014)
Two longtime rivals and elementary school teachers duke it out during the holidays in a Christmas cookie bake-off, but their real feud ignites over a shared interest in a handsome single dad. With both determined to win the prize and the romance, their competitiveness could jeopardize what matters most this Christmas season.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisChristmas at the Drive-In (2022)
Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies 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 thisChristmas on Windmill Way (2023)
Mia Meijer gets ready for the Christmas Market Dutch Bake-Off and suspects that her grandmother, Ann, will walk away with the cherished Golden Rolling Pin thanks to her Kerststol, a traditional Dutch fruited Christmas bread. But Mia's world is rocked when she learns that Ann was having financial troubles and had to sell the land deed to the Windmill Way property in her family for generations. Making matters worse, the buyer is Mia's former boyfriend, property developer Brady Schaltz, who must let Mia and Ann know the Meijer family-owned heritage Dutch sawmill, renowned for the past 90 years for its fine millwork and beautiful wooden furniture, will be torn down to put up a luxurious resort.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies 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: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA Kindhearted Christmas (2021)
Jamie owns a sightseeing and tour company in the small town of Cooperville, New York. Navigating the holidays with enthusiasm is trickier for Jamie since her husband Matt passed. Matt loved Christmas and found unparalleled joy in giving to others. While reminiscing with family, Jamie realizes the town desperately needs someone with Matt’s genius for thinking of the small gestures that bring genuine happiness to the holidays.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisComing 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: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisChristmas with a View (2018)
This Christmas, Thunder Mountain Ski Resort is abuzz when celebrity chef Shane Roarke is named the new head chef. Clara Garrison isn't as excited and is instead focused on getting resettled after her failed attempt at opening a restaurant in the city. With their paths constantly crossing, will their shared passion for cooking bring them together or will secrets keep them apart?
Why it matches: Recommended by TMDB viewers · both romance
SnoozefestMovies like thisDebbie Macomber's Dashing Through The Snow (2015)
Stranded at an airport at Christmastime, Ashley Harrison accepts a ride from Dash Sutherland, who has just rented the last car in town. As the pair heads north, their adventures include car trouble, adopting a puppy and being secretly tailed by federal agents, who believe Ashley is up to no good. With a hint of romance gradually filling the air will these two fall in love or will their journey bring about an unexpected road bump to romance?
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChristmas in Evergreen: Tidings of Joy (2019)
A skeptical writer shows up in Evergreen to get the scoop on the town's famed passion for Christmas during a search for a long-lost time capsule.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Little Christmas Charm (2020)
Holly, a jewelry designer finds a lost charm bracelet and teams up with investigative reporter Greg in hopes of finding the owner and returning it by Christmas Eve.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisChateau Christmas (2020)
Margot, a world-renowned pianist, returns to Chateau Newhaus to spend the holidays with her family and is reunited with an ex who helps her rediscover her passion for music.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisOne Royal Holiday (2020)
When Anna offers a stranded mother and son shelter in a blizzard, she learns that they are the Royal Family of Galwick. Anna shows the Prince how they do Christmas in her hometown, encouraging him to open his heart and be true to himself.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisFalling for Christmas (2022)
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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
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 Wonderland (2018)
Heidi, who initially left her small town of Pleasant Valley with the dream of one day becoming a successful painter, has put her own art on hold to excel as an art gallery curator. Now, a week before the gallery’s big Christmas party, she must return home to watch her niece and nephew. She comes face to face with her high school love, Chris, now a teacher, and offers to help him find a new last-minute location for the Christmas dance.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisA Very British Christmas (2019)
Opera singer Jessica's flight to her concert in Vienna gets delayed and she is stuck in a remote area of England. The only place to stay is a bed-and-breakfast in an enchanting village run by a handsome widower named Andrew.
Why it matches: Similar story and style · both romance & comedy
Sincerely Truly Christmas (2023)
When a magical Christmas wish goes wrong and inadvertently gives Christina the ability to hear what gifts everyone wants for the holidays, she quickly learns that convincing reclusive one-hit wonder, Dan Copren, to step back into the limelight could make a lot of people happy. But to get to Dan, Christina must first link up with her handsome realtor, Robert, and help him figure out his son Oliver’s ever-changing Christmas wish list.
Why it matches: Similar story and style · both comedy & romance
Green Card (1990)
Urban horticulturalist Brontë Mitchell has her eye on a gorgeous apartment, but the building's board will rent it only to a married couple. Georges Fauré, a waiter from France whose visa is expiring, needs to marry an American woman to stay in the country. Their marriage of convenience turns into a burden when they must live together to allay the suspicions of the immigration service, as the polar opposites grate on each other's nerves.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisKadhal Desam (1996)
Two boys from rival colleges, one rich and the other poor, become good friends after an incident. A new girl in college makes both their hearts melt but neither realises that they love the same girl.
Why it matches: Similar story and style · both comedy & romance
Four Christmases (2008)
Brad and Kate have made something of an art form out of avoiding their families during the holidays, but this year their foolproof plan is about go bust -- big time. Stuck at the city airport after all departing flights are canceled, the couple is embarrassed to see their ruse exposed to the world by an overzealous television reporter. Now, Brad and Kate are left with precious little choice other than to swallow their pride and suffer the rounds.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisSummertime Blues (2009)
The life of 15 year old Alex is turned upside down, when his parents are divorced and find new partners right away. After a fight at school, the mother takes him over to England, where Alex chaotic life continues.
Why it matches: Similar story and style · both comedy & romance
A Christmas Princess (2019)
A struggling chef living in a trendy New York borough, Jessica took over a small restaurant where she used to work as a waitress, but it’s growing tough to make ends meet. Prince Jack, who’s in the city for his family’s annual Christmas charity dinner, finds himself in need of a last-minute chef for the royal event when he meets Jessica. As their relationship evolves and a romance blooms, so do the obstacles. But as the event arrives, she decides to go through with the dinner, and may just get the best Christmas present of all… love.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisLook Who's Talking Now! (1993)
When high-powered executive Samantha LeBon hatches a scheme to spend a romantic Christmas with her new employee – the unsuspecting, blithesome James – his wife, their kids and their two dogs, Rocks and Daphne, must rescue him before he makes a terrible mistake.
Why it matches: Similar story and style · both romance & comedy
SnoozefestMovies like thisBaking Christmas (2019)
When their mother decides to retire, her three children organize Christmas Cake Off to choose which one of them is going to take over the family bakery.
Why it matches: Similar story and style · both comedy
Love Stalk (2016)
Sharon is a fast-rising PR executive from Singapore, searching for love in Hong Kong, who may have found her dream guy, but as she chases after him online and in person, Sharon quickly finds out the dangers of stalking a secret crush.
Why it matches: Similar story and style · both romance & comedy
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Frequently asked questions
What are the best movies like Winter in Vail?
The closest matches to Winter in Vail are Winter Castle (2019), Love on the Slopes (2018) and 'Twas the Text Before Christmas (2023). Below are 27 more, each with the reason it matches.
What should I watch after Winter in Vail?
Start with Winter Castle (2019), the closest match to Winter in Vail.
What is the highest-rated movie like Winter in Vail?
A Christmas Prince: The Royal Baby (2019), rated 6.3/10 by 577 TMDB users.
What is the newest movie like Winter in Vail?
Sincerely Truly Christmas (2023) is the most recent release on this list.
Are there English movies like Winter in Vail?
Yes: Winter Castle (2019), Love on the Slopes (2018) and 'Twas the Text Before Christmas (2023).
How are movies similar to Winter in Vail chosen?
First come films that Trakt’s viewers watch alongside Winter in Vail, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.