Most Similar Movies to Winter in Vail (2020)
If you are looking for movies like Winter in Vail (2020), you might like movies tagged with keyword : romance, love, holiday, christmas, family, heartwarming, small town, healing, lighthearted, female lead, sweet, festive, tradition, hope, rebirth, emotion, relationships, self-discovery, comedy, touching .
Noëlle (2006), Santa Girl (2019), Christmas in Palm Springs (2014), So This Is Christmas (2012), Then Came You (2018), The Tree That Saved Christmas (2014), Love Always, Santa (2016) ... Let's take a look at the following list...

Noëlle (2006)
Shortly before Christmas, Father Jonathan Keene (David Wall) arrives to shut down the church of a fishing village's dwindling parish. Though he is usually dispassionate and efficient when working on such tasks, events take a different turn when he becomes entangled in the lives of the town's eccentric residents.
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Santa Girl (2019)
Santa's daughter gets a chance to attend college for one semester in the 'real' world before heading back to the North Pole to fulfill her duties under her father.
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Christmas in Palm Springs (2014)
Jessica has a big presentation in Palm Springs. There are a couple of problems though: her two kids who will do anything to get mom and dad back together again - even if they have to hack mom's phone or pose as a secretary to make sure dad's in Palm Springs too. And father Joe who'll do anything to charm his way back into Jessica's life.
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So This Is Christmas (2012)
Ashley lives in the fast lane until a handyman invades her life and she's directing a Christmas play for underprivileged kids. She finds her soulmate and they might live happily-ever-after--unless her stepbrother gets her killed.
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Then Came You (2018)
A hypochondriac working as an airport baggage handler is forced to confront his fears when a British teenager with a terminal illness enlists him to help her carry out her eccentric bucket list.
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The Tree That Saved Christmas (2014)
Jadin meets Ashley, the con. This story uses the best comedic gaffs--nosy neighbors, hearing voices in your head, and having one's house taken over by con artists. It is rich in humor and self-inflicted misery that ends happily ever after.
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Love Always, Santa (2016)
A widow's daughter writes to Santa Claus, asking for her mother to find love again. When a struggling writer receives the letter, he finds new inspiration and the beginnings of a romance.
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The Christmas Calendar (2017)
When Emily, a struggling baker in a small town, receives a handmade Christmas Calendar from a secret admirer, the local residents become obsessed with finding out the identity of the sender.
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Christmas Solo (2017)
A mischievous, swag-obsessed boy must overcome his inner Scrooge, or remain caught in a cycle where everyday is a Christmas without presents.
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The Christmas Wish (1998)
A Wall Street businessman (Neil Patrick Harris) returns home to help his recently widowed grandmother (Debbie Reynolds).
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The Holiday (2006)
Two women troubled with guy-problems swap homes in each other's countries, where they each meet a local guy and fall in love.
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Wrapped Up in Christmas (2017)
With Christmas just around the corner, 8-year-old Molly asks the mall Santa to find a boyfriend for her beloved aunt.
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Christmas Angel (2009)
Ashley feels alone at Christmas as she searches for a job. Her neighbor Nick offers her a job as his assistant in the best work: helping others. There's one catch she can't tell anyone that her new boss is a sort of Secret Santa.
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Leap Year (2010)
Anna Brady plans to travel to Dublin, Ireland to propose marriage to her boyfriend Jeremy on Leap Day, because, according to Irish tradition, a man who receives a marriage proposal on a leap day must accept it.
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Love Takes Flight (2019)
Straight out of MoVal, a multi-cultural suburb in California, James plays guitar in his room and hides from his emotionally unstable single-father whose fantasy baseball obsession and romantic life render him intolerable. Once tenth grade begins at Vista Christian High School, James is reunited with his unlikely best friend, Abe, a wildchild whose antics draw a lot of...Read all
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Sweet Home Carolina (2017)
Diane is a struggling single mom in LA. Just when things are at their worst, but she will have to live in small town USA for a year and take care of a dog for a year before the house is hers.
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The Christmas Reunion (2016)
The mid-west town of Cave City, Kentucky is preparing for its annual Christmas festival, when festivities are disrupted by a sudden snowstorm. While sitting out the blizzard, a group of former friends who have returned for a high school reunion discover what has happened in the intervening years.
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The Christmas Cure (2017)
A doctor returns home for Christmas to find that her father has decided to retire from his own practice. After reuniting with her high school sweetheart, she wonders if she should stay and take over her father's practice.
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