20 Best Holiday Romance Movies To Watch This Winter

The winter holiday season is a time for family, gratitude, love, and watching movies. The perfect choice for the season — the holiday romance film — is an entire genre of its own, with television networks like Lifetime and Hallmark premiering plenty of new ones to binge each year. Watch on and enjoy as a work-obsessed CEO travels to their small hometown to find the true meaning of Christmas, someone reconnects with a love interest from long ago, or people get stuck somewhere due to a snowstorm. Whichever you watch, there's one thing that is almost guaranteed — there is always a happy ending.

There are the go-to classics that audiences watch over and over again, never tiring of them, while studios and streaming sites introduce new options most years to mix up your holiday viewing. With so many movies out there, how do you decide which romantic comedies to watch this winter, and which to put back on the shelf for another time? It isn't easy, but we've put in the work to make your holiday entertainment preparation a little less complicated. Snuggle up on the sofa with a cup of hot cocoa and a cozy blanket as we share the 20 best holiday romance movies that will warm your heart this winter.

When audiences think of holiday romances, they will almost certainly gravitate toward Christmas movies. But, what about New Year's Eve, the holiday that falls just a week later? In "When Harry Met Sally," the two main characters are pulled together during New Year's Eve parties a year apart — even though they've known each other for a decade and there were plenty of opportunities for them to get together without a Times Square ball drop or fireworks.

Our central couple — Harry (Billy Crystal) and Sally (Meg Ryan) — were always in each other's worlds. They went to the same college and repeatedly dated people close to each other. After five years of decidedly not being friends, everything changes when they reunite in a chance encounter in a bookshop. The next year includes two New Year's Eve parties that start and solidify their romance. 

Considered one of the best romantic comedies of all time, "When Harry Met Sally" is the perfect movie to watch for a romantic that needs a holiday flick in the week leading up to New Year's Eve. With a critic rating of 91% on Rotten Tomatoes, this film is one that should be on your watch list to revisit every holiday season.

Fans of "Twilight" should definitely be adding "Happiest Season" to their holiday watch list. Kristen Stewart stars as Abby, a young woman who has not enjoyed the holidays since the death of her parents. This year, she's spending it with her girlfriend Harper's (Mackenzie Davis) family. The only problem is her girlfriend's family doesn't know she's in a relationship with a woman.

Harper's father Ted (Victor Garber) is running for mayor, which adds a layer of confusion to the occasion. Abby is being passed off as the friend with nowhere to go while being introduced to all of her girlfriend's ex-boyfriends. While some of Harper's behavior catches Abby off-guard — leading her to question how well she really knows her — the film ends on a wonderful note about acceptance and inclusion while the family watches a Christmas movie. 

Most critics gave "Happiest Season" a positive review, with Vox calling it "a cute movie with a lot of heart," while The Chicago Sun describes it as "a guilty pleasure filled with sweetness and warmth." While "Happiest Season" received some criticism for the way it takes the tropes of straight holiday romantic comedies and just applies them to the LGBT+ community, it still resonated with many people, winning the 2021 GLAAD Award for outstanding film (via CNN).

Tom Hanks is known for so many films, but we can't forget his holiday romantic comedy "You've Got Mail." While the movie doesn't just take place at Christmas, the scenes that feature the holiday are some of the most pivotal and romantic. 

Kathleen (Meg Ryan) owns a small, independent bookstore that was opened by her mother. Joe (Tom Hanks) is a member of the Fox family — the owners of a chain of large bookstores, comparable to Barnes and Noble. While they're rivals in the real world, in the digital realm they are email pen pals, becoming great friends and sharing personal anecdotes about their lives. The only catch is the correspondents aren't aware of each other's real-world identities, having met in a virtual chat room before the events of the movie. While one of them figures it out, the other is left in the dark for months until the couple has their happy ending.

"You've Got Mail" is an ideal watch for readers and bookworms during the holiday season and any time of year. The small bookstore gives the movie a cozy vibe, while the constant back and forth between Kathleen and Joe makes for a great rivals-to-lovers story. And it's hard to go wrong when you have the rom-com heavy-hitters Meg Ryan and Tom Hanks in the leading roles.

Branded as a "modern holiday classic" (via HuffPost), "The Holiday" follows two women — both dealt a lousy hand in the romance department — who swap houses for two weeks during the holidays. Away from the troublesome exes and embracing the change of scenery, each finds a new love interest where they're least expecting it and ends up having a happy holiday season.

Iris (Kate Winslet), a journalist in London, is having trouble letting go of her ex-boyfriend (Rufus Sewell) — even after finding out he's engaged during the office Christmas party. Desperate not to spend the holiday season miserable and alone, Iris swaps houses with Amanda (Cameron Diaz), a movie trailer producer living in Los Angeles. Equally unlucky in love, Amanda recently endured an angry break-up with her boyfriend (Edward Burns) — something that brought back troubling memories of her parent's divorce. While in snowy Surrey, Amanda falls in love with Iris' brother Graham (Jude Law), and in sunny Los Angeles, Iris grows closer to Amanda's colleague Miles (Jack Black) — eventually resulting in the four spending New Year's Eve together by the end of the film. 

While critics weren't the biggest fans of the movie, audiences loved it, giving "The Holiday" an 80% on Rotten Tomatoes. Despite its contrivances, "The Holiday" has many relatable life lessons, and whereas holiday films usually see the characters encouraged to return home, it is refreshing to see one that embraces the idea of branching out and getting away from it all somewhere new.

"Operation Christmas Drop" focuses on congressional assistant Erica (Kat Graham) — an overworked killjoy flown to an Air Force base in Guam to determine if it should be shut down. Assigned to show her around is Captain Andrew Jantz (Alexander Ludwig), who is tasked with providing a compelling enough reason for the base to stay open.

As Captain Jantz gives Erica the highlights, he's also prepping for their annual "Christmas drop." The base uses its planes to drop crates of supplies and goods to the islands around them each holiday season, ensuring they have what they need. During her time at the base, Erica attends a party, sees just how much the local people rely on the annual event, and helps with the crate drops herself following a complete change of heart. Of course, it wouldn't be a holiday romantic comedy if Erica and Andrew didn't find their own happy ending along the way, adding an extra layer of sweetness to this surprisingly enjoyable film. 

"Operation Christmas Drop" is different from many of the holiday movie offerings out there. Rather than take place in a snow-laden environment, the scenery is a gorgeous island. That doesn't mean there isn't any snow, but more importantly, the film embraces the idea that the holidays are for giving and for helping — which always makes for a heartwarming watch.

After their flights are canceled and hopes of an international vacation are ruined, Kate (Reese Witherspoon) and Brad (Vince Vaughn) are forced to go home for the holidays instead. There are some complications, however, as both of their parents are divorced, meaning they have four different family celebrations to get to. Now facing the complicated logistics of keeping all the family happy, Kate and Brad are also pushed to consider their own relationship. 

"Four Christmases" follows Kate and Brad not only experiencing a day full of family drama but a journey of learning more about each other, and along the way, secrets are revealed that force them to rethink their choices. Before, they never wanted marriage or kids, but that may change by the end of the day as they realize what they both want in life.

While the movie failed to impress critics, it is notable for featuring a very different premise from the others on this list. Instead of finding love after a bad breakup, or stumbling into their perfect match, Brad and Kate work through their existing relationship, finding out new information about each other to see if they still want to have a future together.

If you're craving another holiday movie with a large ensemble cast similar to "Love Actually," then 2011's "New Year's Eve" is a great pick. If you can get past the poor reviews it received from critics, the unabashedly cheesy film features a cast packed with actors that audiences love, making it worth a watch. Starring Hilary Swank, Zac Efron, Halle Berry, Michelle Pfeiffer, Robert De Niro, and many more, Garry Marshall's second ensemble holiday film — following "Valentine's Day" in 2010 — is a holiday romance to fill the gap between Christmas and New Year. 

With a number of interweaving storylines, the film follows a group making sure everything is ready for the annual ball drop in New York City, a mother trying to convince her daughter to stay in for the night so they can spend time together, and plenty of people falling in and out of love. Some get together for the first time, while others reconnect, but all this happens at the crucial stroke of midnight. Like "Valentine's Day," this film features couples of all ages, meaning every viewer will find a person or couple they connect with.

As traditional as leaving milk and cookies for Santa and giving gifts, it isn't the holidays without watching "Elf." But, what many forget is that between the endlessly quotable lines and joyful Christmas spirit, "Elf" also hides a charming love story. When a human baby accidentally ends up at the North Pole, he's named Buddy and taken in by the kindly Papa Elf (Bob Newhart). Though he grows up thinking he's an elf, he later finds out he's actually a human. 

In addition, after Santa (Edward Asner) tells Buddy (Will Ferrell) that his biological father (James Caan) is on the naughty list, the elf-raised human heads to New York to try and help his father redeem himself. While his new family initially struggles with his eccentricities and quirks, Buddy finds a kindred spirit in Jovie (Zooey Deschanel) — a fellow department store employee — and he quickly falls head over heels. With Jovie amused by Buddy's childlike qualities, and the elf equally smitten, fireworks fly on their first date and a love story for the ages is born. In addition to finding love, Buddy connects with his biological family and creates lasting relationships in the human world, bringing much-needed holiday spirit to a cynical society. If "Elf" wasn't already on your winter movie list, it's time to change that. It's the perfect family film and has cemented itself as a holiday classic for years to come.

"The Best Man Holiday" shows what happens when a group of friends that fell out of touch gets together to celebrate Christmas in New York. Everyone has ventured off on their own paths, with one joining the cast of a reality show, someone recently being let go as a professor from New York University, and one friend even becoming a successful football player. Secrets are revealed, sparks fly, and wires are crossed as the friends reconnect and learn what everyone has been through over the last few years.

There is so much to enjoy in this film, making it one of the best additions to your watchlist. The cast is undeniably impressive, featuring the likes of Taye Diggs, Nia Long, and Regina Hall. In a refreshing change from many Christmas films, "The Best Man Holiday" also received positive reviews from critics, with Time Out's Sam Adams calling it "near-impossible to resist." This holiday treat is a sequel to 1999's "The Best Man," which follows the cast more than ten years before the events of "The Best Man's Holiday." Across both films, the camaraderie of the cast is infectious, making this gang perfect to spend time with for a double feature this holiday season.

It might not be the first holiday film you think of, but "Serendipity" opens just before Christmas in New York City, meaning it easily fits the bill. Sara (Kate Beckinsale) and Jonathan (John Cusack) meet while buying gloves at Bloomingdale's. The two have immediate chemistry but are spoken for, so fate has to take the wheel. They reconnect years later just as Jonathan is about to get married and Sara is engaged. Through a series of events, the two find their happy endings, even if it isn't with the person they anticipated. 

The themes of love and destiny in "Serendipity" ensure that its status as a Christmas movie is clear to see, with Decider calling the film "the best Christmas romantic comedy that everyone forgets is a Christmas romantic comedy." Like "You've Got Mail," the entire story does not take place during the holidays, but the couple does meet and have their first "date" around Christmas time.

The movie received mixed reviews from critics, but the chemistry between Beckinsale and Cusack is deemed one of the film's high points, making it worth a watch. Todd McCarthy wrote for Variety, "Cusack and Beckinsale spark well in the opening reel and remain nothing short of energetic and appealing the rest of the time."