Best movies like Winter Break

Better Than Warm Apple Pie

A unique, carefully handpicked, selection of the best movies like Winter Break Starring Milo Ventimiglia, Eddie Kaye Thomas, Justin Urich, Eddie Mills, and more. If you liked Winter Break then you may also like: Watch It, Not Cool, Out Cold, Ride the Wild Surf, Bart Got a Room and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

movie

Viscerally experience a "year off" in Aspen, Colorado with a group of recent college grads who have elected to defer graduate school and career opportunities to ski, snow-board, climb, party, fall in love and basically live life to its absolute fullest out in this spectacular mountain town.

selected filters: Sort: Default

You may filter the list of movies on this page for a more refined, personalized selection of movies.

Still not sure what to watch click the recommend buttun below to get a movie recommendation selected from all the movies on this list

Know any good movies to watch like Winter Break 2003. With a similar plot or stoyline. Suggest it.

Watch It

Mike, Danny, and Rick are grown men who share a house in Chicago. They take on a fourth house mate, John, who is Mike's estranged first cousin. John's welcome to the house is crowned by his introduction to a game of perpetual pranks called "Watch it!" When not playing pranks on each other, the three men spend their time womanizing, avoiding commitment, treating women badly, and talking about women in the coarsest terms. John, somewhat of a drifter with a fear of commitment, is nonetheless a man apart from this trio of feckless cowards. He takes a shine to Anne, recently jilted by his cousin Mike. Meanwhile, Rick is doing his best to ruin a promising relationship with the fetching and sincere Ellen. How Annie, Ellen, Rick, Mike, and John sort out (or fail to sort out) their social lives becomes the focus of the movie.

Not Cool

Former prom king Scott returns home for Thanksgiving break and gets dumped by his long-term girlfriend. With his world turned upside down, Scott strikes an unlikely friendship with former classmate Tori, an ugly duckling who blossomed in her first semester of college, and they embark on an outrageous adventure through their hometown. But when Scott and Tori start falling in love, they realize that a few months away may have changed them more than they realized.

Out Cold

Rick Rambis and his friends are having the time of their lives on Bull Mountain—until the legendary Papa Muntz' son decides to sell the mountain to a sleazy land developer, have the staff fired and turn Bull Mountain into 'Yuppieville'.

Ride the Wild Surf

A group of friends go to Hawaii during the height of surfing season, to compete with other surf bums and find girlfriends along the way.

Bart Got a Room

Danny Stein, a high school senior at the bottom of the social food chain, needs a prom date. As a cause of anxiety for Danny, Bart Beeber, the nerdiest guy in school, has already found a date. At the same time, Danny's divorced parents are both looking for relationships again.

Breaking Away

Dave, nineteen, has just graduated high school, with his 3 friends, The comical Cyril, the warm hearted but short-tempered Moocher, and the athletic, spiteful but good-hearted Mike. Now, Dave enjoys racing bikes and hopes to race the Italians one day, and even takes up the Italian culture, much to his friends and parents annoyance.

Cheats

While other kids buy into countless hours of studying just so they can get a mark in some teacher's report book, Handsome Davis sees it as nothing more than a system of control over your mind. That's why Handsome and his three best friends Sammy, Victor and the cribsheet genius Applebee have banded together and found ways to cheat on their tests all through their school years.

Genius

Charlie Boyle finds that even his high IQ can't solve all of his problems when he takes on a double life in order to make friends his own age.

Cougar Club

When Spence and Hogan graduate from college, life is bleak. They have to work for heinous divorce lawyers that torture them. Spence has a girlfriend from hell and Hogan just wants to start his life already. As luck would have it, our two young men are presented with an opportunity, they develop a club of young men devoted to the older woman, the "Cougar" if you will.

A Night in the Life of Jimmy Reardon

A recent high school graduate is faced with two options, either go to a business school where his father wants him to go to, or get a full time job. However he decides to defy his father and go to Hawaii. Trouble is he has no money. Along the way he comes to understand his parents and eventually bonds with his father.

Copper Mountain

Two friends travel to a ski resort, with one looking to hit the slopes, while the other spends time trying to pick up women.

4.7 / 10 2006 Comedy
suggested by: user636y779bndf

Fifty Pills

Unless Darren can survive New York's largest drug mogul, write a paper on Dante's "Inferno," escape three thugs chasing the wrong guy and sell fifty pills of ecstasy to make his tuition payment, he'll never date the girl of his dreams.

Lucas

A socially inept fourteen year old experiences heartbreak for the first time when his two best friends -- Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love -- fall for each other.

Out of It

An introverted nerd and a violent jock vie for the attentions of a cheerleader.

5.8 / 10 2000 Drama
suggested by: ThunderingTurtle

The Debut

Filipino-American high school student Ben (Dante Basco) works in a comic book shop to earn money to pay his way into Cal Arts. His father, a postman, is determined that his son--who has won a pre-med scholarship to UCLA--will become a doctor. The eighteenth birthday party of Ben's sister, Rose, sets off a comedic and touching series of events and family struggles that will in turn determine young Ben's future. This fresh independent production from Gene Cajayon presents a lighthearted and warm coming-of-age tale filtered through the eyes of an American subculture rarely seen on film.

Harold

A teenager with an early onset of male-pattern baldness befriends his high school's janitor.

Daria in 'Is It Fall Yet?'

Daria is a 16-year-old girl who is a little too smart and funny to fit in with the crowd. It’s summertime and the livin' is hard. Daria finds herself forced into volunteering at the OK To Cry Corral, a summer camp for the overly sensitive and those who'd like to be.

Listen to Me

It was the best time of their lives. A kid from Oklahoma. An immigrant's daughter. A senator's son, a society girl, and a college professor with a dream. They had one thing in common...the will to win. A group of college debaters learn about the world, friendships, love, dreams and family.

Palo Alto, CA

On their last night of Thanksgiving break, four old friends, now all college freshmen, realize their small town has more meaning than they ever imagined.

Playing for Keeps

An ambitious trio of inner-city high school grads tries to hit the big time by turning a run-down country hotel into a rock & roll resort with around-the-clock music and live entertainment. Standing in their way are fearful townsfolk, unscrupulous businessmen and the tax collector, all threatening to bring the curtain down on the teens' aspirations. But this is one threesome who refuses to give up on their lifelong goal without a fight — and a song.

Who Shot Patakango?

A coming-of-age tale set in Brooklyn during the late '50s which centers around the high school life of a group of teens that have to deal with racial tensions at their interracial vocational high school.

Trippin'

Greg is near the end of his senior year in high school, wanting to go to the prom, eyeing Cinny (the school's beauty with brains) from afar, and regularly trippin', daydreaming about being a big success as a poet, a student, a lover. His mom wants him to apply to colleges, but Greg hasn't a clue. One of his teachers, Mr. Shapic, tries to inspire him, too. He finally figures out he can get close to Cinny if he asks her for help with college applications. But friendship isn't enough, he wants romance and a prom date. So, he tells a few lies and, for awhile, it seems to be working. Then, things fall apart and Greg has to figure out how to put the trippin aside and get real.

Phat Beach

A hefty homeboy borrows his dad's Mercedes and goes to the beach with his friends for wild sun & fun.

Ski Party

Remember the beach movies of the sixties? They're back! Well, not quite, but since Avalon, Hickman, and even Funicello appear in this one, it sure feels right. This time, though, read snow instead of sand and you got it. Ski lodge, to be precise, and though the plot is somewhat inane, with the boys cross-dressing to discover the secret of a friend's success with the girls, it's still a somewhat fun outing.

Ski Patrol

Pops isn't worried about the renewal of the lease for his ski lodge - the safety record is unblemished in spite of the crew of misfits who make up his ski patrol. But a scheming land developer has other plans and the ski patrol is thrust into a skiing showdown in order to save Pops' mountain.

Too Young to Marry

Connecticut high school students Max Doyle and Jessica Carpenter fall in love and feel making love isn't enough, so they brave everyone's objections and get married.

Trojan War

Brad is about to hook up with the girl of his dreams, but runs into a problem, no condom. So Brad sets out into the night to find one, running into many obstacles along the way, while not knowing his best friend, Leah is in love with him.

4.8 / 10 2006 Comedy Drama
suggested by: sunnydisposition

The Lather Effect

On the eve of selling her mother's house, a thirty-something housewife wakes up to a hangover surrounded by her best friends from high school...

The Perfect Score

Six high school seniors decide to break into the Princeton Testing Center so they can steal the answers to their upcoming SAT tests and all get perfect scores.

5.1 / 10 1995 Comedy
suggested by: user685u6s4erw4

Glory Daze

Jack, a soon-to-be graduate, finds he's having a difficult time letting go of the college life -- and decides maybe he doesn't have to. Also questioning whether there's life after college are Jack's roommates: Rob, who fears domestication; comic-strip artist Mickey, who's shy around girls; intellectual party animal Slosh; and perpetual student Dennis.

2.4 / 10 2007 Comedy
suggested by: user8617lp4c9tu

The Weekend

In the spirit of "Superbad" and "Dazed and Confused," "The Weekend" relishes the moments that made being a teenager so excruciatingly painful and fantastic. Over the course of a single weekend, various teenagers discover that, perhaps, they don't yet have it all figured out: Rich kid Jacob throws an elaborate weekend party, Benjamin thinks he's going to marry his hesitant girlfriend...

4.0 / 10 1997 Comedy Drama
suggested by: sunflower

1999

On New Year's Eve 1999, as a group of neurotic characters gather at a Greenwich Village apartment, everyone struggles to come to terms with their identities, relationships, and self-doubts before the millennium turns.

Safe at Home!

A Florida boy (Bryan Russell) tells his Little League buddies that his father knows two New York Yankees (Mickey Mantle, Roger Maris).

True Adolescents

At 34, struggling Seattle musician Sam finds himself broke, jobless and losing touch with the person he wants to become. When his girlfriend kicks him out, he's forced to crash with his aunt Sharon and is reluctantly enlisted to take her teenage son and his friend camping.

Colma: The Musical

In the town of Colma, just south of San Francisco, the dead outnumber the living one thousand to one. Here, one wouldn't expect teenagers to burst out in song, or dance around cemeteries and streets. But, that's exactly what happens. Best pals Rodel, Billy, and Maribel find themselves in a state of limbo; fresh out of high school, they are just beginning to explore a new world of part-time mall jobs and crashing college parties. As newfound revelations and romances challenge their relationships with one another and their parents, the trio must assess what to hold onto, and how to best follow their dreams. It's a love song to the city, and to the residents who dream of a better (and more musical) life.

Surf School

A rag-tag bunch of seniors, complete outsiders at their surf-crazed Laguna Beach High School, decide to crash the biggest team surf contest. In order to prevail, however, they must do one important thing...learn to surf! We're taking your classic Cinderella story into the world of surfing, complete with hi-jinx and the aesthetic beauty of surf mecca Costa Rica, our spectacular set location

Goodbye, Franklin High

Comic melodrama following the day-to-day life of high school senior Will, a promising but naive athlete struggling with choices that could determine his future, romance and family difficulties.

Cougar Hunting

Tells the tale of three buddies in their 20's whose love-lives are in shambles. They go to Aspen to pursue the booming trend of dating cougars: hot older women who prey on hot young guys.

Ski School 2

Dave has been enjoying life until he receives an ex-girlfriend's wedding invitation. Even though Beth dumped him years ago, Dave knows it's their destiny to be together. So Dave embarks on a quest: to save Beth from certain death-by-boredom, return balance to the universe, and maybe get in a little awesome skiing. Dave convinces his buddies to join him in his quest to make things right.

Higher Education

A naive young man from the countryside moves to the big city to study art. Soon he has some strange experiences: His roommate turns out to be the bodyguard-protected son of a mafia boss, his fellow student is desperate to initiate him into love, and his attractive art professor also seems to have it in for him.

Answer This!

Brilliant trivia whiz Paul Tarson is great at answering little questions but horrible at answering the big ones – like what’s he going to do after grad school? When his father withdraws his funding, Paul is forced to confront his future and much procrastinated dissertation deadline…until he discovers the First Annual Ann Arbor Pub Trivia Tournament.

Perfect Opposites

The story of two college graduates from the Midwest who move to Los Angeles, where their love is tested for the first time.

How the Garcia Girls Spent Their Summer

Three generations of women in a Mexican American family experience sexual awakenings over the course of a summer.

Satisfaction

When a young rock group called The Mystery gets its first gig at a club, it's an opportunity to see what life is all about. Fresh out of high school, the rockers are hired by an exclusive beach resort thanks to a faded '60s songwriter. There, they meet with romance and adventure. But street-smart lead singer Jennie Lee faces a dilemma: pursue her budding career or finish high school.

Splinterheads

SPLINTERHEADS introduces Thomas Middleditch as Justin Frost, a twenty-something slacker whose “thing” is that he has no “thing” at all. When a small-time carnival rolls into town, he meets Galaxy (Rachael Taylor), a gorgeous con artist, or “splinterhead,” who has more “things” going for her than anyone he has ever met.

Campus Confidential

School... there is the popular crowd. Teachers favor some students over others. Because of this, Violet decides to start a school paper, which exposes many embarrassing secrets of popular kids who think they run the campus.

5.9 / 10 2012 Comedy
suggested by: user6252kdju4et

Funeral Kings

It's always a good day for a funeral at St. Mark's Middle School. Andy and Charlie, two altar servers, don't just get to miss class anytime a parishioner kicks the bucket, they cut out early and play hooky as soon as the service is over. Eventually their irreverent personalities will put them in a situation that is too big for them to handle.

What Boys Like

Things get crazy fro three groomsmen who make a bet on their way to their best friend's wedding. Can the dedicated swinger resist the ultimate temptation and remain celibate during the hottest weekend on his life? Can the serial monogamist actually go through with his first one night stand? It's up to the stunning bridesmaids who are ready for little misadventures of their own in their wedding that brings new meaning to the words LOVE, HoNOR and OBEY.

Hockey Night

When a young girl wants to join her high school's hockey team as goalie, she meets with resistence, but also gets support, especially from the star forward of the team.

More related lists

Sort results by:

X close
Default
Clear filters
...