Movies like Winnie's Vacation (1927)
The best movies like Winnie's Vacation (1927) are Babes (2024), God: Serengeti (2017) and Driver's Ed (2026). If Winnie's Vacation hooked you with its comedy, these 20 similar films are what to watch next, and every pick says why it matches.
Winnie's Vacation
Quick picks
- Highest ratedMerry Christmas, Drake & Josh (2008)7.3/10 from 241 votes
- NewestDriver's Ed (2026)Released 2026
Babes (2024)
After getting pregnant from a one-night stand, a single woman leans on her married best friend and mother of two to guide her through gestation and beyond.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGod: Serengeti (2017)
God presides over a prehistoric tribe.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDriver's Ed (2026)
A group of teens hit the road in a stolen driver's ed car, racing against time to help a lovesick high school senior track down his college-freshman girlfriend and win her back.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisTo Grandmother's House We Go (1992)
When precocious twins Sarah and Julie feel like Mom is tired of them, they take off on an exciting adventure to their grandmother's house and encounter a pair of villains along the way.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisClass Rank (2017)
Two high school misfits join forces in an attempt to overtake the local school board. Guided by their families, they enter the perilous word of politics and, in the process, learn a thing or two about love.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisEenie Meanie (2025)
A former teenage getaway driver gets dragged back into her unsavory past when a former employer offers her a chance to save the life of her chronically unreliable ex-boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHollywood or Bust (1956)
The last movie with Jerry Lewis and Dean Martin together, is a satire of the life in Hollywood. Steve Wiley is a deceiver who cheats Malcolm Smith when he wins a car, claiming that he won it too. Trying to steal the car, Steve tells Malcolm that he lives in Hollywood, next to Anita Ekberg's. When Malcom hears that, they both set out for Hollywood and the adventure begins...
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHello (2013)
The film tells the story of three best friends named Ako, Aki and Awang, who are well-known in their village for their mischievous and humourous pranks. The trio work for Pak Man. One day, they are assigned to pick up his daughter Misha, who has just returned from overseas and dreams of becoming a doctor. The trio have been in love with her for a long time but she does not pay them any heed. When Misha is robbed by a snatch thief one day, she is rescued by a doctor named Shafiq. Her face reminds the doctor of his late wife, and he begins to pursue her, which annoys the trio.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisShane Gillis: Beautiful Dogs (2023)
In a rowdy stand-up set, Shane Gillis riffs on his girlfriend's Navy SEAL ex, touring George Washington's house and being bullied by an Australian Goth.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like this29th Street (1991)
After winning $6.2 million in the 1976 New York State Lottery, he is arrested for throwing rocks at a church. He then tells his story at the police station.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisHeld Up (1999)
What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is taken hostage in a stickup at the local Sip and Zip.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisJackass Presents: Bad Grandpa (2013)
86-year-old Irving Zisman is on a journey across America with the most unlikely companion: his 8 year-old grandson, Billy.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisFun with Dick and Jane (1977)
When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisChief Daddy 2: Going for Broke (2021)
The Beecroft family are ready to spend all of Chief Daddy's inheritance, but not if the CEO of his company has anything to do with it.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisSextuplets (2019)
Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their remaining long-lost siblings.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMVP 2: Most Vertical Primate (2001)
MVP 2 opens with the lovable Jack being ousted from his hockey team, the Seattle Simians, and having to hit the road after being falsely accused of league misconduct. Jack ends up in the city, where he's befriended by Ben, a homeless skateboarder, and Ollie, a skate shop owner. Jack proves to be as adept at mastering the half-pipe as he does at delivering a slap shot, and before long, he and Ben are crashing amateur skateboarder competitions all over the country.
Why it matches: Recommended by TMDB viewers · both comedy
SnoozefestMovies like thisTaking Care of Business (1990)
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisGodspell (1973)
In modern-day New York City, John the Baptist calls out to a group of young men and women to learn from the teachings of Jesus. Through song and dance, they relive Christ's crucifixion.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisMerry Christmas, Drake & Josh (2008)
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.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisNational Lampoon's Vacation (1983)
Clark Griswold is on a quest to take his family to the Walley World theme park for a vacation, but things don't go exactly as planned.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Winnie's Vacation?
The closest matches to Winnie's Vacation are Babes (2024), God: Serengeti (2017) and Driver's Ed (2026). Below are 17 more, each with the reason it matches.
What should I watch after Winnie's Vacation?
Start with Babes (2024), the closest match to Winnie's Vacation.
What is the highest-rated movie like Winnie's Vacation?
Merry Christmas, Drake & Josh (2008), rated 7.3/10 by 241 TMDB users.
What is the newest movie like Winnie's Vacation?
Driver's Ed (2026) is the most recent release on this list.
Are there English movies like Winnie's Vacation?
Yes: Babes (2024), God: Serengeti (2017) and Driver's Ed (2026).
How are movies similar to Winnie's Vacation chosen?
First come films that Trakt’s viewers watch alongside Winnie's Vacation, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.