Movies Like Christmas on Chestnut Street

If you liked Christmas on Chestnut Street (2006), a comedy and tv movie movie directed by Anne Wheeler, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy and tv movie
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.
2
Candy Cane Lane (2023)
★ 6/10Also comedy
Determined to win the neighborhood's annual Christmas decorating contest, family man Chris makes a pact with an elf to help him out-do the competition. However, the elf casts a spell bringing the twelve days of…
3
Click & Collect (2018)
★ 6.6/10Also comedy and tv movie
To save his daughter's Christmas, Andrew goes on a road trip with Dev, his neighbour from hell, to buy an elusive Sparklehoof the Unicorn Princess.
4
A Bad Moms Christmas (2017)
★ 6.3/10Also comedy
Amy, Kiki and Carla – three under-appreciated and over-burdened women – rebel against the challenges and expectations of the Super Bowl for mothers: Christmas. And if creating a more perfect holiday for their families…
5
Magic Stocking (2015)
★ 6.5/10Also tv movie
A young widow finds a tattered old Christmas stocking at a Holiday craft sale, but is skeptical of its magic when it seems to create small trinkets on its own.
6
Kristin's Christmas Past (2013)
★ 5.9/10Also tv movie and comedy
Kristin, a cynical 34-year-old, drinks a mysterious champagne on Christmas Eve and wakes up seventeen years in the past, sharing a room with her 17-year-old self. Given the chance to change the worst Christmas of her…
7
Dolly Parton's Christmas on the Square (2020)
★ 5.9/10Also comedy and tv movie
A rich and nasty woman returns to her hometown to evict everyone but discovers the true meaning of Christmas thanks to the local townsfolk – and an actual angel. Features 14 original songs with music and lyrics by…
8
Mickey and Minnie Wish Upon a Christmas (2021)
★ 7/10Also tv movie and comedy
After a series of mishaps, Mickey, Minnie and the gang are separated all over the world and must try to get back to Hot Dog Hills by Christmas Eve. A mysterious and jolly stranger shows up to tell them about The…
9
The Trailer Park Boys Xmas Special (2004)
★ 6.9/10Also comedy and tv movie
In this holiday prequel, it’s 1997 and Sunnyvale Trailer Park is getting ready for the holiday season. Julian’s got a great idea to make money this Christmas, Ricky gets confused between God and Santa, and Bubbles…
10
29th Street (1991)
★ 6.9/10Also comedy
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.
11
Bah, Humduck!: A Looney Tunes Christmas (2006)
★ 7.1/10Also comedy
In this adaptation of Charles Dickens' A Christmas Carol, Daffy Duck is the greedy proprietor of the Lucky Duck Mega-Mart and all he can think about is the money to be made during the holiday season.
12
The 12 Days of Christmas Eve (2022)
★ 6.1/10Also tv movie and comedy
When Brian Conway, a successful businessman whose family relationships have suffered, gets in a car accident on Christmas Eve, Santa gives him twelve chances to redo the day and repair the relationships in his life…
13
Clear History (2013)
★ 6.1/10Also comedy and tv movie
Nathan Flomm, in order to avoid the humiliation of having missed out on a hugely successful business, assumes a new identity on Martha's Vineyard. He plots revenge when his former business partner moves to the same town.
14
Pee-wee's Playhouse Christmas Special (1988)
★ 7.2/10Also comedy and tv movie
Pee-wee Herman and pals are celebrating Christmas in the Playhouse in their own creative ways: Pee-wee makes a list for Santa Claus 1.5 miles long, teaches Little Richard how to ice skate, goes for a sleigh ride with…
15
To Grandmother's House We Go (1992)
★ 6.5/10Also comedy and tv movie
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.
16
John Mulaney: Kid Gorgeous at Radio City (2018)
★ 7.9/10Also comedy and tv movie
John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.
17
Ricky Gervais: Mortality (2025)
★ 7/10Also comedy and tv movie
Ricky Gervais tackles life, death and the state of the world in a brutally honest special that spares no topic, even his own mortality.
18
Psych: The Movie (2017)
★ 7.2/10Also comedy and tv movie
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and…
19
A Christmas Story Christmas (2022)
★ 6.3/10Also comedy
Follows Ralphie, now adult, who returns to the house on Cleveland Street to give his kids a magical Christmas like the one he had as a child, reconnecting with childhood friends, and reconciling the passing of his Old…
20
Dashing Through the Snow (2023)
★ 6.1/10Also comedy
Eddie Garrick is a good-hearted man who has lost his belief in the wonder of Christmas. While spending time with his nine-year-old daughter Charlotte on Christmas Eve, he befriends a mysterious man in a red suit named…