The holiday season is a time for comfort, tradition, and connection. Watching a favorite seasonal movie can be a simple way to unwind, enjoy familiar stories, and share moments with family or friends. Below are ten holiday and winter favorites that bring warmth, humor, and a feel-good spirit to the season.

1. Miracle on 34th Street (1947) 

A true holiday staple, Miracle on 34th Street has a cozy, old-fashioned Christmas feel. It is full of warmth, kindness, and holiday spirit.

Why it’s a good pick: Edmund Gwenn brings a calm, likable charm to Kris Kringle, with Maureen O’Hara and Natalie Wood adding heart to the story. It is a familiar watch that many people enjoy returning to each holiday season.

2. White Christmas (1954) 

White Christmas is a classic holiday pick. It blends music, romance, and a snowy setting, with songs many viewers know by heart.

Why it’s a good pick: The story is light and feel-good, following two former Army buddies who team up with a sister act to put on a show and help a beloved former commander. With cheerful performances, cozy winter scenery, and an easygoing rhythm, it is a festive watch that works well for a relaxed evening.

3. Rudolph the Red-Nosed Reindeer (1964) 

This stop-motion special is a longtime seasonal favorite, with well-known songs, iconic characters, and a snowy setting that fits right into the holidays.

Why it’s a good pick: Narrated by Burl Ives, the special is short, simple, and comforting, making it an easy choice for a quiet holiday afternoon or evening.

4. A Charlie Brown Christmas (1965) 

One of the most recognizable holiday specials, this Peanuts production stands out for its simple animation, humor, and jazz soundtrack.

Why it’s a good pick: It is a fun, family-friendly film with humor, music, and an upbeat message about the season that has made it a go-to choice during the holidays.

5. How the Grinch Stole Christmas (1966) 

A Dr. Seuss holiday classic, this animated film is best known for its rhyming narration, memorable music, and the Grinch’s larger-than-life personality.

Why it’s a good pick: Boris Karloff’s narration is key to what makes it so recognizable, and its short runtime makes it an easy addition to any holiday movie night.

6. A Christmas Story (1983)

A longtime holiday staple, this nostalgic comedy is filled with light-hearted scenes and quotable moments as Ralphie navigates the excitement and chaos of the season.

Why it’s a good pick: Comedic performances from Peter Billingsley and Darren McGavin help make the movie easy to revisit, and it’s just as enjoyable whether you watch from the beginning or catch it halfway through.

7. Home Alone (1990)

A holiday favorite for many families, Home Alone blends broad comedy with festive moments, making it an easy and comfortable watch during the holidays.

Why it’s a good pick: Macaulay Culkin’s comedic performance anchors the movie, while Joe Pesci and Daniel Stern add playful, over-the-top humor that keeps things light and entertaining, even if you’ve seen it more than once.

8. The Santa Clause (1994)

This film has become a modern holiday staple, blending humor and heart with plenty of festive moments. It’s a light, family-friendly watch for anyone who enjoys classic holiday storylines.

Why it’s a good pick: Tim Allen’s lighthearted performance helps set the tone, and the story keeps things moving with an easy, feel-good setup as the family adjusts to an unexpected new Santa. The supporting cast adds to the fun along the way, making it a reliable option when you want something festive, upbeat, and easy to rewatch.

9. It’s a Wonderful Life (1946) 

A timeless holiday film, It’s a Wonderful Life blends small-town warmth with a heartfelt story that builds toward a memorable Christmas Eve.

Why it’s a good pick: The movie follows George Bailey as he looks back on his life and realizes just how much his kindness and choices have mattered. James Stewart brings warmth and sincerity to the role, and the ending delivers the kind of hopeful, feel-good holiday moment that stays with you.

10. Elf (2003) 

Now firmly part of the holiday rotation, Elf is known for its upbeat energy, bright humor, and over-the-top Christmas spirit.

Why it’s a good pick: The story leans into holiday themes like kindness, family, and believing in something good, all with plenty of laughs along the way. Will Ferrell’s playful performance keeps it fun and easy to rewatch year after year.

A Cozy Holiday Season

Whether you’re revisiting longtime favorites or adding a few new titles to your rotation, holiday movies offer a simple way to slow down and enjoy the season. These familiar films are easy to settle into and pair well with quiet evenings at home or shared moments with loved ones.

At Flagship Health, we believe well-being is supported not only through care, but also through the routines and traditions that bring comfort and connection. As the holidays approach, we encourage seniors to take time to relax, enjoy the season, and make time for the moments that matter most.