Discover New Books to Read Over Winter Break With Your Kids

Winter break is a time to slow down, cozy up, and make memories as a family. What better way to enjoy the season than to dive into a great book together? Reading with your child creates lovely bonding moments and helps them keep their reading skills sharp. Plus, it’s a chance to check their reading abilities in a low-pressure, relaxed way.

Here are some holiday book recommendations for every age group, along with a few reasons why reading together is so powerful—and what to do if you notice your child might benefit from a little extra reading support.

Preschool (Ages 3–5)

1. How Does Santa Go Down the Chimney? by Mac Barnett and illustrated by Jon Klassen offers a fun look at holiday magic and encourages kids to use their imagination.
2. Oy, Santa!: Or, There’s a Latke to Learn about Hanukkah by Joyce Schriebman and illustrated by Gila von Meissner is a funny, relatable story that introduces young children to Hanukkah traditions in a lighthearted way.
3. The Night Before Kwanzaa by Natasha Wing and Kirsti Jewel and illustrated by Amy Wummer is a festive adaptation of The Night Before Christmas that captures the spirit of Kwanzaa in an accessible, engaging way.
4. The Snowy Day by Ezra Jack Keats is a classic tale that follows Peter as he explores the snow-covered world. It celebrates the wonder of a snowy day through simple, beautiful illustrations.

These books captivate short attention spans with colorful illustrations that make story time magical. Reading with preschoolers actively builds early language skills, expands vocabulary, and sparks the imagination, laying a solid foundation for future reading success.

Elementary (Ages 6–10)

1. The Polar Express written and illustrated by Chris Van Allsburg follows a boy’s journey to the North Pole on a magical train ride that captures the wonder of Christmas.
2. Hershel and the Hanukkah Goblins by Eric A. Kimmel and illustrated by Trina Schart Hyman is a clever story about a traveler who saves a village’s Hanukkah celebrations from goblins and blends holiday magic with a touch of humor.
3. Seven Spools of Thread: A Kwanzaa Story by Angela Shelf Medearis and illustrated by Daniel Minter weaves in the principles of Kwanzaa with a story of unity and cooperation perfect for family discussions.
4. Owl Moon by Jane Yolen and illustrated by John Schoenherr is a beautifully illustrated story about a father and daughter’s quiet winter walk. It captures the magic of snowy nights and family bonds.

These slightly longer books for elementary-aged kids encourage readers to dive deeper into stories. They also offer opportunities to discuss friendship, kindness, and family traditions. As you read, listen to how your child reads aloud or follows along; if they’re having trouble, it might be a good time to support them with a bit of extra practice or reading help.

Middle School (Ages 11–13)

1. The Best Christmas Pageant Ever by Barbara Robinson is a funny, heartwarming story about a family that brings an unexpected twist to the town’s Christmas pageant.
2. Eight Nights of Flirting by Hannah Reynolds is a holiday romance that mixes humor and tradition. It offers middle schoolers a lighthearted, feel-good read.
3. KWANZAA: How to Celebrate it in Your Home by Kathleen M. Taylor and illustrated by Charles A. Taylor II provides everything you need to participate in this unique and remarkable holiday.
4. The Snow Girl by Sophie Anderson and illustrated by Melissa Castrillon is a magical, heartwarming tale inspired by Slavic folklore. In it, a young girl made of snow embarks on an enchanting journey of self-discovery and belonging.

Books for middle schoolers can keep them engaged and reading for extended periods. These titles encourage deeper comprehension and exploration of character, plot, and themes, helping to build critical thinking skills. If your child shows signs of struggling with longer texts, consider reading tutoring to build confidence in reading comprehension.

High School (Ages 14+)

1. Let It Snow by John Green, Maureen Johnson, and Lauren Myracle is a collection of interconnected romantic stories set during a holiday snowstorm. It’s perfect for teens who enjoy romance and a holiday theme.
2. Eight Dates and Nights: A Hanukkah Romance by Betsy Aldredge is a heartfelt romance that explores Jewish holiday traditions, relationships, and family bonds.
3. Practicing Kwanzaa Year Round by Gwynelle Dismukes teaches how the seven principles of Kwanzaa can guide and uplift our daily actions and decisions.
4. The Wood at Midwinter by Susanna Clarke is a mesmerizing tale of magic, mystery, and transformation. It weaves hauntingly beautiful prose with a journey through an enchanted forest at the heart of winter.

High schoolers can handle more complex stories and themes, allowing you to choose books that spark deeper discussions on relationships, identity, and values. Reading with your teen or discussing books they’re reading can give you insights into their interests and any academic needs they might have. Winter break is a great time to ensure they feel confident reading before heading back to school.

Why Reading Together Matters

Reading with your child, regardless of age, is more than just a cozy winter activity (although it’s certainly that, too!). It’s an effective way to help them stay on track with reading skills during the school break, giving them a boost when they return to class. When you read together, you’re modeling reading habits and showing them that books can be both fun and meaningful.

Moreover, reading together can reveal any reading difficulties your child may have without the stress of school assignments. If you notice that your child is stumbling over words, struggling to follow along, or seeming frustrated, winter break can be a perfect time to seek additional support. Programs like K12 Tutoring offer one-to-one sessions tailored to your child, building their confidence and turning reading into something they truly enjoy.

Cozy Up With a Good Book (and Pajamas!)

One family tradition you might enjoy adopting is a visit from the Christmas Eve Fairy. The Christmas Eve Fairy arrives each year in our family, leaving matching pajamas and a book for each family member to cozy up with before bedtime. It’s a magical way to start the holiday, creating a warm and memorable Christmas Eve where everyone snuggles up in their new pajamas with a good book.

This little tradition makes the night before Christmas feel extra special and sets the tone for quality family time, reminding us that the season is about togetherness, warmth, and sharing. Adding books to this tradition lets everyone dive into a story together, and it’s a wonderful way to keep up reading momentum over winter break!

So, as you grab a blanket and settle in this holiday season, don’t forget the magic of new pajamas and a new book—perfect for creating lasting holiday memories.