Whether you are an educator of kids in a school or home setting or just a parent or caregiver trying to find ways to entertain kids Winter Holiday (Christmas, Chanukah, Kwanzaa) themed books and movies are great for education and/or entertainment during the month of December.  The educational value of books is mostly based on giving kids something interesting to read in order to encourage them to learn to read and improve their reading skills.  Some of the books mentioned also offer educational value in other ways as they include aspects of other subjects such as math and history.  Most of the movies are more for entertainment, but certain ones do have educational value as well.

Books

Cheerios Christmas Play Book by Lee Wade: This book is mostly geared towards babies learning to eat with their hands, but it can also be used to teach basic math concepts and can be fun for younger kids.

Latkes and Applesauce by Fran Manushkin (review link): This is a good winter story about a families celebration of Chanukah.  In the story the family is not in the best of circumstances, but they still make due with what they have and enjoy the season with each other.  It is good for teaching kids about Chanukah whether by discussing how your family celebration of Chanukah is similar and different or just teaching kids that do not celebrate Chanukah about a holiday that is different from the one they celebrate, but shares the value of their holiday in at least the importance of bringing the family together.

Merry Christmas, World  by Gibbs Davis: This book is based on the characters from the Full House TV show, in particular Michelle.  In this chapter book Michelle tries to do the most environmentally friendly things in order to win a contest and along the way learns the importance of helping the environment.  Great way to teach kids some environmentally friendly activities for holiday fun.

Rugrats Babies in Toyland by Sarah Willson: This is a great book that teaches the value of being together during the holiday season.  In this book kids also learn the importance of giving, as is learned through Angelica's realization.

Rugrats' Book of Chanukah by Sarah Willson: This is a good kids book about the story behind the celebration of Chanukah.  This is great for kids who belong to a family that celebrates Chanukah to relate to their family traditions a little.  Also, great for kids whose family celebrate other holidays to learn about another winter holiday not their own.

The Case of the Candy Cane Clue: This is a Mary-Kate and Ashley Olsen trenchcoat twin mystery chapter book with a holiday theme.  In the book they are at a sleepover in a toy store when the last remaining toy of the year on earth in stolen and they must discover the theif before the store unlocks in the morning and they and their friends are wrongly blamed for stealing it.

The Case of the Hidden Holiday Riddle: This is another holiday themed Mary-Kate and Ashley Olsen mystery chapter book.  This one is about them being on a riddle treasure hunt and trying to discover who is cheating.  Great for kids to read themselves or to read to them if they are not ready to read a chapter book to themselves.

The First Christmas: This is a good board book for young kids that teaches about the story behind the Christian holiday of Christmas.  This is great for teaching the tradition behind the holiday that a kids family celebrates or to teach kids who do not celebrate Christmas about a holiday some of their peers may celebrate.

The Story of Kwanzaa by Donna L. Washington:  This is a great book for kids that explains the history behind the holiday Kwanzaa.  It also explains some of the Kwanzaa holiday traditions.  This is a good book for teaching kids about Kwanzaa whether it is a holiday they celebrate or not and comparing the holiday traditions to their own Kwanzaa or other holiday traditions they celebrate.

Movies

Arthur's Perfect Christmas: This is a good movie for kids that teaches a little about the traditions of Christmas, Chanukah, and Kwanzaa, as celebrated by him and his friends.

Barney's Night Before Christmas: A magical imagination adventure featuring Barney and his friend.  This is a great movie for kids to relate to if they celebrate Christmas or to learn a little about Christmas traditions that they may or may not be similar to their own family's.

Disney's Sing Along Songs: The Twelve Days of Christmas: This is a great sing along interactive movie for kids to learn some traditional and non traditional Christmas and winter songs.

Hanukkah Tales and Tunes: This is a musical video that teaches about the story behind Hanukkah and the traditions of the celebration in a way that in easy for kids to understand and appeals to them.

Rugrats's Kwanzaa:  This is a Rugrat's video is a fun episode of the show that teaches a little about the holiday of Kwanzaa.  Great for kids to learn about this holiday whether their family celebrates it or not.

Strawberry Shortcake: Berry, Merry Christmas: This is a great video about Strawberry Shortcake trying to find the perfect present for her friends and in the end learns the best present is being together during the holidays.