Best Places to Travel with Kids for an Unforgettable Winter Getaway

When the temperature drops and the snow starts to fall, winter is the perfect time to plan a family vacation that’s as magical as the season itself. Traveling with kids can feel like a challenge, but the right destination makes all the difference. Legacy Vacation Resorts specializes in creating unforgettable experiences for families, offering locations that blend comfort with access to top attractions. Whether your family loves outdoor adventures, cozy indoor activities, or festive holiday fun, there are incredible places to visit this winter that cater to kids of all ages. Below, we’ve rounded up some of the best destinations for an unforgettable winter getaway with your little ones, including options from Legacy Vacation Resorts and beyond.

1. Steamboat Springs, Colorado

Known as "Ski Town, USA," Steamboat Springs is a winter wonderland that’s perfect for families. The town is home to kid-friendly ski slopes, tubing hills, and plenty of opportunities for snowball fights. Steamboat Springs also features hot springs that the entire family can enjoy after a day of adventure. Legacy Vacation Resorts’ Steamboat Springs location is a great home base, offering cozy accommodations, easy access to the slopes, and amenities designed for families.

Not into skiing? Don’t worry! Families can enjoy horse-drawn sleigh rides, snowshoeing, or simply exploring the charming downtown area filled with shops, restaurants, and holiday lights.

2. Orlando, Florida

If your kids dream of escaping the cold, Orlando is a top destination for family fun. With its world-famous theme parks, including Walt Disney World, Universal Studios, and LEGOLAND, Orlando offers endless entertainment for children. Even in winter, the weather in Orlando remains mild, allowing families to enjoy outdoor attractions without bundling up.

For those looking for family-friendly accommodations, Legacy Vacation Resorts-Orlando is an excellent option. With spacious suites, a heated pool, and proximity to all the major attractions, it’s the perfect place to unwind after a day of adventure.

3. Lake Tahoe, California/Nevada

Lake Tahoe is a spectacular winter destination that combines breathtaking scenery with fun-filled activities for the whole family. The area offers ski resorts with kids' lessons, snow tubing, ice skating, and even snowshoeing trails that cater to beginners. Heavenly Mountain Resort, in particular, has a dedicated family zone where kids can explore gentle slopes in a safe environment.

Off the slopes, families can take scenic gondola rides for panoramic views of the lake and mountains or visit the nearby Tahoe Science Center for educational fun. Lake Tahoe’s charm makes it a must-visit for families during the winter season.

4. Gatlinburg, Tennessee

Nestled in the Great Smoky Mountains, Gatlinburg transforms into a winter paradise during the colder months. Families can explore Ober Mountain’s ski slopes and snow tubing runs or experience a magical ride on the Ober Aerial Tramway. If your kids enjoy animals, don’t miss the Ripley’s Aquarium of the Smokies, which offers interactive exhibits and underwater tunnels.

Gatlinburg’s downtown area comes alive during the winter with holiday lights, festive decorations, and unique shops. It’s a cozy, welcoming destination that’s ideal for families looking to combine outdoor adventures with small-town charm.

5. St. Augustine, Florida

For families seeking a mix of history and relaxation, St. Augustine—the oldest city in the U.S.—offers an enchanting winter escape. While the weather remains mild, the city’s annual Nights of Lights event transforms St. Augustine into a dazzling holiday spectacle. Kids will love the trolley tours, pirate-themed adventures, and exploring Castillo de San Marcos, a historic fortress with plenty of space to roam.

The Local St. Augustine, Legacy Vacation Resorts’ newest location, provides families with comfortable accommodations and easy access to the city’s top attractions. It’s the perfect spot to enjoy a unique winter getaway that combines education and fun.

6. Park City, Utah

If your family loves winter sports, Park City should be at the top of your list. Home to the largest ski resort in the U.S., Park City offers everything from skiing and snowboarding to snowmobiling and ice skating. Many of the slopes cater to beginners, making it an ideal spot for families with young kids.

Park City also features an impressive array of off-slope activities, including the Alpine Coaster, a thrilling ride through the snow-covered mountains, and the interactive exhibits at the Utah Olympic Park. For a touch of history, stroll through the town’s charming Main Street, where you’ll find shops, galleries, and family-friendly dining options.

7. Williamsburg, Virginia

Williamsburg is a unique winter destination where kids can have fun while learning about history. Colonial Williamsburg brings the past to life with interactive exhibits, costumed interpreters, and hands-on activities that immerse kids in the 18th century. During the winter months, the town is adorned with festive decorations, creating a warm and inviting atmosphere.

Nearby Busch Gardens also hosts its annual Christmas Town event, featuring holiday-themed rides, shows, and attractions that the whole family will love. Williamsburg’s blend of history, culture, and seasonal magic makes it a standout destination for families.

8. Bretton Woods, New Hampshire

For families who love the charm of New England winters, Bretton Woods is a fantastic choice. This small town offers family-friendly ski slopes, sleigh rides, and snowshoeing trails. Kids will especially enjoy the nearby Mount Washington Resort, which hosts winter-themed activities, including gingerbread house decorating and storytime sessions.

Bretton Woods is also a great destination for families who want to experience the classic holiday spirit. The surrounding White Mountains provide a stunning backdrop for winter hikes and scenic drives.

9. New York City, New York

No winter destination list is complete without New York City. While it might not seem like a kid-friendly option at first glance, the city offers plenty of magical experiences for families during the winter. Ice skate under the Rockefeller Center Christmas tree, visit the holiday markets, or watch a performance of "The Nutcracker" by the New York City Ballet.

For a hands-on experience, take your kids to the American Museum of Natural History or the interactive Children’s Museum of Manhattan. And, of course, don’t forget the wonder of seeing the city’s famous holiday window displays. While the city can be bustling, its winter charm is undeniable.

10. Breckenridge, Colorado

Breckenridge is another Colorado gem that’s perfect for family winter getaways. In addition to skiing and snowboarding, Breckenridge offers snow sculpture exhibits, dog sledding tours, and even winter zip-lining. The town’s historic district is decorated with lights and filled with quaint shops and restaurants that welcome families.

Breckenridge also hosts the Ullr Fest, a celebration of winter that includes parades, contests, and family-friendly activities. It’s a destination that combines adventure with a festive spirit, making it a memorable spot for a winter vacation.

Plan Your Winter Family Getaway Today

Winter is the perfect season to create lasting memories with your kids, and the right destination can make your vacation truly unforgettable. Whether you’re hitting the slopes in Colorado, soaking up the sun in Florida, or exploring historic landmarks in Virginia, there’s something for every family to enjoy.

Legacy Vacation Resorts offers family-friendly accommodations in some of these incredible destinations, providing the comfort and convenience you need for a stress-free getaway. Start planning your winter adventure today and give your kids a vacation they’ll cherish for years to come.