4 Amazing Cities for a Wonderful Winter Vacation

winter vacation
Cold weather = warm memories

Snow-covered scenery. Seasonal festivals and events. Winter trips are uniquely magical experiences, combining the excitement of snow sports with the cozy warmth of indoor pursuits. And cold-weather enthusiasts come alive at the very thought of a winter vacation, booking flights at the first sign of a snowflake.

Ready for a dose of winter charm? Check out our favorite winter destinations.

  • Burlington, VT

    Cute downtown. Scenic views. Tons of snow.

    Burlington has everything you’d expect from a winter vacation, and then some!

    Spend your time wandering around the welcoming city itself, especially its Church Street Marketplace. This pedestrian-only location area is filled with unique shops, cozy cafes, and delicious restaurants. You’ll also find street entertainers, lively events, and food trucks – even in the winter.

    Need more reasons to visit? This picturesque winter destination is located on the shores of Lake Champlain, which often freezes over and allows for outdoor activities such as ice skating and ice fishing.

    And Burlington is within a short drive from 5 ski resorts, making it the perfect home base for your ski vacay.

    Best winter vacation for: combining the city and the slopes

  • Chicago, IL

    Winters in Chicago have something for everyone!

    The city’s usual hustle and bustle is muted by the cool weather, becoming a serene, snow-covered landscape.

    The city’s parks and lakefront provide beautiful spots for winter walks and photo opportunities. And make sure you head over to Millenium Park, where you can ice skate outdoors while gazing at the Chicago skyline.

    Or stay warm inside while partaking in Chi-town’s cultural scene. The city is known for its live music performances, from the Chicago Symphony Orchestra to one of its swanky jazz clubs. Other cultural treasures include the Field Museum and the Art Institute of Chicago.

    Best winter vacation for: an awesome mix of activities, indoors and out

  • Portland, OR

    The colder the weather, the cozier the city!

    Portland’s (relatively) milder weather makes outdoor adventures a bit more pleasant than places with more extreme temps. Bundle up and explore the winter beauty of the Pacific Northwest. Forest Park, one of the country’s largest urban parks.

    As a leader in the world of craft beer, Portland’s breweries often release unique seasonal brews. The cozy ambiance of the city’s taprooms makes them the ideal choice for spending a frosty winter evening.

    Locals are especially friendly in Portland. Spend time in the city’s charming coffee shops or lively music venues, and you’ll no doubt leave the PNW with some new friends!

    Best winter vacation for: warming up with a cold one

  • Vail, CO

    One of the largest ski resorts in the U.S. – how could we possibly leave Vail off our list of winter destinations?

    Vail is, of course, one of the premier ski resorts in the country, with runs for everyone, from groomed beginner trails all the way to challenging backcountry terrain. Non-skiers can have fun with other winter offerings: snowshoeing, ice skating, snowmobiling, and more.

    But what truly sets Vail apart is the cozy village, which looks and feels like a European mountain town. Think cobblestone pedestrian-friendly streets, a village square, and classic alpine architecture.

    And despite its lively après-ski scene, Vail is surprisingly a great location for kids. There are plenty of activities and offerings for children, including ski schools and family-friendly restaurants.

    Best winter vacation for: enjoying European charm, no passport required

Whether you’re a fan of winter sports or prefer cozy indoor events, a winter vacation can be a wonderfully rewarding experience.

And to make sure your winter getaway leaves you feeling refreshed, not stressed, ship your luggage to your hotel or Airbnb with LugLess. You can skip the lines at the airport, breeze right by baggage claim, and go straight to your frost-covered fun!