6 Perfect Cities for a Cozy Winter Vacation

Your guide to winter bliss

When the days are cold, there’s nothing like a cozy winter vacation to warm your soul. Sure, ski trips are popular—and thrilling. And heading south—to thaw out for a bit—is incredibly tempting. But sometimes, you just want to get away, unwind, and enjoy the season’s slower side. It’s your chance to experience winter’s unique magic!

Ready to relax? Bundle up and let the coziness begin at these low-key winter destinations.

• Alexandria, VA

  Located just outside of Washington, D.C., Alexandria is a charming step back into history.

  The heart of the city is the beautifully preserved Old Town Alexandria. Cobblestone streets, gaslamp-style lighting, and 18th-century architecture are teeming with nostalgia—and coziness!

  In the winter, its waterfront district offers stunning views of the Potomac River. For a truly magical winter vibe, grab a hot drink and take a waterfront stroll. The twinkling lights make for a charming end to your evening.

• Boston, MA

  Looking for a culture-rich cozy winter vacation?

  Bundle up and walk along the Freedom Trail, a 2.5-mile walk that winds through some of Boston’s most iconic sights. Or visit the Museum of Fine Arts, for a peaceful—and much warmer!—afternoon.

  If it gets a little too chilly, Boston’s cozy cafes and historic pubs offer a welcoming refuge. The clam chowder at Union Oyster House—the country’s oldest continuously operating restaurant—will warm your body and soul.

• Burlington, VT

  This quintessential New England destination is a picture-perfect winter retreat.

  Tucked into the shores of Lake Champlain and surrounded by majestic mountains, Burlington is ideal for enjoying winter’s quiet side. The entire town is a winter wonderland filled with twinkling lights, unique boutiques, and welcoming cafes.

  Even the farm-to-table dining scene goes winter-happy, featuring hearty dishes made with locally sourced ingredients, such as Vermont Cheddar soup. Meanwhile, craft breweries produce seasonal ales—the perfect dinner accompaniment.

• Leavenworth, WA

  Ready to step into a European snow globe?

  The Alpine-inspired village, surrounded by snow-capped mountains, is a cozy winter vacation destination that feels straight out of a fairy tale! Leavenworth’s Bavarian-themed beer halls serve generous helpings of German cuisine, while cafes offer delicious mugs of mulled wine.

  And if you’re a fan of cold-weather activities, you’re in luck! You can go sledding or cross-country skiing just minutes from downtown. (You know, just like in the old country.)

• Milwaukee, WI

  Let “Brew City” surprise you as a cozy winter vacation spot—it absolutely shines in the colder months!

  Start your trip with a visit to one of the city’s historic breweries, sipping craft beer and enjoying local comfort foods such as cheese curds and beer cheese soup. Then explore the Historic Third Ward—the city’s creative hub—where you can visit art galleries, studios, and boutiques.

  Despite the brisk weather, the laid-back atmosphere and Midwest charm will keep you warm.

• New Orleans, LA

  Let the good times roll in the Big Easy!

  The weather is surprisingly chilly, but much better for exploring than summer’s oppressive heat and humidity. And—if you avoid Mardi Gras—the city is happily uncrowded in the winter.

  Wander around the famous French Quarter, where wrought-iron balconies, cobblestone streets, and glowing gas lamps create an enchanting atmosphere. And when you’re ready to warm up, pop into cozy jazz clubs to enjoy live music by talented local musicians.

If a cozy winter trip is calling your name, these cities deliver the perfect blend of seasonal charm and welcoming warmth!

And to make your winter getaway truly magical, ship your bags to your hotel or Airbnb with LugLess. We’ll take care of your cold-weather gear, so you can travel stress-free. No hauling bags through the airport and no dealing with baggage claim. So you can relax and enjoy the cozy winter vacation of your dreams!