Although summer trips and fall vacations are enjoyable, the winter months are the ideal time for a getaway. This is the perfect moment for a pre-holiday weekend retreat, and once January and February roll around, a change in scenery will be much appreciated. The best part about winter travel is that costs are generally lower, allowing for a bit of indulgence that might not be possible during peak seasons. Whether you’re looking to experience winter sports and après-ski activities or prefer a warm retreat, we have compiled a list of the best winter getaways in the U.S.

Take it from someone who is constantly planning their next vacation: having one of these winter getaways to look forward to will make the upcoming months much more enjoyable. Continue reading for our top recommendations for winter destinations in the U.S., including warm-weather havens, popular ski resorts, and festive cities that come alive during the holidays.

In this article
1 Best City Vacations
2 Best Winter Destinations for Small-Town Charm
3 Best Ski Vacations
4 Best Warm-Weather Getaways

Best City Vacations

For these winter getaways, make sure to pack some warmer clothes and comfortable shoes, as you’ll have plenty of opportunities for dining, exploring bars, and visiting shops. These cities come alive during the holiday season, offering a bustling and festive atmosphere.

Chicago, Illinois

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Chicago, The Everygirl’s hometown, is a must-visit during the winter season. The city transforms into a winter wonderland, offering activities like ice skating in Millenium Park and festive events such as the Christkindlmarket. In addition to its winter charm, Chicago boasts a diverse food scene, cultural attractions like museums and shows, and plenty of entertainment options. Whether you’re into comedy, sports, or exploring, Chicago has something for everyone.

Where to stay: Consider Thompson Hotel (starting from $115) or Viceroy Chicago (starting from $179)

New York, New York

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Winter in New York City is a magical experience, with holiday lights, festive displays, and a myriad of seasonal activities. From ice skating in Central Park to admiring holiday window displays, there’s something enchanting about the city during the winter months. Additionally, January and February offer lower hotel rates and fewer crowds, making it an excellent time to explore the Big Apple.

Where to stay: Check out Walker Hotel Greenwich Village (starting from $166) or Arlo Soho (starting from $179)

Best Winter Destinations for Small-Town Charm

If you’re seeking a cozy winter retreat reminiscent of a Hallmark movie, these small-town destinations are perfect for you.

Leavenworth, Washington

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Step into a picturesque Bavarian village right in the heart of Washington state with a visit to Leavenworth. Adorned with Christmas decorations and lights during the holiday season, this town offers a winter wonderland experience. Visitors can enjoy various winter sports activities or peruse local boutiques for unique gifts. Additionally, do not miss the Nutcracker Museum, showcasing an extensive collection of nutcrackers from around the world.

Where to stay: Consider Bavarian Lodge (starting from $174) or Posthotel (starting from $625)

New Paltz, New York

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New Paltz, known for its quaint downtown area and scenic hiking trails, offers a serene winter escape. History enthusiasts can explore Huguenot Street, while film aficionados can visit Mohonk Mountain House, a historic landmark. This charming town features a plethora of outdoor and indoor activities, making it an ideal retreat for a weekend getaway.

Where to stay: Check out Minnewaska Lodge (starting from $216) or Mohonk Mountain House (starting from $653)

Charleston, South Carolina

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Experience the charm of the South in Charleston, South Carolina, during the winter months. The city hosts various festivals and markets, including the Holiday Festival of Lights, creating a festive atmosphere. Whether you’re exploring the Historic District or enjoying a ghost tour, Charleston offers a unique blend of history, culture, and gastronomy.

Where to stay: Consider French Quarter Inn (starting from $296) or Zero George (starting from $479)

Best Ski Vacations

Whether you enjoy skiing or après-ski activities, these snow-covered destinations offer something for every winter enthusiast.

Park City, Utah

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Park City, Utah, offers a perfect blend of skiing and relaxation, making it an ideal destination for various travel preferences. Whether you’re hitting the slopes or indulging in spa treatments, there’s something for everyone in Park City. Enjoy the vibrant downtown area with its shops, breweries, and dining options, creating a memorable winter getaway.

Where to stay: Explore Hotel Park City, Autograph Collection (starting from $237) or Stein Eriksen Lodge Deer Valley (starting from $462)

Stowe, Vermont

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Stowe, Vermont, is a charming town ideal for winter getaways, even if you’re not into skiing. Enjoy the local breweries, explore downtown Stowe, and soak in the relaxed atmosphere. With reliable shuttle services to the mountains and downtown, navigating the town is convenient. Whether you prefer outdoor adventures or cozying up indoors, Stowe has something special for everyone.

Where to stay: Discover Topnotch Resort (starting from $159) or Green Mountain Inn (starting from $209)

Best Warm-Weather Getaways

If you prefer warmer climates during the winter, these sunny destinations are perfect for your escape.

San Diego, California

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San Diego, California, offers mild winter temperatures, making it an ideal destination for those looking to escape the cold. Outdoor activities like surfing and kayaking are enjoyable year-round, while the city’s cultural attractions and beach neighborhoods provide a diverse range of experiences for visitors.

Where to stay: Consider Pacific Terrace Hotel (starting from $263) or Tower 23 Hotel (starting from $339)

Miami, Florida

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Miami, Florida, provides a perfect tropical escape during the winter months, with its sunny beaches and vibrant city life. Whether you prefer lounging by the pool or exploring the city’s diverse neighborhoods, Miami offers a mix of relaxation and adventure for every type of traveler.

Where to stay: Explore Novotel Miami Brickell (starting from $239) or The Betsy Hotel South Beach (starting from $321)

Palm Springs, California

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Palm Springs, California, offers a warm and relaxing retreat during the winter season, featuring stunning landscapes and luxurious resorts. Whether you’re hiking, shopping, or indulging in spa treatments, Palm Springs provides a serene setting for rejuvenation and relaxation.

Where to stay: Consider Omni Rancho Las Palmas Resort & Spa (starting from $220) or Korakia Pensione (starting from $259)


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