Best Winter Vacations in the US

While many of us prefer to hibernate in the cooler winter months, for close to 25% of Americans, winter is their vacation season of choice.

In some cases, they're visiting family for the holidays. In other cases, they’re escaping their cold climes for warmer places like Hawaii — arguably a spot for the best winter vacations in the US.

Or vice versa. After all, snow sport-obsessed Floridians need somewhere to set their skis into the powder.

Whether you’re looking for a healthy dose of sun, surf, and sand or just somewhere to cozy up next to a fire with a board game and a steaming cup of cocoa, we’ve got you covered.

Read on for our picks.

Kauai, Hawaii

If you’re keen to get out into some unspoiled nature this winter, look no further than Kauai. This verdant tropical paradise is one of the more remote Hawaiian Islands, which means it boasts far more untouched landscapes than other islands in the Pacific archipelago.

The island boasts a 63-mile coastline dotted with more sandy beaches and exploration-worthy coves than you could visit in a week. Be sure to pack your diving or snorkeling gear so you’re set to admire the underwater reefs and colorful tropical fish up close.

To really get in amongst the rainforest foliage, head to the Nāpali Coast State Wilderness Park, where you can bathe in waterfalls or hike the Waimea Canyon for stunning views.

As you can probably tell, Kauai is best suited to those looking for an active winter vacation!

Falmouth, Massachusetts

Cape Cod is an undeniably pretty place in summer, but did you know it’s equally one of America’s loveliest winter vacation destinations? Between world-class gardens, beach strolls, and boutique shopping, you certainly won’t get bored. Plus, you get to avoid the crowds the warmer weather attracts.

For safe family exercise, rent skis and head out for cross-country skiing on the Shining Sea Bikeway. As the name implies the bikeway takes you through salt marshes, bogs, ponds, and even a pumping station. It runs for just over 10 miles, so there’s plenty of adventure to be had.

If you stay in North Falmouth, you’re a hop, skip, and jump from the picturesque North Falmouth VillageHistoric District. Take an afternoon stroll around this historically listed area and admire American architectural styles from the early 19th to early 20thcentury.

Seabrook Island, South Carolina

Seabrook Island is arguably one of South Carolina’s best-kept secrets.

The remote barrier island sits amongst wildlife preserves, luxury resorts, private living communities, and golf courses — not to mention the pristine beaches. Those who vacation on SeabrookIsland can expect seclusion since the island and its beaches are only open to residents and guests.

Given the mild weather, staying fit while on vacation is easy: try your hand at horse riding, hop on a bike and tackle the trails, or simply go for a jog down the beach. You can eat at the beach club or grab snacks from the neighborhood store.

Nearby, on Kiawah Island, is Freshfields Village, head there for shopping, restaurants, and entertainment.

Woodstock, Vermont

Quaint Woodstock, Vermont, couldn’t be more “New England” if it tried.

And it’s doubly delightful in the winter when snow covers the homes, trees, and rolling hills. In fact, just this year, Conde Nast Traveler listed it as one of the country’s27 “most beautiful towns.”

Most people who visit this town in winter come for the snow, whether snowshoeing at the WoodstockNordic Center, heading to nearby Killington to hit the slopes, or curling up in a cozy cafe admiring it.

For the kids, there are a ton of fascinating museums to visit (we particularly recommend the Vermont Institute of Natural Science) — with the bonus, you can stay warm inside! Woodstock residents take their Christmas light displays seriously; bundle up and stroll or drive the streets to admire them.

There is also a bunch of winter vacation in Vermont-themed festivals to enjoy, from the Maple Sugar OpenHouse Week to Wassail Weekend.

Scottsdale, Arizona

If you’re looking for sunny days and temperate weather for your winter vacay, consider booking some accommodation in Scottsdale, Arizona.

First up, the city boasts a bustling historic center, aptly named “Old Town,” packed with shopping, eateries, and cultural sites. Art lovers are well catered for with the Scottsdale Museum of Contemporary Art, and there’s also the Scottsdale’sMuseum of the West to keep you occupied indoors.

Of course, though, the main reason people travel to Scottsdale is the year-round golfing. The area is home to over 200 courses.

Scottsdale is widely considered a luxury tourism spot, so it boasts several 5-star hotels and resorts replete with swimming pools, restaurants, spas, and unique desert views.

Frankenmuth, Michigan

Even the biggest Grinch will find the joy of Christmas in Frankenmuth. A winter vacation in Michigan is the best place in America to experience a European-style festive season.

This adorable Michigantown is charmingly known as “Little Bavaria” — for good reason. The original settlers hailed from that part of Germany, and today, Frankenmuth is still filled with everything Bavarian, from the food to the architecture.

If you want to learn more about the area’s history, schedule some time out of the cold at the Frankenmuth Historical Museum. You can also warm your belly on chicken dinner, German noodles, or fresh-made crepes.

Those keen to get their heart pumping can don a pair of ice skates and hit the outdoor rink. Or, if you prefer to admire the snow from afar, take a ride through the streets on a horse-drawn carriage.

New York City, New York

If you’re stuck on where to vacation in the winter, a trip to the Big Apple is guaranteed to make everyone in your group happy.

With snow falling on the skyscrapers and busy city streets, you might think this metropolis closes down in the winter. Far from it! In fact, some consider winter in New York City’s most exciting time of year.

Kids will love marveling at all the festive season cheer, from the enormous Rockefeller Center ChristmasTree to the iconic New Year’s Eve ball drop in Times Square. Brooklyn homes also famously light up for the season, and a little later, there are lion dances and firecrackers in Chinatown for the Chinese New Year.

Let’s not forget that NYC is home to some of the world’s most prestigious museums — a visit to any of them is sure to warm your brain and body.

Stay in Manhattan; from there, it’ll be easy to visit every borough and tourist site.

Galveston, Texas

Are you looking for winter vacations in warm climates? Then, add Galveston, Texas, to your bucket list. It’s not called the “Winter Wonderland of Texas” for nothing!

Galveston sits on theTexas Coast and, conveniently, is just a one-hour drive from Houston. There are beaches to stroll down, seaside eateries to chow down in, and festivals to participate in. The street event Dickens on The Strand takes London, England, in the Victorian era as its theme, so expect to see bagpipe players, carolers, and even Queen Victoria herself!

You could also use the town as a launching pad for your next cruise. Many liners depart from the Galveston port, including those run by Royal Caribbean, Carnival, and Disney.

Seagrove Beach, Florida

Winter on 30A means the Gulf water temperatures are cool, still warm enough to swim, and calm. It’s a great time of year for stand-up paddle boarding and kayaking enthusiasts as the Gulf and lakes are smooth as glass. Fishing along the beaches of 30A is world-class year-round.

Seagrove Beach is the quieter, more natural version of its famous neighbor, Seaside. Those who choose to stay in Seagrove Beach are looking for lots of downtime - chilling with family, swimming in the aqua ocean, and grilling in the backyard.

Of course, there are other things to do in Seagrove! The town is close to several state parks and forests, including Deer Lake, Edens Garden, Point Washington, and GraytonBeach. Those looking for adventure can rent watersports equipment or head out for a ride along the 30A.

Seagrove is also conveniently located right amid everything, so visiting other beaches and towns is easy.

Make Memories in the Best WinterVacations in the US

Is a winter wonderland or fun in the sun your idea of the best winter vacation in the US?

Thankfully, the US is so geographically diverse that there’s something for everyone! From the icy north to the tropical south, not to mention offshore locales like Hawaii, all that is left for you to do is decide whether to pack your snorkeling or snowboarding gear!

If you visit and fall in love with one of these winter locales, you may want more permanent vacation accommodation. Lifestyle Asset Group is dedicated to providing real estate investors at all scales a lifetime of memories — and affordable profit potential. We fairly distribute seasonal weeks to our property investors with a rotational calendar.

Are you curious to learn more about our property co-owner options?

Get in touch with us Today

Karla Jones: karla@lifestyleassetgroup.com

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