All Ages

10 Cheap & Fun Winter Break Vacations

Little Boys Sipping Hot Cocoa; Courtesy of mamaza/Shutterstock.com
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Who says you have to wait until next summer to take a vacation? Depending on what part of the country your kids attend school, you might have a winter break in the few weeks before spring break, and/or your kids likely have off for a week or so around the holidays. Take advantage of the time off with a winter break vacation on the cheap.

Aerial View of Cancun; Courtesy of harvard1932/Shutterstock.com

1. Cancun, Mexico 

With so many hotels, resorts, guest houses and family inns to choose from, greater Cancun makes for a popular and inexpensive winter break destination where you can almost always score a deal. You can cut surprise costs out of the equation by opting to stay at an all-inclusive property, where all your meals and drinks (and sometimes even the kids’ club, too!) are covered in rates. Winter is the perfect time of year to head south of the border, with balmy air temperatures and those reliably warm and sapphire waters waiting in Mexico (and the hurricane threat on hold until next season, to boot).

Recommended Hotel: All Ritmo Cancun Resort & Waterpark

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Young Girl Snowboarding at Windham Mountain; Courtesy of Windham Mountain

2. Windham, NY

The Catskills town of Windham Mountain is just two hours from Manhattan and makes for a fun and inexpensive winter break when snow and skiing are top priority for your family. There are 52 trails for skiers and snowboarders to enjoy and you can sleep within a short stroll of the slopes at the Windham Mountain Village. The best part about vacationing here is that lift tickets cost just a fraction of what you’d pay out west or at big-name New England resorts.

Recommended Hotel: Hotel Vienna

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Navarre Beach, Florida; Courtesy of Zeeonenonly/Shutterstock.com

3. Navarre Beach, FL

Florida’s southernmost beaches see the biggest crowds during the winter months, when an influx of snowbirds arrive for the sun. But when you stick to a vacation elsewhere in the state, there are often better deals to be had. Dubbed “Florida’s Most Relaxing Place,” Navarre Beach is a quiet community in the Panhandle with white-sand beaches and clear-blue waters. No, it’s not going to be as balmy as Miami Beach here. But the chance of a winter snowstorm is slim to none. Area fun includes ziplining adventures with Adventures Unlimited, and there are reasonably priced beachfront hotels for bedding down.

Recommended Hotel: SpringHill Suites by Marriott Navarre Beach

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Donkey Sanctuary; Courtesy of Aruba Tourism Authority

4. Aruba, Caribbean

Families love Aruba any time of the year, and when you travel outside of spring break and other peak periods, you can usually find a decent deal on accommodations since there are so many different options on this wind-swept Caribbean isle. Treat your older kids to wind surfing lessons (Aruba has reliable breezes and is a great spot to learn) and don’t miss a visit to the Donkey Sanctuary Aruba.

Recommended Hotel: Caribbean Palm Village Resort

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Edisto Island, South Carolina; Courtesy of John Bilous/Shutterstock.com

5. Edisto Island, SC

One of our favorite family beaches in South Carolina awaits just an hour outside of Charleston in the friendly community of Edisto Island. The winter months are the off season here and the weather is hard to predict — it could be surprisingly balmy, or downright icy. Either way, there’s fun to be had in this largely non-commercialized oasis, where you can stroll the sand at Edisto Beach State Park, explore the low country’s Gullah culture, or tuck into a tasty seafood meal.

Recommended Hotel: Wyndham Ocean Ridge

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Santa Fe Plaza and Buildings; Courtesy of Tourism Santa Fe

6. Santa Fe, NM

With 300 annual days of sunshine, you can rack up some serious vitamin D when you head to the artsy city of Santa Fe for your family’s winter break. But make no mistake: Sante Fe has a four-season climate that includes an occasional light dusting of snow! Head to Ski Santa Fe, 20 miles from downtown, for affordable lift tickets and learn-to-ski packages. Santa Fe is also home to several major museums and historic sites. Many of the museums, including the Georgia O’Keeffe Museum, Museum of International Folk Art, and the Palace of the Governors at the New Mexico History Museum, offer free admission for kids 16 and under.

Recommended Hotel: Old Santa Fe Inn

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Elvis Birthplace in Tupelo, Mississippi; Courtesy of Gordon Ball LRPS/Shutterstock.com

7. Tupelo, MS

Within easy striking distance of Memphis for day trips (less than two hours away), Tupelo is an off-the-radar destination with a sweet small town vibe and plenty of fun for families in search of southern culture. Take the gang fishing on Lake Lee at Tombigbee State Park or go for an Elvis-themed bike tour (the King was born here) around town, stopping for a milkshake at Johnnie’s Drive-In. There are many inexpensive chain hotels in Tupelo.

Recommended Hotel: Hampton Inn Tupelo

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San Antonio, Texas, River Walk at Night; Courtesy of Visit San Antonio

8. San Antonio, TX 

SeaWorld San Antonio and the town’s fabulous River Walk are just a few of the reasons to plan a winter escape with your family to this friendly Texas city. The kids will love the chance to roll around the city on a double-decker bus tour or dig into a plate of authentic barbecue for lunch or dinner. The winter months usually see lots of sunshine, and even in January (the coldest month here), temperatures are still in the comfortable mid-60s. Nearly every major chain hotel in America has an outpost or two in San Antonio, which keeps lodging prices competitive.

Recommended Hotel: Drury Inn & Suites San Antonio

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Hendersonville, North Carolina; Courtesy of Alexey Rotanov/Shutterstock.com

9. Hendersonville, NC

You’re just 30 minutes from the bigger town of Asheville, North Carolina, when you stay in the nearby Blue Ridge Mountain burg of Hendersonville. Here, you’re more likely to find bargains on accommodations during winter break. Treat the kids to snow tubing at Moonshine Mountain Snow Tubing Park, said to have the steepest terrain in western North Carolina.

Recommended Hotel: The Cascades Mountain Resort

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City of Tampa Sign; Courtesy of Visit Tampa Bay

10. Tampa, FL

Basing in the city of Tampa on Florida’s Gulf Coast for a winter break is a good way to save money on accommodations while still being within striking distance of some of the most beautiful beaches in the country. You’ll be right on the city’s riverfront, within a short stroll of restaurants, museums and parks, and a quick drive to Busch Gardens Tampa Bay. And the sugar-fine beaches of St. Pete Beach, Clearwater Beach and Fort de Soto Park are all close by, too.

Recommended Hotel: Aloft Tampa Downtown

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