Little Boys Sipping Hot Cocoa; Courtesy of mamaza/
All Ages

12 Ridiculously Affordable Winter Vacations 2019/2020

Terry Ward is based in Florida and has worked as a freelance travel writer since 2000, writing for such publications as CNN, Conde Nast Traveler, National Geographic, The Washington Post and Scuba Diving Magazine, among many others. She lives in Tampa with her two young children and husband and has traveled with them to the Arctic, Cuba, Morocco and elsewhere. Her favorite family travel destinations are Norway and Florida. See more of her work at

See recent posts by Terry Ward

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 cheap winter family vacation.

Aerial View of Cancun; Courtesy of harvard1932/

1. Cancun, Mexico 

With so many hotels, resorts, guest houses and family inns to choose from, greater Cancun makes for a popular and cheap winter family vacation 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!) 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

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 cheap winter family vacation 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.

Recommended Hotel: Hotel Vienna

Navarre Beach, Florida; Courtesy of Zeeonenonly/

3. Navarre, 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. Bonus: Navarre Beach was named of the 10 Best Beaches for Families in 2019.

Recommended Hotel: Springhill Suites by Marriott Navarre Beach

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

Edisto Island, South Carolina; Courtesy of John Bilous/

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

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

Elvis Presley Birthplace; Courtesy of Visit Tupelo

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, making it ideal for a cheap winter family vacation.

Recommended Hotel: Hampton Inn Tupelo

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

Downtown Hendersonville, North Carolina; Courtesy of Henderson County Tourism Development Authority.

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: Cascades Mountain Resort

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

Nassau, Bahamas

11. Nassau, Bahamas 

There are plenty of deals to be found in the Bahamas right now, and following Hurricane Dorian, tourism to the Bahamas is vital to its recovery. Nassau, which wasn’t impacted by the hurricane, is the perfect destination for an affordable tropical winter vacation with the kids. When you’re not on the beach or swimming in your resort pool (or better yet, playing at Aquaventure at Atlantis), visit the Pirates of Nassau Museum or do some shopping at the Straw Market.

Recommended Hotel: Comfort Suites Paradise Island

Related: Free (or Cheap) Cruise Shore Excursions in Nassau, Bahamas

Chicago Skydeck, Courtesy of Choose Chicago

12. Chicago, IL

Chicago winters are downright cold, and less people visit the Windy City at this time—which means hotel pricing is competitive and there are more deals to be found! Brave the cold for ice skating at a number of free-admission rinks; sledding near Lake Michigan; and the polar bears and snow monkeys during ZooLights at the free-admission Lincoln Park Zoo. When the kiddos are ready to warm up, head to the indoor gardens at the Garfield Park Conservatory or sip on hot cocoa at Bombobar, where options include Funfetti hot chocolate! Don’t miss a visit to the Chicago Skydeck at Willis Tower, either.

Recommended Hotel: Embassy Suites by Hilton Chicago Downtown

Longtime travel writer and adventurer Terry Ward lives in Florida with her husband and young son and daughter. She’s constantly on the lookout for the next Scandinavia Airlines Kids Fly Free deal to save money on flights to Norway, her favorite place to visit both in the winter (Northern Lights!) and summer (Midnight Sun!). A travel writer since 2001 (read: long before the kids came along), she’s written for such publications as Endless Vacation Magazine, Conde Nast Traveler and Scuba Diving Magazine, among many others. Find Terry on her website,

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