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Where to Find Great Deals on Winter Vacations

Barbara Kiviat

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While beach vacations in the Caribbean and ski trips to the Rockies are costly this time of year, there are plenty of good deals available to less sought-after destinations such as big cities in the U.S., some colder regions of the country, and out-of-the way locales. 

Jared Kamrowski, who runs the website, says he and his wife have a number of trips planned over the next few months, including visits to Chicago and Fargo, North Dakota.

"Airfares and hotel prices can be much more expensive during the summer than in the winter, so we're going now," says Kamrowski.

January is actually the cheapest month to fly as domestic airfare prices are 31 percent lower on average than peak prices during the summer, according to the airfare-tracking app Hipmunk. Some of those deals could spill over into February and early March.

Hotels and vacation rentals also offer big discounts in the winter, with prices in some markets dropping by as much as 42 percent compared to the fall, according to TripAdvisor Rentals

If you're looking for an affordable midwinter getaway, here are four ideas.

Off-Season Resorts

While the peak season to go to Myrtle Beach, S.C., is from March to September, you'll find lower prices in January and February. Temperatures during the early winter months are still comfortable—they reach into the 50s and 60s—so you can still play golf. Another benefit: You’ll probably be able to grab a tee time, and get a discount.

Airfares to Myrtle Beach are 17 percent lower on average than during high season, according to airfare-tracker Hopper. While there, you can visit the shops, boardwalk, aquarium, and SkyWheel, which are all open year-round. Even if it’s too chilly for a dip, you still have beautiful views of the ocean.

Another big upside: In winter, lodging prices take a dive. Rates on vacation rentals cost half of what they do during the summer, according to TripAdvisor Rentals.

It might take a little more ingenuity to enjoy a more northern beach resort in winter, says Pauline Frommer, editorial director of Frommer’s guidebooks. She recommends the Massachusetts shore, including Nantucket, for walks on the beach, sightseeing in quaint towns, and great dining. (On Nantucket, The Sea Grille and Bartlett’s Farms are among the spots open year-round.) Rental houses on the island are also half-price.

Many historic sites and museums are seasonal, but others are open in the winter. Nantucket's Whaling Museum, for example, opens in February.

Classic Beach Vacations

If warmer weather is a must, there are still some good options.

Winter flights to Florida cities such as Miami, West Palm Beach, Orlando, and Fort Myers can be surprisingly reasonable. According to Hopper, ticket prices are up to 20 percent cheaper on average than during the summer.

Kamrowski says there are also good deals to places that travelers have shunned due to negative news. He recommends considering San Juan, Puerto Rico—prices are lower because many people stopped traveling there after Hurricane Maria hit in 2017.

Another option: the beaches of Mexico. Kamrowski says that while many are safe, prices are low partly because travelers are concerned about violence from drug gangs. A bomb that detonated last February on a ferry that travels between Playa del Carmen and the island of Cozumel didn't help.

For the best lodging deals, look off the beaten path. Vacation houses in Destin, on the Gulf Coast in Florida’s panhandle, rent for up to 60 percent less than they do during the high season, which begins in April, according to the vacation rental site HomeAway.

But there's a crucial caveat: Get in and out of Florida before spring break kicks into high gear around the second week of March.

For West Coasters, San Diego is a great nearby winter destination. The hotels there have some big discounts now, with rates 20 percent lower than during summer, according to Travelocity data.

Winter is also prime whale-watching season in San Diego, when gray whales migrate past Point Loma and Cabrillo National Monument. While the water may be too cold for swimming, it’s a beautiful time of year to explore Balboa Park, the San Diego Zoo, and the historic Gaslamp Quarter with a fraction of the crowds.

Big Cities

Heading to a major city in the winter can often be less expensive than during the summer, says Patrick Surry, chief data scientist at Hopper.

Flights to Chicago (shown at top) this winter cost almost 30 percent less on average than they did in high summer, according to Hopper data, and flights to New York City are discounted almost 20 percent.

There are also good winter deals on lodging in many cities. According to the booking site Travelocity, hotels are offering discounts of 20 percent to 30 percent from their summer rates in destinations such as Boston; Chicago; Portland, Ore.; San Francisco; and Seattle.

Of course, it’s never difficult to find plenty to do in these great American cities, though winter does bring some seasonal  opportunities, like outdoor ice skating with skyline views on Frog Pond in Boston and in Millennium Park in Chicago.

If New York is a city you'd like to visit, you can be among the first to see new Broadway plays that open during the winter months. This year, the list of winter openings includes revivals of "Kiss Me, Kate" and "True West." 

For nature lovers, the Stanwood-Camano & Birding Festival takes place in late February an hour north of Seattle, with tours of the wintering grounds of birds that come from as far away as Alaska and Russia.

Our Neighbor to the North

Canada may not be a top-of-mind destination in the winter months, but with the strong U.S. dollar, Canada is essentially 30 percent off, Frommer says. That makes it a pretty good winter destination.

While there’s no way around the cold, Montreal offers plenty of indoor diversions like its world-class Museum of Fine Arts, which opened a new wing in late 2016, and has a special exhibit called Thierry Mugler: Couturissime beginning March 2. The exhibit covers the work of the French couturier, director, photographer, and perfumer.

If you don't mind venturing outside, you could attend Montréal en Lumière, a festival that runs from Feb. 21 to March 3 with concerts, food, and must-see art installations.

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