Grab a Deal on a Winter Getaway

By knowing when to travel, where to go, and other tips, you can easily find a deal on a winter getaway, from flights to lodging, entertainment, rental cars, and more.

If you go on a trip over the holidays, whether for a vacation or a family visit, you’ll usually face packed airports and elevated prices for airfare and hotels. But after the December hustle and bustle subsides, opportunities abound for cost-conscious travelers.

January and February are consistently the cheapest months of the year to fly, thanks to shrinking demand following the holiday surge. “It flips from one of the most expensive times to one of the cheapest almost overnight – around January 8,” says Scott Keyes, founder of Going (formerly Scott’s Cheap Flights), a travel company that helps people find and book inexpensive airfare. And the deals continue well into the first half of March in many places, before spring break trips begin to increase demand again, says Keyes.

Flights aren’t the only bargains you’ll find. You’ll often see lower prices on lodging, rental cars, airport parking, and entertainment and activities, such as skiing or the theater. Plus, you’ll encounter fewer crowds, which means shorter waits at airport security, better seating options on flights or trains, and more availability at the best restaurants, hotels, resorts and spas.

Bag the best bargains

To book a flight at the best price, experts typically advise that you start monitoring prices several months in advance, especially for international travel. But for trips from January through early March, you have a bit more flexibility. Generally, you can find good deals on flights anywhere from one to two months in advance for domestic travel in the early months of the year. And if you book using rewards points or frequent-flier miles, you may score a bargain even closer to your departure date. For both domestic and international flights, the sweet spot is often three to five weeks before a trip, when you are most likely to need fewer points or miles than you otherwise would for a ticket, maximizing their value, says Keyes.

Whether you’re booking with cash or points, follow the 21-day rule. Most airlines have in their policies a requirement that to get the cheapest fare, you have to book at least 21 days before your departure date, says Keyes. On day 20, the lowest fare that was available previously won’t be offered, and the new cheapest fare is going to be a bit more expensive.

Choosing your destination

Being flexible on where you go can save you a lot of money too. Rather than picking a particular destination and then looking for flights to it, consider sorting out which places come with the cheapest flights from your home airport, then choose your favorite among them. A great tool for this is Skyscanner.com’s “Explore Everywhere” feature.

Select your origin airport and either specific dates or flexible dates (with the ability to select entire months at a time) to see the best deals on flights around the world. You can also use Skyscanner to compare prices for lodging and car rentals on specific dates. Once you have a few destinations in mind, monitor prices with a tool such as Google Flights (flights.google.com) or Going.com.

But striking a balance between chasing rock-bottom bargains and settling on a destination you’re actually going to enjoy can be tricky. If none of the deals are jumping out at you, compile a list of your ideal destinations, then track flights for early 2026 to those places so you can jump on any price drops.

Suggested spots for a deal on a winter getaway

Check out these destinations. Looking for inspiration? Consider these vacation spots, which should see favorable pricing in January and February.

Florida

Whether you’re longing to relax on the beach, take in the nightlife or explore the theme parks, Florida has a little something for everyone.

Although tourists are drawn to the Sunshine State year-round, you should see significant price drops for flights, lodging and rental cars in January and February, except during the Martin Luther King, Jr. Day and Presidents’ Day holiday weekends. Early-2026 flights from Dallas to Miami, Boston to Tampa, and New York City to Miami were recently available for as little as $125, $203 and $111 round-trip, respectively, according to travel-booking app Hopper. And you can find flights to other airports around the state at a lower price than typical fares during those early months, too. Lodging for the second weekend in January recently averaged $299 per night in Miami, according to Skyscanner.

For a Florida getaway with European vibes, consider visiting Rosemary Beach, a community along Florida’s Gulf coast. Early-2026 stays at The Pearl, an independent boutique hotel, were recently available starting at $517 per night, compared with peak-season rates of as high as $850 per night. The Pearl boasts access to a private beach, a spa, and activities such as golf and kayaking.

Puerto Rico and Aruba

Caribbean locales offer U.S. travelers the perks of a tropical vacation with minimal jet lag and lots of flight options. You may find some solid post-holiday deals on flights to Puerto Rico – where U.S. citizens can travel without a passport – and Aruba. January and February are part of Aruba’s Carnival season, featuring parades and other cultural celebrations. But if you’d prefer to avoid the crowds, you can stay at one of the country’s many private resorts.

Flights from New York City to San Juan, Puerto Rico, and Oranjestad, Aruba, were recently available for as little as $220 and $369 round-trip, respectively. The cost to stay at a midrange hotel in San Juan in January starts at about $275 per night, according to Skyscanner. Typical prices per night at midrange hotels in Aruba in January are about $240, according to Google Hotels.

Europe

Late winter is possibly the most underrated season to travel to Europe. Though the weather may be cold in Europe’s northern stretches, the crowds are thinner, and the hotels and car rentals cost far less than during the holidays and the summer. And if it’s warm weather you seek, southern European countries, such as Spain and Portugal, offer a milder climate, and they should see the same price dips as many other destinations in the post-holiday travel period. Fares for early 2026 from Los Angeles to Lisbon were recently as low as $487 per round-trip ticket, according to Hopper.

If you plan to visit multiple European countries – or if an Ireland vacation is on your wish list – consider flying in and out of Dublin, using the city as your launch and return point. Flights to Dublin from major U.S. cities were recently available for as little as $350 round-trip in January and February. Stays in Dublin at a midrange hotel in January start at about $110 per night, according to Skyscanner.

Hawaii

With its striking landscapes and pristine beaches, Hawaii is a popular destination for families traveling from the West Coast during the holiday break. A sharp drop in demand following the turn of the New Year makes Hawaii a consistently reliable travel deal for those who can wait until after the holidays to venture to one of the islands, says Keyes. Early-2026 flights between Los Angeles and Honolulu were recently available starting at just $276 round-trip. Stays at midrange hotels and resorts average around $200 per night in early 2026; an early-January stay at the ‘Alohilani Resort Waikiki Beach, an upscale resort with ocean views, recently started at $251 per night.

Alternative Travel Destination to Fit Your Schedule and Your Budget

Emma Patch is a senior writer at Kiplinger Personal Finance magazine. For more on this and similar money topics, visit Kiplinger.com.

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