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The Lies You’ve Been Told About Affordable Winter Vacations

by Staff

Sometimes the biggest challenge with booking affordable winter vacations is getting over the mental hurdles that are holding you back. People tend to have misconceptions about how doable it really is to find cheap flights for winter travel. Too often, they give up before they start.  

“I probably can’t afford a winter vacation,” you’re telling yourself. “I guess I’ll just stay home and sit on the couch in my pajama pants, eating cheese dip directly out of the jar.” 

Stop that! No more negative self-talk! Don’t let the cold, gray weather turn you into a gloomy person who’s trapped in the house by inertia! Seize the moment. 

Let’s look at a few of the biggest myths about affordable winter vacations — and how you can book the trip of your dreams. 

Myth No. 1: “You’ll never find cheap international flights” 

If you want affordable winter vacations, getting cheap plane tickets is half the battle. But don’t assume that a low-price plane ticket is out of your reach — even to international destinations. 

There are great flight deal services that send cheap flight offers directly to your email inbox, like GoingTM (formerly Scott’s Cheap Flights), Dollar Flight Club, and Secret Flying. Here are a few trending flight deals we found on Secret Flying for January and February 2024 to get you out of the continental U.S.: 

  • Philadelphia to Medellín, Colombia ($276 roundtrip)
  • San Francisco to Kona, Hawaii ($189 roundtrip)
  • New York to San Juan, Puerto Rico ($141 roundtrip) 

Signing up for a few of these flight deal services can be worth a little more clutter in your inbox. And it might be worth shelling out for a paid membership if you’re super-passionate about finding cheap flights to surprising destinations. 

Want to be your own low-cost travel agent? Use Google Flights, Skyscanner, and Kayak to quickly find cheap flight deals. For example, I used Skyscanner’s flexible dates and “anywhere” search options to find these cheap flights from Denver for January 2024: 

  • Mexico flights starting at $73
  • Jamaica flights starting at $110
  • Costa Rica flights starting at $111

Don’t assume that affordable winter vacations have to happen within driving distance. You can get cheap flights to many destinations in the U.S. and other countries, if you’re flexible on dates, open-minded about connections, and eager to explore new parts of the world. 

Myth No. 2: “The only cheap hotels will be shabby and miserable” 

It’s true that if you want affordable winter vacations, you might have to compromise on lodging. You probably can’t stay at a five-star hotel with beachfront views, or the most spacious vacation rental home. But that doesn’t mean you’ll be stuck staying at a depressing roach motel with stubbed-out cigarettes sticking up out of the suspiciously stained carpet. 

You can find great hotel deals for affordable winter vacations by using popular hotel search tools like Priceline, Expedia, and Hotels.com. They let you search by location and sort by price. These search tools are perfect if you just want cheap hotels, and don’t care about earning hotel credit card reward points. 

Want an even better deal? If you love the thrill of discovery, sign up for a special offer like Priceline’s Express Deals®, where you get ultra-low prices, but won’t see the name of the hotel until after you book (and pay). Or if that feels too risky and uncertain, you can use Priceline’s Pricebreaker® feature, which shows you three possible hotels in the area with one affordable price — and you find out where you’re staying after you book and enter your credit card details.  

If this all sounds like too much work, try a new hotel deal service called HotelSlash. Just tell HotelSlash where you want to go on vacation, and it will analyze prices, sort through options, and send you an email with price quotes for the best hotel deals at your destination. A HotelSlash membership costs $29.95 per year, but if it can save you hundreds of dollars (and hours) on booking your winter vacation, it’s worth it. 

Myth No. 3: “There are no affordable winter vacations at the beach” 

If you’re longing to get away to a sunny place in the sand, you might feel like it’s too late to book a vacation at the ocean. Wrong! There are often last-minute travel offers available from travel deal search services like Travelzoo that can get you to a beachfront resort for surprisingly cheap prices. 

A quick review of Travelzoo found these great last-minute deals on winter beach vacations: 

  • Mexico (Cabo San Lucas): four nights at an all-inclusive resort (including airfare) starting at $899 
  • Dominican Republic (Punta Cana): four nights at an all-inclusive resort (including airfare) starting at $969
  • Mexico (Riviera Maya): all-inclusive resort deals for flights from Fort Lauderdale, starting at $449

You don’t have to book a beach vacation months in advance. Sometimes resorts have cancellations at the last minute, and they offer low-price deals so those empty rooms don’t go to waste. 

Bottom line: Get off the couch, put down the cheese dip, and pick up your credit card. Affordable winter vacations can be found with just a slight amount of effort. Don’t believe the myths. It’s never too late to book a fun winter trip while saving money

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