Travel Guide: Amazing Affordable Winter Vacations

December 24, 2018 0 0

What are the best winter vacations and trips to take for travelers? If you’re looking for a great getaway, but you don’t want to wait until Spring Break to take it, rejoice, as there are all sorts of amazing affordable winter vacations to be had. All you have to do to enjoy an adventure that’s every bit as entertaining as more high-tend packages is plan your voyage a little more carefully up-front to take advantage of value-priced airfare, cost-conscious hotels, and variety of top hot spots around the world. Whether you’re seeking escape from the cold or looking to enjoy outdoor activities galore, we’ve got some suggestions to help you plan your trip. Here are ten of the best winter vacations and trips to take for travelers that are both cost-effective and sure to help you make memories on the road.




Stockholm, Sweden


Winter is the perfect time enjoy Sweden. Score flights to this Scandinavian city for under $200 one way, and luxurious hotel accommodations for as low as $120 a night. Throw in the Northern Lights, and you’ll have a magical vacation awaiting you.

Chicago, Illinois

North America

Yes, this Midwestern city does sport a windy, blustery winter, but there are hot deals on flights and hotels to be had here as well. Swing by to find a plethora of exciting, indoor activities to enjoy like ice skating, a German Christmas market, and more. The lights and displays on Michigan Avenue make it a slam-dunk holiday adventure, as do opportunities to watch the Bulls or the Blackhawks play, exquisite theaters to visit, and plenty of world-class museums to hit.

Costa Rica

Central America

With average round-trip tickets coming in at $500 from New York City to San Jose, the airfare prices are reason enough to choose Costa Rica as your tropical winter destination. What makes the prospect even better are outrageously inexpensive (under $50!) hotel accommodations. Turtle hatching and whale watching are also great wintery activities, too.



While it’s usually expensive to get to Kenya, flight deals can be had for under $1,000 in winter months. Ditto for safari expeditions. If you choose to forgo ventures, Kenya’s got some amazing beaches along the Indian Ocean.

Las Vegas,


North America

After the New Year’s been thoroughly rung in, both airfare and hotel prices drop considerably. Add to that the warm temps, the abundance of activities, and it’s easy to understand why Las Vegas is one of the best winter vacation spots to hit and trips travelers can take today.

Amsterdam, Netherlands


Imagine strolling along the snow-lined canals, with twinkling lights and warm cafés. Now, imagine experiencing this knowing you scored affordable flights and inexpensive hotel rates for your stay. The museums, the Heineken brewery, and the seasonal activities (skating rink, food festival, lights festival, etc.) make Amsterdam a more tha worthy winter destination.


North America

With Southwest Airlines entering the Hawaii market, airfares to these idyllic islands should trend downward. Especially look to travel in February when fares typically are their lowest and keep an eye out for special sales. Then head to the beach or a boat for whale watching to catch a winter tan.

Cheyenne, Wyoming

North America

Instead of downhill skiing in Vail or Aspen, try cross-country activities, ice boating, or ice fishing in Cheyenne. Located less than two hours outside of Denver, this gorgeous little city boasts some fantastic outdoor activities, without the crowds or expense.

Madeira, Portugal


These four semi-tropical islands — where Madeira Port is made — are just a short (and less than a $40) flight from Lisbon, and flights to Lisbon are reasonable, too. Add to that, low hotel costs, and the affordable vacation comes together. While it might be too cool to sunbathe on the beaches, it’s still warm enough to wander through gardens, explore castles, and play a great game of golf.

Dubai,United Arab Emirates

Middle East

It’s cheaper to visit Dubai in the winter. Even though the temps may be cooler where you live, here, it’s a balmy 70 to 80 degrees, and the beaches, of course, are gorgeous. February is also the cheapest time to fly.

Cheat Sheet

It’s easy to be a snowbird when you know where to go. You can find more on the best winter vacations and trips to take for travelers when you read about the destinations below.

Tags: Culture, Travel Categories: Culture, Travel
Jeanette Hurt

Jeanette Hurt is the award-winning writer and author of eight culinary and drink books, including The Cheeses of California: A Culinary Travel Guide, which received the 2010 Mark Twain Award for Best Travel Book, and The Complete Idiot’s Guide to Wine and Food Pairing. She's written for, Four Seasons Magazine, Wine Enthusiast,, and dozens more publications.

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