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Best Affordable Winter Getaways

Written by Chris Osburn

This blog post was updated on May 15, 2020.

Already planning your great winter getaway? Whether you’re a snowbird seeking to avoid the cold or a ski bunny hoping to make the most of it, our list of affordable destinations for the holiday months is full of great places that can either warm you up or keep you cool. So what are you waiting for? Start looking for some cheap flight deals and pack your bags!



Don’t be a jerk, mon! You could be jammin’ the winter blues away in the Caribbean sun to some excellent reggae on the beach! There’s a wide variety of options for visitors to this sunny island. All-inclusive packages are some of the best priced in the Caribbean. For those inclined to self-catering, Jamaica can be a super cheap destination as well.

Looking for cheap flight deals for your winter getaway? Check out these limited-time fares that can get you there for less!

Las Vegas


After New Year’s Eve, the rates go down for Las Vegas flights and hotels, but the temperatures still stay warm with plenty to see and do. And while it’s hot in town, there’s skiing in the mountains not so far away. Remember “Nevada” means snowy in Spanish.



The peso is at the lowest exchange rate against the dollar at the moment, making your dream vacation to Mexico an even bigger bargain than usual. However much you save on your trip, you’re sure to return home with priceless memories of white sand beaches, amazing food, and incredible cultural experiences.

New Orleans


Image via Flickr CC – Lars Plougmann

Very affordable, usually warm, and always fun – New Orleans is a super winter destination for music fans, foodies, and anyone looking for a good time. Visitor numbers swell during New Year’s Eve and Mardi Gras. During the rest of winter though, there’s plenty of elbow room.

Quebec City


For those keen to fully embrace the brrr, Quebec City’s Winter Carnival (aka the Carnaval de Québec) brings icy fun to this beautiful Canadian city in one of the biggest and best-loved winter festivals in the world.

St Simons Island


The biggest of Georgia’s Golden Isles, St Simons Island is an outdoor lover’s paradise. The island’s year-round mild climate means you can make the most of its broad sandy beaches, world-class golf courses, and historic sites when you head down that way.

RELATED: South America is the perfect destination for a budget-friendly winter escape. Find out more about The Cheapest Countries You Should Visit in Central and South America!

San Diego


San Diego is an awesome place to visit any time of year, with plenty of attractions, beaches and, of course, its famously fabulous blue skies and warm weather.

San Juan, Puerto Rico


Winter is a time to sizzle in one of the oldest cities in the Americas. For some of the Caribbean’s best-preserved historical sites, cool cocktails, hot dancing, and a variety of fun-in-the-sun activities, San Juan is a sensational place to be.



If picturesque mountains, powder-white snow, and exhilarating winter sports are more your thing, then Vermont is the place to go. The state has slopes in places like Stratton and Mad River Glen that offer some of the best skiing on the East Coast – and at very reasonable rates.

If you’re thinking about that winter trip to bring you some much-needed rest and relaxation, then just start planning your trip by selecting a great location from this list and looking for some cheap flight deals!

Where would you like to travel this winter? We would love to hear about your favorite places to make the most of cold weather as well as those places to go to avoid it altogether.

About the author

Chris Osburn

Chris Osburn is a freelance writer, photographer, consultant, and curator and the driving force behind the long running and award winning blog, Originally from the American Deep South, Chris has lived and worked all over the world and has called London home since 2001.

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