Insanely Affordable Winter Vacations in 2020

united states

If you haven’t taken a look at my website quarterly story on the cheapest places to fly right now, you should. But getting a cheap flight only puts you halfway toward an affordable trip.

In that spirit, here are nine affordable winter vacation destinations that typically offer both cheap flights and good on-the-ground prices; plus plenty of fun activities and sights.



According to some sources Las Vegas has historically been one of the cheapest places to fly in winter, with median airfares of about $200 round-trip.

Or head to Reno-Tahoe for about $300 round-trip from most major U.S. cities. Nevada is an affordable winter vacation spot that sees mild weather and offers a variety of activities, from casino-hopping to outdoor activities like hiking and skiing.

Where to Stay:

Peppermill Resort offers prices as low as $100 per night in the winter, and it has geothermally heated outdoor pools that are open year-round.

The Peppermill and other resorts in the area also offer ski packages to Tahoe ski resorts like Mt. Rose and Diamond Peak, packages that include accommodations, shuttle service, ski rentals, and lift tickets.

Asheville, North Carolina


With budget airlines recently expanding to this city in the Blue Ridge Mountains, Asheville has historically seen a 40 percent drop in winter airfares, according to CheapOair.

Walk around the hip city’s Art Deco downtown area, take a rooftop bar tour for amazing views, drink up at some of the city’s 33 breweries in the South Slope District, or even take a wintertime hike (here are five to choose from).

Where to Stay: 

The Cambria Hotel & Suites Downtown Asheville has a great location and options for larger groups. Winter rates are typically cheapest, and you can walk to 88 nearby attractions including award-winning restaurants and shops.

South America


Thanks to expanded LATAM routes and the airline’s new partnership with Delta, convenient and cheaper flights to South America are more readily available across the United States.

Check out affordable Sao Paulo, head to Rio de Janeiro for Carnival season—flights have historically been 24 percent cheaper in winter—or check off a bucket-list destination like Patagonia, Bolivia’s Salt Flats, or the Inca Trail.

How to Visit: To ease your trip planning, book a group travel tour with an operator like Intrepid or G Adventures. Both companies offer Black Friday and Cyber Monday deals each year, which gives you even more of an excuse to go in winter. After all, this time of year is summer in South America.

Warsaw, Poland


Poland’s cities are among the cheapest to travel to in winter, with prices historically averaging about $580 round-trip from the United States, according to CheapOair.

Whether you’re looking to celebrate the holidays in Europe or experience a world-class European city on the cheap, the capital of Warsaw should be on the top of your list.

Classic wintertime activities include ice skating in Old Town Square, strolling through the city’s outdoor illumination exhibit, visiting the Royal Garden of Light, and soaking in the outdoor heated pools at Wodny Park.

Where to Stay: The trendy H15 Boutique Hotel has rates starting around $130 per night and will put you right in the city center. Large rooms and apartment options make this a great location for groups or family stays, and guests love the breakfast and room design.

Atlanta, Georgia

Insanely Affordable Winter Vacations

Atlanta is often one of the cheapest warm locales to visit during North America’s winter, with flights as low as $100 round-trip from major U.S. cities.

Enjoy the milder temperatures at outdoor parks including Centennial Olympic Park and the Botanical Garden; stroll neighborhoods like Little Five Points and Cabbagetown, and discover the emerging culinary scene at James-Beard-caliber restaurants.

You can also volunteer on Martin Luther King Jr. Day in the hero’s birthplace, and see the city light up for the holiday at the Callaway Gardens, Lake Lanier Islands, or Lenox Square.

Where to Stay: Nightly rates for the Hyatt House Atlanta/Downtown start around $120 per night in the winter. The hotel is conveniently located within walking distance to the aquarium, Centennial Olympic Park, CNN Center, and The World of Coca-Cola.

Also like 10 Places to Visit In New York City In 2020/

Southeast Asia


Laos and Cambodia have seen lower airfares in recent winter seasons, with round-trip prices dipping well below $1,000 to cities like Siem Reap. Service to destinations like Ho Chi Minh City (Vietnam) and Phnom Penh (Cambodia) via Bangkok has also expanded, so you can maximize your travel options.

The warm and dry high season in the region stretches from January to March, meaning you don’t have to worry about monsoons or other weather threats during this time of year.

How to Visit: Discover everything the region has to offer with group travel company Intrepid’s nine-day Cambodian Traveler trip, which starts at just $880; or the 11-day Essential Vietnam trip, from $740.

Seattle, Washington


Getting to Seattle in winter is inexpensive compared to the rest of the year, with airfare prices in the winter months as low as $250 round-trip from East Coast locales like Boston and Baltimore, according to some other websites. Free holiday events include family and shopping activities at Pike Place as well as Seattle Center Winterfest.

Where to Stay: The Moore Hotel, near Pioneer Square, is around $130 per night. Guests love the location and convenience of the attached restaurant, bar, and coffee shop, plus there’s a working, vintage theater in the same building that adds to its historical ambiance.

Flagstaff, Arizona


Snowbirds flock to Arizona as cold weather hits, and while many heads to the Phoenix area for warmer weather, nearby Flagstaff delivers a pretty convincing winter experience, with averages of 100 inches of snow annually in the downtown area.

Airfarewatchdog says fares dip as low as $300 round-trip for winter months from departure cities like Boston, Atlanta, Austin, and Chicago.

Winter hiking, brewery hopping, skiing, snowmobiling, stargazing not to mention its accessibility to the Grand Canyon about 80 miles away are all great reasons to explore this lesser-known destination.

To boot, winter is more affordable and the Grand Canyon is less crowded. Plus, there are very few places in the world where you can see snow contrasting with the area’s famous red rocks.

Where to Stay: The Weatherford is a historic hotel right in downtown offering winter rates that start around $115 per night. It’s a little quirky, friendly, and fun, with an attached pub and Wild-West feel.

Also read our article on 10 Unique Islands To Visit In 2020



Boston, Chicago, Baltimore, and other North American departures cities see regular price drops on flights to Vienna during the colder months, making this popular skiing country in Europe a great affordable winter vacation.

How to Go: Hit the slopes in the Austrian Alps with tour operator Contiki on the Austria Ski package, a week-long ski trip starting at $430 (including accommodations, day trips, and most meals).

Based in Hopfgarten, it’s the perfect base to explore the SkiWelt, Austria’s interconnected ski slope network. The country embraces cold weather with famous Christmas Markets, ice skating rinks, roasted chestnut, and potato wedge stalls, mulled wine, and its best opera season.


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