How to Plan a Winter Vacation That’s Cheap and Memorable

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Want an affordable winter vacation? It’s not too late! But you might need to be creative and embrace the cold. Learn how to find a cheap, fun winter vacation. 

Want to get away during the gloomy months of winter? Planning a winter vacation can help you recharge and refresh during the cold, dark times of the year. But going on a winter vacation doesn’t have to wreck your budget.

Let’s take a look at a few ideas for how to plan a winter vacation that can give you fantastic travel experiences at an affordable price.

Choose a cold weather city

When most people plan a winter vacation, they want to go to a warm-weather destination like Florida, California, or Mexico. Lots of people want to go to the beach, or Disney World, or other sunny destinations. But because everyone wants to go somewhere warm in winter, airfares, hotels, and tourist experiences get much more expensive.

You can save big money on your winter vacation by embracing the cold! Go to a snowy city — though probably not a ski resort, because those places also get crowded and expensive during winter. But a fun city with great restaurants, live music, and culture can be a perfect winter destination.

Last year, my family and I took a winter vacation to Montréal, Canada. The flights were cheap, and we got a great deal on our Airbnb and restaurant meals because the U.S. dollar was so strong against the Canadian dollar. And we loved Montréal!

The weather in Canada was not much colder or darker than what we would’ve experienced at home in the American Midwest, and we had a marvelous time exploring a fascinating, multilingual, international city. We ate great Vietnamese fusion food and bagels and poutine, we watched a Montréal Canadiens hockey game, we visited museums and went to the Symphony. Even though the weather was cold and the sun went down early, this was one of the happiest vacations we’ve ever had.

Remember: Even if you’re on winter vacation in a cold weather city, you can spend most of your time indoors, enjoying delicious food and warm beverages.

Visit a rural area or small town

America is full of less-visited places in small towns and rural areas that are often overlooked by tourists. What if you could plan a winter vacation to get you off the beaten path? Here are a few ideas for winter vacations in rural America:

State parks: Many state parks offer cabin rentals and winter activities like hiking, cross-country skiing or snowshoeing. Nearby hotels or Airbnbs are likely to be much cheaper than you’d pay in a big city (or at a crowded national park).Unique country lodging: What if you could stay at a rustic cabin in a forest, or a mountain chalet, or a riverside cottage? There are many ways to have a fun experience closer to nature, while still having modern comforts like wifi.Farmstays: Have you ever wanted to experience life on a farm? Try doing an agritourism farmstay, where you can wake up in the countryside, help feed farm animals, and experience farm-to-table cuisine.Small town tourism: There are many small towns like Galena, Illinois (a popular weekend destination for people in my home state) that offer historic buildings, great restaurants, fun shopping experiences, and friendly people who would love to share their communities with you.

Don’t assume that great winter vacations can only be found in the usual beachfront destinations or big cities. You can have a wonderful winter vacation at lots of different points on the map if you’re willing to be curious and open-minded.

Use search tools to find “anywhere” travel ideas

Don’t know where you want to go for your vacation? Want to find the best possible travel deals, even for places you’ve never heard of? If you’re flexible and want to find an affordable winter vacation, check out these travel search tools. You can use these search tools to search for “Anywhere,” without a specific destination:

Airbnb: In the search box for “Where/Search destinations,” you can click “I’m flexible” to see a wide range of locations and lodging options. You can also choose unique accommodations, like cabins, tree houses, farms, boats, and “OMG!” which offer truly one-of-a-kind places to stay, like a Conestoga Wagon “glamping” resort, or a refurbished 1920s gas station.Google Flights: In the search box where it says “Where to,” you can click “Anywhere” and see a wide range of airfares for trips all over the world. This is a great way to get ideas for new places to visit on your winter vacation, and you might even find some surprisingly cheap airfares.Kayak: This travel site lets you click “Explore” to find the best winter vacation travel deals. Start by entering your home city’s airport, and then choosing a month of the year when you want to travel. Kayak will quickly show you a wide range of affordable airfares to multiple destinations. You can also choose the types of winter vacation you want to take, like “Beach,” “City,” “Family,” “Outdoorsy,” and more.

Use travel credit cards for rewards and special offers

If you want to save money on a winter vacation and get special travel experiences, you might want to consider applying for a new travel credit card. The best travel credit cards offer generous sign-up bonuses, such as 75,000 frequent flyer miles or 60,000 bonus points, that can help make your winter vacation more affordable.

Especially if your winter vacation involves booking international flights and several nights of lodging for your family, getting a travel credit card or airline credit card could be a good idea. Paying for a big winter vacation with an airline credit card can help you get elite airline status. Maybe you’ll get so many reward points or bonus miles that your winter vacation will help pay for itself!

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