Surprising Stats: The Cheapest Winter Travel Destinations Revealed

Finding the cheapest winter travel destinations depends on what kind of vacation you want. Some people dream of warm-weather beaches, while others want to go skiing in the mountains.

We’re going to suggest a few surprisingly cheap winter travel options that might not be the usual destinations. Getting creative with your winter vacation can unleash great deals — and wonderful memories.

Let’s look at a few of the cheapest winter travel destinations for a variety of interests.

Winter mountain vacation: Colorado — YMCA of the Rockies

Want a winter vacation in the mountains? Consider Colorado’s YMCA of the Rockies. With locations in Estes Park and Snow Mountain Ranch, these YMCA resorts are affordable and family-friendly, with comfortable private cabins or hotel-style lodge rooms.

I have visited both YMCA Rocky Mountain resorts, and they are some of the most beautiful places I’ve ever seen. You get to wake up each morning in the midst of the Rocky Mountains — but with the convenience and comfort of on-site dining and hotel-style amenities. You can be in the wilderness without “roughing it.”

Along with mountain hikes, the YMCA of the Rockies Nordic Center offers downhill skiing, cross-country skiing, ice skating, and more. And don’t feel intimidated if you’re a newbie skier — low-cost lessons and equipment rentals are available.

How much it costs:

Lodging at YMCA of the Rockies starts at $109 a night. Flights to Denver are usually cheapest in January, according to Kayak.com.

How to get there:

Get to the YMCA of the Rockies by flying into Denver. The Estes Park resort is about 1.5 hours by car from Denver International Airport, and Snow Mountain Ranch is about a two-hour drive.

Beach vacation: San Juan, Puerto Rico

Many Americans love to go to Mexico or the Caribbean for a winter beach vacation. But what if you don’t have a passport? Try an affordable beach destination in the United States: the beautiful island of Puerto Rico!

Americans can travel to Puerto Rico without a passport because Puerto Rico is a U.S. territory. San Juan, Puerto Rico, is known for its pristine beaches, fun nightlife, and unique culinary scene with a mix of influences from African, Spanish, American, and indigenous Taíno cuisines.

Go wander the distinctive architecture of El Viejo San Juan (Old San Juan) and historic Spanish colonial forts from the 1600s. San Juan offers many fun “warm weather” activities, like rum distillery tours, snorkeling, rainforest excursions, or a nighttime guided kayak tour.

How much it costs:

We found well-rated lodging options (via Google search) a short distance from San Juan beaches in mid-January starting at around $100 per night.

How to get there:

Fly to San Juan’s Luis Muñoz Marín International Airport (SJU). Just as an example, we did a flight search using Denver as a departure city (since The Ascent has offices in Denver, and we’re always trying to curry favor with our editors by giving them free travel agent services).

According to Kayak.com, flights from Denver to San Juan are available for $250 or less during the months of January and February.

Winter city break with international flavor: Montréal

Want the feeling of visiting Europe, without the long flight? Consider Montréal, Canada! I visited Montréal for the first time in November 2022, and it’s one of the most surprising cities I’ve ever seen — fun, friendly, creative, multicultural, accessible, and affordable.

Montréal is a bilingual city where French and English are spoken everywhere. It’s a diverse international city with immigrant communities from all over the world, with restaurants serving Vietnamese, Portuguese, Greek, Indian, Italian, Mexican, and Japanese cuisines (among others). Montréal is also famous for its bagels, which I thought were world-class — although New Yorkers might disagree.

There’s so much to do in Montréal, and the public transit buses and metro trains are so efficient, you’ll barely notice the cold. My family attended a Montréal Canadiens hockey game, went to the Symphony, and visited museums. If you want to experience some of the cultural vibes of France along with some of the best of North America, go to Montréal.

(And don’t feel bad if you don’t speak French — I don’t. Just make an effort to say a few things in French, and be polite; almost everyone in Montréal also speaks fluent English.)

How much it costs:

You might not think of Canada as a winter vacation destination. But don’t let the cold scare you away! Hotels in Montréal are cheap in January; a quick Google search revealed 4-star hotels and rental apartments ranging from $90 to $125 per night.

Also keep in mind that as an American visitor to Montréal, every time you swipe your credit card, you’re paying for everything with Canadian dollars. As of December 2023, $1 Canadian is equal to $0.75 U.S. Everything you buy in Canada is going to feel surprisingly cheap! A $20 restaurant meal in Canada is “only” $14.98 in U.S. dollars. This makes Montréal an even cheaper winter travel destination — especially if you use a credit card with no foreign transaction fees.

How to get there:

Fly into Montréal-Trudeau International Airport (YUL). Flights from Denver to Montréal are around $306 in January.

Bottom line

The cheapest winter travel destinations aren’t the most-visited tourist destinations. But you can save money by avoiding the tourist mobs and getting off the beaten path. Instead of a big-name ski resort like Telluride, go to the YMCA of the Rockies. Instead of Cancún, go to San Juan (and save money on passport fees). Get away from cold weather in your home city and enjoy the cultural richness (and warm bagels and welcoming people) of Montréal.