The winter holiday season is the most magical time of the year! The air begins to smell like cinnamon. Mugs of hot chocolate become a pantry staple, and ordinary city blocks turn into fantastical winter wonderlands under festive strings of lights.
While it’s tempting to stay home and curl up next to the fireplace, you’ll miss out on all the festive fun.
Here’s my guide to the best markets and festive hotels to help you plan the best winter holiday getaway with none of the stress!
When to Book Your Festive December Vacation
Want to avoid high prices for your holiday travel? Get your logistics out of the way as soon as possible.
Look for early booking discounts, package deals, and off-peak promotions to save money and make planning easier.
Flying and staying for a first-week-of-December trip works well when you book by early October. Planning a trip for mid-December lands best if you book by late September. Traveling during the peak window around Christmas and New Year’s gets easier (and more affordable) if you book by early September.
Next, avoid weekend dates (if you can).
A stay that runs Sunday to Thursday can cost less than the same number of nights over a Friday and Saturday.
Lastly, lock in a hotel with a free cancellation policy. Then, two to three weeks before you go, check whether rates have dropped. If it’s a yes, cancel, and rebook your stay.
The Best Winter Wonderland Destinations in the USA
New York City
New York City is one of the best winter holiday destinations in the USA. You have the Rockefeller Center Christmas Tree, holiday shows like the Rockettes at Radio City, and the classic NYC Ballet’s Nutcracker performance.
…But the real star of the show? The Bryant Park Winter Village.
It’s open long enough for those who like to get their Christmas shopping out of the way and late enough for all of us who leave gifting to the last possible second.
Want to avoid the crowds as much as possible? Plan your visit for a weekday evening. After shopping, grab some dinner at one of the food stalls and end the day with a skate around the ice rink.
It’s quintessential NYC holiday magic!
Chicago
Chicago in December is the chilly winter wonderland vibe you’re searching for. Come here for the big-city glow of Michigan Avenue, the glittering Christmas tree at Millennium Park, and festive indoor escapes like the Art Institute when the wind gets aggressive.
…And your Christmas shopping?
It doesn’t get better than spending a few hours at Christkindlmarket.
If you can, plan your visit for an early afternoon on a weekday and come hungry! My favorites include the roasted nuts, warm butter pretzels, and of course, the delicious hot spiced wine!
After the market, pair it with a loop around Chicago to see the lights, and always add one museum or show as a cold-weather buffer in case the weather doesn’t play along.
San Francisco
San Francisco won’t give you blizzards and a snow day, but it still delivers the festive cheer in spades.
My go-to?
The Union Square Ice Rink.
Open from November to January, it’s daily hours stretch as late as 11:00 pm, and I love it! Late at night, skating feels romantic, like I’m in one of those cheesy Netflix holiday romcoms.
But what I love more are the theme nights.
Drag on Ice is a personal favourite! As well as Silent Skate (think silent disco vibes) and Polar Bear Skate on New Year’s Day, it’s always a good time. Come in your most outrageous swimwear and see if you can snag a best-dressed prize!
Québec City
Québec City in winter feels like stepping into another era. Come for the snow-dusted stone streets of Old Québec, the warm glow of café windows and lantern-lit lanes, and the German Christmas Market that turns the historic core into a storybook scene.
Open to the public from November 20 to December 23, the market brings a little slice of Europe to Old Québec, with wooden stalls selling ornaments and handmade gifts, plenty of seasonal snacks, and warm drinks that keep you lingering even when the temperature drops.
If you do make your way here for Christmas, pack the right footwear and winter essentials! Be prepared for icy sidewalks and snowy roads to stay safe and comfortable during your visit.
The Best Holiday Hotels for a Festive Getaway
Some hotels produce an entire holiday season. Add one to your itinerary and get into the festive spirit!
The Plaza (New York City)
The Plaza deserves a spot on any Christmas lover’s wishlist. Aside from the gorgeous holiday decor, you can indulge in a Christmas Day afternoon tea at The Palm Court and attend the hotel’s magnificent tree-lighting ceremony.
Top Tip: Stay one night at The Plaza for access and atmosphere, then shift to a more midrange property nearby for the rest of the trip.
Fairmont Le Château Frontenac (Québec City)
Fairmont Le Château Frontenac is Québec City’s holiday crown jewel. The castle-like silhouette looks fantastical in the snow, and the festive decor inside makes it feel like you’re staying in a storybook rather than a hotel.
Its Old Québec location means you can walk to the German Christmas Market, pop back to warm up, then head out again when the lights come on.
Top Tip: Book a room with river or Old Town views.
Hotel del Coronado (San Diego)
Hotel del Coronado gives you holiday energy, but instead of snow, you have the beach. The historic beachfront setting is iconic year-round, but December is when it really commits to the bit. Book a stay here for oceanfront lights, festive pop-ups, and the magical Skating by the Sea rink.
The Broadmoor (Colorado Springs)
A holiday stay at The Broadmoor is all about grand decor, glowing grounds, and a festive program full of entertainment without leaving the property. It’s perfect for when the weather turns, and you don’t want to stay cooped up in your hotel room.
Top Tip: Book a midweek stay for better rates and fewer crowds.
Get Ready for The Holiday Travel Season
Holiday trips can feel indulgent on paper. Flights cost more. Hotels charge a premium for the same room.
…You might even wonder, “Is this all worth it?”
Then you’re standing in the cold holding a mug of mulled wine. You’re listening to Mariah Carey’s “All I Want for Christmas” anthem, and spending quality time with your dearest while feasting on festive delights.
What’s your favourite winter wonderland destination in North America? Let me know in the comments below!