Lock In Your Holiday Travel Now

Quick check in: if I asked you right now where your family is spending Thanksgiving or the December holidays, could you answer?

If not, you're running out of time. September is when travel insiders quietly lock in both the where to go and the where to stay, before Halloween decorations go up and the best destinations, rooms, and rates for the season disappear.

Below, we've grouped this year's best holiday trips by the kind of holiday season your family is actually after - mountain magic, warm-weather escape, classic city lights, or full European storybook mode - with a stay-worthy hotel pick for each one.

🏔️ If Your Family Wants a Snow-Globe Christmas: Vail, Colorado

Vail leans hard into its Bavarian-village bones every December with outdoor ice skating, a town-wide tree lighting, and weekend "Smile with Santa" meet-and-greets that make the whole town feel like a movie set.

Stay at: Sonnenalp Hotel. Set right in Vail Village, Sonnenalp gives you that "Europe in the winter without the flight" feeling, decked out top to bottom for the season and walkable to shops, restaurants, and the ski lifts.

🏖️ If Your Family Wants Christmas Without the Cold: San Diego, California

You don't have to trade holiday magic for warm weather. San Diego pulls off both. Think beachfront ice skating, twinkling light displays, and a Victorian-style festive afternoon tea, all with the Pacific Ocean as your backdrop.

Stay at: Hotel del Coronado. The Del does Christmas in a way that still feels distinctly San Diego with beachside igloos, gingerbread houses, holiday movie nights on the sand, and ice skating steps from the water.

🏙️ If Your Family Wants Big-City Lights: Chicago, Illinois

Few cities lean into the season quite like Chicago. Ice skating and caroling at Millennium Park, the genuinely authentic Christkindlmarket at Daley Plaza, 750,000 lights at the Chicago Botanic Garden's Lightscape, and the Museum of Science and Industry's Christmas Around the World exhibit means this is a city built for a family holiday checklist.

Explore our full guide: we've mapped out 12 of the best holiday events in the city, plus where to actually stay.

​See Our Favorite Chicago Holiday Events → Find Our Favorite Chicago Family Hotels →​

🗽 If Your Family Wants the Classic Christmas-Movie Trip: New York City

There's a reason NYC holiday trips are a rite of passage with the decorated windows, the Rockefeller tree, and the sheer scale of it all.

Stay at: The Plaza. Follow in Kevin McCallister's footsteps with the hotel's Home Alone-inspired family package, then round out the trip with a Christmas Eve dinner in the Palm Court and a festive afternoon tea. It's the kind of stay that becomes the story your kids tell for years.

🎄 If Your Family Wants to Go All-In: Germany's Christmas Markets

If you're dreaming bigger this year, nothing beats the real thing. Germany's Christmas markets date back to the 15th century, and cities like Nuremberg run dedicated children's markets (complete with carousels, hands-on gingerbread building, candle-making) alongside the mulled wine and wooden ornament stalls adults come for.

Planning a multi-city Christmas market trip with kids is a genuinely big undertaking - routes, hotels, which markets are actually worth the crowds. We put together a complete 10-day itinerary covering Heidelberg, Munich, Nuremberg, and Rothenburg ob der Tauber, built specifically around traveling with family.

​Get the Germany Christmas Markets Family Travel Guide →​

More Hotels Worth Building a Trip Around

Beyond the five above, a few more from our full roundup are already showing limited December availability:

• ​The Broadmoor (Colorado Springs, CO) - twelve straight days of holiday programming, anchored by a real, edible, life-sized gingerbread display.
• Gaylord Hotels (Nashville, Dallas, Orlando, Denver, DC, San Diego)- home to the famous "ICE!" experience, a walk-through world built entirely from two million pounds of hand-carved ice, kept at a brisk 9 degrees so bundle up. Every property has its own theme and holiday programming, so pick whichever city fits your trip.
• ​Omni Mount Washington (Bretton Woods, NH) - sleigh rides, ice tubing, and a packed Christmas in the Mountains schedule every Friday through Sunday.
• The Greenbrier (White Sulphur Springs, WV) - the literal filming location of its own Christmas movie, with a dedicated Christmas shop and weekend Santa visits.

​See the Full List of 25 Best Christmas Hotels for Families →​

Let me know if I can help with creating some holiday magic for your family! Just hit REPLY!

Kirsten