5 Winter Ski Destinations You'll Want on your Radar
Ready to start planning your next winter getaway? Kim Lalande, founder and CEO of Key.co, joins us to share five of her favorite ski destinations, including Telluride, Park City, Big Sky, Breckenridge, and North Lake Tahoe. We’re talking beautiful vacation rentals, ski-in/ski-out access, hot tubs, private chefs, and the little details that can make a winter vacation truly relaxing. From cozy mountain cabins to unforgettable ski days, this episode will have you ready to book your next winter adventure.
When the temperatures are still warm and summer is in full swing, winter can feel very far away. But if you’re dreaming about snowy mountains, cozy cabins, hot tubs, and days spent skiing, now is actually a great time to start planning!
What to Look for in a Ski Vacation Rental
Before getting into the destinations, Kim shared some of the things travelers should keep in mind when choosing a vacation rental for a winter getaway.
Ski trips often include families, couples traveling together, friends, or even multiple generations of a family. Having the right home can make a huge difference in how enjoyable the trip is.
Here are some of the features Kim recommends looking for:
A great gathering space: Look for a large living room where everyone can relax together after a day on the slopes.
Mountain views: There’s nothing better than waking up to a snowy mountain view.
A fireplace: Perfect for morning coffee, an afternoon break from skiing, or winding down at night.
Ensuite bedrooms and bathrooms: Especially important when traveling with multiple couples or generations of family.
A private hot tub: One of the ultimate ski trip luxuries, especially when you can enjoy it while taking in the mountain views.
Ski-in, ski-out access: This makes it much easier for everyone to come and go on their own schedule without coordinating rides.
A ski room or mudroom: A dedicated space for snowy boots, skis, and gear keeps the rest of the house much more comfortable.
Kim also recommends taking advantage of services that make a ski vacation easier, like ski valet, where equipment can be delivered directly to your vacation rental, fitted there, and picked up when you leave.
And if you're hiring a private chef, Kim has a great tip: ask them to prepare an extra heat-and-serve meal while they're already cooking. That way, you have an easy breakfast or lunch ready for the next day without having to cook.
1. Telluride, Colorado
Telluride is one of Kim's favorite destinations, and it's easy to see why.
It takes a little more effort to get to than some of the other destinations on this list, but that is also part of its charm. The extra distance means Telluride doesn't feel quite as crowded or overrun as some other popular ski towns.
The town itself has plenty of character, with great restaurants and shops to explore. If you stay in Mountain Village, you can take the gondola down into the town of Telluride for dinner and then ride it back up afterward.
A few things Kim loves about Telluride:
Charming, character-filled town
Great restaurants and shopping
Gondola connecting Mountain Village and Telluride
Beautiful vacation rental options
Less crowded feel than some larger ski destinations
Great hiking and waterfalls in the summer too
Getting There
Most travelers fly into Montrose, followed by roughly an hour-and-a-half drive to Telluride. There is a smaller airport closer to town, but flights can be more weather-dependent.
Because of the extra travel time, Kim recommends Telluride for a longer trip, especially if you're staying five days or more.
And if you're looking for a winter destination that is just as beautiful in the summer, put Telluride on your list. Kim says it's a favorite year-round.
2. Park City, Utah
If convenience is high on your list, Park City is hard to beat.
It's easy to get to from Salt Lake City, making it a great option for a quick ski weekend. You can spend less time traveling and more time enjoying the slopes, restaurants, shops, and mountain town atmosphere.
Kim says Park City is one of Key.co's most popular destinations, and they have a wide variety of accommodations there.
You can choose from:
Large luxury mountain homes
High-end condos
Homes with unique architecture and design
Different ski areas, including Deer Valley
Properties that work well for both smaller groups and larger families
Park City is especially appealing if you want the feel of a mountain getaway but don't necessarily want to stay in a massive vacation home.
And compared with Telluride, it's a much easier choice for a three-day weekend.
3. Big Sky, Montana
If your priority is skiing, Big Sky should definitely be on your radar.
Kim describes the mountain as massive, with tons of terrain and lifts that connect throughout the resort. It's also a great destination for ski-in, ski-out accommodations.
One of Kim's favorite experiences was staying in a home where she could literally ski down the trail and arrive right back at the house. Talk about convenience!!!
Big Sky also has a slightly more remote feel compared with destinations like Park City or Telluride. The town has been growing quickly, but it still feels more like a cozy ski village than a bustling mountain town.
Why Choose Big Sky?
Massive ski area
Lots of terrain
Great ski-in, ski-out options
Beautiful mountain views
More remote and peaceful atmosphere
Homes often include dedicated ski or snow rooms
Great option for spending more time at your vacation rental
Big Sky may not be the destination to choose if you're looking for tons of shopping and high-end restaurants. But if you're happy to spend your evenings cozied up in a beautiful mountain home, it's a fantastic choice.
And with grocery delivery and private chefs available, you don't necessarily need to leave the house much at all.
4. Breckenridge, Colorado
Breckenridge is one of Key.co's most popular destinations and was actually their top-searched destination when this episode was recorded.
Compared with Telluride and Big Sky, Breckenridge has a larger-scale feel. There are more hotels, restaurants, and visitors, so it feels more like a traditional, bustling ski town.
That popularity is also something to keep in mind when booking.
Kim says homes in Breckenridge tend to book quickly, especially around holiday weekends.
If Breckenridge is calling your name, it's worth starting your search early so you have more options.
What Makes Breckenridge a Great Choice?
Easy to get to
Large variety of vacation rentals
Plenty of restaurants and amenities
Bigger ski-town atmosphere
Popular with families and groups
Lots of options for larger homes
Kim recommends booking as early as August or September if you have your heart set on a particular property or holiday weekend.
5. North Lake Tahoe, California
Last on the list is North Lake Tahoe, which offers something the other destinations can't quite compete with: the lake.
While Kim hasn't personally skied North Lake Tahoe, she says it's one of Key.co's most popular destinations and that the homes there are beautiful.
And of course, there's Lake Tahoe itself.
The combination of snow-covered mountains and the lake creates a completely different setting from the other destinations on this list.
Why North Lake Tahoe?
Gorgeous lake views
Beautiful vacation homes
Great skiing
Unique mountain-and-lake setting
Beautiful year-round destination
If you've visited Lake Tahoe in the summer but haven't experienced it in the winter, this could be a fun way to see a completely different side of the destination.
Book the House First
One of Kim's biggest pieces of advice for planning a ski vacation is to book the vacation rental first.
Restaurant reservations, activities, and other services can often be figured out closer to the trip. But if you're looking for a very specific home with the perfect number of bedrooms, a hot tub, a fireplace, and ski-in, ski-out access, your options will become more limited as the season gets closer.
Kim says August and September are when many travelers are already booking their ski trips, especially for popular destinations and holiday weekends.
So if you're thinking about a winter getaway, now is the time to start looking.
Let Someone Else Do the Planning
One of the things that stood out to me most about Kim's approach to vacation rentals is that Key.co isn't just about finding a beautiful house.
Their team can help travelers find the right property based on what they're looking for, and the trip can include additional services like:
Grocery delivery
Private chefs
Massage therapists
Babysitters
Drivers
Ski valet
Other personalized services
Key.co also has a reservations team that can help travelers find a home without spending hours searching through listings themselves.
You can tell them where you want to go, what you're looking for, or even let them help you decide on the destination.
And according to Kim, there is no additional fee for this planning assistance.
Their philosophy is essentially to make memories, not plans, which feels especially appealing when you're the person in your family or friend group who always ends up organizing everything.
Start Planning Your Winter Getaway
Whether you're looking for a quick ski weekend in Park City, a cozy mountain escape in Big Sky, a classic ski town like Breckenridge, the lake views of Tahoe, or the charm of Telluride, there's no shortage of incredible winter destinations to choose from.
And if there's one takeaway from Kim, it's this:
Start looking early.
The perfect vacation rental can make the entire trip, especially when you're traveling with a big group or multiple generations. Find the house that gives everyone their own space, has plenty of room to gather, and makes it easy to enjoy the mountains together.
Now we just need to make it through the rest of summer first. And hopefully, we're in for a very snowy winter!