The 4 Best Winter Getaways to Embrace the Cold

When winter strikes, you can either hide indoors or lean into the season. I’ll always choose the latter. I suspect you would, too, since you’re reading this. I’ve visited every getaway on this list, and I can tell you firsthand that any of them will satisfy your winter-sports itch. Whether you’re a skier, a snowboarder or just looking for a fun winter getaway, these are my picks. And if you book with Rakuten or shop with Rakuten to pick up some gear, you’ll earn Cash Back on your purchases.

Most people think great skiing and snowboarding can be found only in the West, but Killington proves otherwise. This East Coast resort offers world-class skiing, snowboarding, tubing, dining and entertainment. It’s also more affordable than its West Coast counterparts, and it makes for an excellent last-minute vacation spot.

What to Pack: Killington can get frigid at times because it’s the tallest object in the area and the wind can pick up around the peak. Pack a warm jacket, such as the Burton Covert, to keep yourself toasty while on the slopes. It has thin but powerful insulation for even the coldest days on the mountain.

Where to Stay: Check out the Chalet Killington, which is a few minutes from the slopes. The hotel offers free breakfast and a ski shuttle to Killington to save you some cash during your stay.

Whistler Blackcomb

If you’re searching for the ultimate winter getaway, look no further than Whistler Blackcomb in Whistler, British Columbia. This massive ski resort has long been one of the best places to travel in winter because of its impressive ski conditions and near endless trails to explore. With two mountains to cover, you’ll never run out of things to do.

What to Pack: The conditions change at Whistler quite often, so you need to be prepared. At the top of the mountain, you’ll find yourself above the clouds and in need of a good set of goggles to protect your eyes from the harsh sun. My pick? The Tsar goggles from Bolle. The dark lens is a perfect match for sunny days on the slopes.

Where to Stay: The Listel Hotel is a highly rated pick, and it’s within walking distance of the gondolas for both mountains. I stayed there years ago and had a great experience. There’s even a free ski check when you finish your day, so you don’t have to lug your equipment to and from the hotel.


Jackson Hole Mountain Resort is one of the best resorts I’ve ever visited. The skiing and snowboarding is top-notch, and there’s plenty to do in town after a long day on the mountain. It’s widely regarded as one of the best places to travel in January because of the snowfall.

What to Pack: With all the fresh powder you’re bound to experience in Jackson Hole, you’re going to need a good pair of waterproof ski pants. Marmot’s Durand pants fit the bill. They’re completely waterproof and breathable to keep you dry all day and night.

Where to Stay: There are plenty of pricey hotels to stay at in the Jackson Hole area, but if you’re looking for a cheaper hotel with all the bells and whistles, the Snake River Lodge & Spa is an excellent choice. It’s central to all the action and offers all the amenities you can ask for.


When you think of Colorado ski resorts, Aspen and Vail come to mind — but Breckenridge should be at the top of your list. This mountain is situated about an hour and a half from Denver, and several other resorts are close by. Aside from the skiing and snowboarding, you can enjoy snowcat tours, tubing and even a roller coaster.

What to Pack: With all the activities available at Breckenridge, you’re going to want to spend a lot of time outdoors. That means you’ll need a warm pair of gloves, like the Propulsion GTX gloves from Spyder. They’re waterproof and warm, but still allow for proper finger movement. Plus, Spyder is one of the leading suppliers of ski gear.

Where to Stay: The Lodge at Breckenridge is a fantastic and affordable choice. It’s situated just outside of town, but the free shuttle to and from mountain will take care of your transportation needs. There’s also an on-site restaurant and bar if you want to relax a little closer to where you’re staying.

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