A Winter Escape to Jackson Hole: Skiing, Western Charm & the Four Seasons

Getting there

Jackson Hole is easier to reach than many travelers expect. From the New York area, United Airlines flies direct from Newark, while Delta Air Lines typically connects through Salt Lake City or Atlanta. American Airlines offers service through Dallas. From the West Coast, all three airlines—Delta, United, and American—operate routes from Los Angeles, while both United and American also fly from Chicago.

One essential stop after an early morning flight: Cowboy Coffee Co. A strong coffee here is practically a Jackson Hole rite of passage.

Jackson vs. Teton Village: Where to stay

Visitors typically choose between staying in Jackson or Teton Village, and each offers a very different experience.

Jackson puts you right in the heart of town, with easy access to restaurants, art galleries, boutiques, and nightlife. It’s ideal if you want a lively Western atmosphere and the ability to wander through town after a day outdoors.

Teton Village, on the other hand, sits directly at the base of Jackson Hole Mountain Resort. Staying here means true ski-in/ski-out access, immediate proximity to après-ski spots, and dramatic views of the Tetons. It’s the easiest and most seamless experience for serious skiers.

For our trip, that convenience made the choice easy.

Staying at the Four Seasons Jackson Hole

Four Seasons Resort Jackson Hole is the only true ski-in/ski-out resort in Teton Village, making it one of the most coveted places to stay in the destination.

The resort has about 150 rooms, suites, and residences, all notably spacious. Suites begin at one bedroom, and the residences extend up to five bedrooms, making the property well suited for couples, families, and larger ski groups.

We stayed in a Valley View Room, the second room category up, and it beautifully reflected the design spirit of Wyoming. From the tree-like carpet to the mix of stone and wood throughout the room, every detail felt intentional. Brown, tan, and emerald accents combined with a backlit headboard and fireplace created a warm alpine feel.

At 550 square feet, the room offers generous space with either a king bed or two double beds, a fireplace, a seating area with a table and chairs, benches, and a patio with a chair to take in the views. There’s also ample storage—including a walk-in closet to hold bulky winter gear—and a bathroom with double vanity sinks, a soaking tub, and a separate shower.

Skiing made seamless

One of the biggest perks of staying at the Four Seasons is the ski concierge. After getting fitted for your skis or snowboard, the team stores your gear at the base of the mountain. Each morning it’s waiting outside on a rack—no carrying equipment or navigating crowds required.

After a full day on Jackson Hole’s famously challenging terrain, the resort’s heated outdoor pool and hot tubs are essential. There’s also a full spa and large fitness center, perfect for unwinding after long ski days.

Après-ski: Where the fun begins

Après-ski is a major part of the Jackson Hole culture. Inside the Four Seasons, The Handle Bar is one of the village’s most iconic après spots. Located right at the base of the mountain, it’s a lively scene with DJs, cocktails, and front-row views of skiers coming down the slopes. As hotel guests, we were able to snag an incredible table by the fire.

Just steps away is the legendary Mangy Moose, known for live music, quirky decor, and a high-energy après crowd. It’s been a Jackson Hole institution for decades and is well worth experiencing.

Dining highlights

The Four Seasons offers several dining options including Steadfire Chophouse, where breakfast is served daily, as well as Ascent Lounge and a convenient grab-and-go outlet.

One hidden gem is 80 Proof, a speakeasy exclusively for hotel guests. The cocktail menu is presented in a book, and each drink is incredibly thoughtful and creative. It turned pre-dinner drinks into an experience of its own.

Breakfast is another standout perk. As a Four Seasons Preferred Partner, my clients receive daily breakfast for two, which is an exceptional value.

Exploring the town of Jackson

Even if you’re staying in Teton Village, spending time in the town of Jackson is essential. The streets are lined with independent boutiques and galleries, making it a fun place to wander. Shops like Made highlight locally made goods and unique Western finds. For a true Jackson Hole souvenir, visit Kemo Sabe, where custom cowboy hats are crafted in store. They’re definitely an investment—but absolutely worth it.

For breakfast or a mid-day stop, Persephone Bakery is a favorite. The bakery serves excellent pastries, coffee, and light fare in a cozy setting.

Honorable mentions: Where to eat

While the Four Seasons dining is excellent, a few other restaurants stood out during our stay. Our favorite meal of the trip was at Corsa, located inside Caldera House. The Italian menu is outstanding and the atmosphere feels intimate and elevated. We also loved Teton Thai, a local favorite known for bold flavors, and Snake River Grill, one of Jackson’s most iconic restaurants.

Why Jackson Hole is so special

Jackson Hole combines big-mountain skiing, authentic Western culture, and luxury hospitality in a way that few destinations can replicate. And if ski-in/ski-out convenience is a priority, Four Seasons Resort Jackson Hole delivers one of the most seamless mountain experiences in the country—making it an easy recommendation for travelers looking for an unforgettable winter escape.

Summer in Jackson Hole

Jackson Hole is just as spectacular in the summer, when the mountains shift from a ski destination to an outdoor adventure hub. Long days are perfect for hiking, biking, fly fishing, and scenic drives through Grand Teton National Park and Yellowstone National Park. One of the most memorable experiences is a wildlife safari at sunrise or sunset, where you might spot bison, elk, moose, bears, and bald eagles against the dramatic Teton backdrop. Guided stargazing is another highlight thanks to the region’s minimal light pollution—the night skies here are incredibly clear, making it one of the best places in the U.S. to see the Milky Way.

• Choose your base wisely: Staying in Jackson puts you close to restaurants, galleries, and nightlife, while Teton Village offers true ski-in/ski-out access at Jackson Hole Mountain Resort.

• Arriving is part of the experience: Jackson Hole Airport is the only commercial airport located inside a national park, meaning incredible views as you fly in.

• Ski terrain is serious: Jackson Hole is known for steep runs and advanced terrain, but there are still plenty of options for intermediate skiers as well.

• Don’t skip town time: Spend time wandering the shops in Jackson, grab coffee at Cowboy Coffee Co., and stop by Persephone Bakery for pastries before heading back to the slopes.

For more inspiration and insider recommendations, visit our Jackson Hole page.