A One Week Winter Retreat in Jackson Hole: Where to Stay, What to Do, and Places to Eat

They say Jackson Hole is for people who find Aspen a bit too “loud.” But don’t be deceived: Jackson Hole makes an impression before you even touch the ground. Your arrival is via the only commercial airport in the United States located entirely within a National Park, which makes for a dramatic descent amongst the peaks of Grand Teton. It is perhaps no coincidence that private planes outnumber commercial flights here by 2:1 each year.

For nearly a century, the town has become a premier winter retreat of the American West, a place where rough-hewn log cabins hide five-star spas and world-class dining. It’s a place that invites you to have it both ways: witness the brutal, unvarnished beauty of Wyoming but from a vantage point of absolute refinement.

At its heart, this is a skier’s town. Yet, the valley has evolved into a "choose your own adventure" destination. For every expert dropping into a vertical chute, there is someone else embarking on a winter safari through the National Elk Refuge to witness moose and bighorn sheep against the white expanse.

Each winter, my family picks a different ski town to spend the holidays. We’re an even split between skiers and non-skiers, so we need a place that works just as well for someone on the slopes as it does for someone exploring town. In other words, we put as much effort into finding the best mountain runs as we do seeking out the best coffee and pastries. After an entire week in Jackson Hole, here’s everything that I’d tell my friends if they were considering a trip to one of the most breathtaking and beloved towns in the country. 

Where to Stay

Deciding where to drop your bags is the most critical logistical choice you’ll make in the valley. The geographic divide is simple: you either stay in Teton Village (slopeside, resort-heavy, and quiet after dark) or the Town of Jackson (twelve miles away, walkable to bars/shops, and humming with a year-round pulse). Both have their merits, but it’ll depend on what you and/or your group are looking for.

Hotels

If you are coming to Jackson to be pampered, the competition is fierce. The Four Seasons Resort in Teton Village remains the undisputed heavyweight. It is the only true five-star, ski-in/ski-out experience, and while the price tag is eye-watering, the "Ski Concierge" alone (who warms your boots and carries your skis to the snow) might make you forget the bill. 

If you want luxury but prefer the energy of the town, there’s The Cloudveil. As part of the Autograph Collection, it’s remarkably polished, featuring a rooftop terrace that overlooks the iconic antler arches and a guest pantry on every floor stocked with high-end local snacks. It’s the kind of place where you’re steps away from the best cocktails in Wyoming, yet still have access to a private shuttle that whisks you to the mountain in twenty minutes.

It’s also worth noting that Aman's legendary cliffside property, Amangani, is currently closed for an extensive refurbishment and is slated to re-open in summer 2026.

For a more affordable stay, the Anvil is the town’s standout. A reimagined 1950s motor lodge, it pays homage to the site’s original owner, a local blacksmith, with a "frontier-chic" aesthetic. Credit goes to Brooklyn-based Studio Tack, who spent a year in the valley to ensure the details, from iron bed frames to Woolrich blankets, rang true. Its lobby serves as a cozy community hub with a wood-burning stove and a serious coffee program, though the real draw is the onsite restaurant, Glorietta Trattoria (more on that below).

The Airbnb Play

If you’re traveling with a group, getting a house in Jackson Hole is probably your best move. It’s also what my family decided to do, and we couldn’t have been happier.

After researching countless Airbnbs, VRBOs, and other condo rentals in the area, we stumbled upon Amásé Stays, a boutique collection of luxury rentals that feel less like a generic vacation house and more like a curated private home. What set them apart from the sea of standard mountain condos was the impeccable attention to detail: the cookware was premium All-Clad, the furniture was from Audo Copenhagen, and the aesthetic felt like a spread from Architectural Digest. 

Most of their Jackson Hole properties are located in the center of the Arts District in downtown, which made it the perfect home for us since it was steps away from great restaurants and shops and a quick car ride to Mountain Resort. Staying with Amásé also gave us the ability to cook meals at home, decompress in private, enjoy a private hot tub on our outside deck, and, of course, put up a Christmas tree in the living room!

What to Do

While the iconic "Big Red" aerial tram is the valley’s spiritual center, Jackson Hole is far more than just a skier’s pilgrimage. The true allure of a winter holiday here is the "choose your own adventure" aspect: you can spend your morning skiing at Mountain Resort and your afternoon in a steam-filled spa or a horse-drawn sleigh. The challenge lies in finding ways to fit everything you want to do into your schedule.  

The Mountain

Jackson Hole Mountain Resort is world-renowned for its difficult terrain, and while I wouldn’t recommend complete beginners learn to ski here, the "expert-only" reputation is a bit of a myth. The resort has invested heavily in easy-to-intermediate terrain, making it plenty accessible for folks who aren’t black diamond level. 

If you want to tackle the mountain like an insider, consider hiring an ace guide. While the price is steep (nearly $900 for the day), it allows you to cut the lift lines and find "secret" powder stashes that remain untouched days after a storm.

The Winter Safari

If you aren't on the slopes, the valley floor offers a “winter safari” that is wholly unique to the area. The National Elk Refuge sleigh ride is a classic Jackson move, where you can observe thousands of elk and other wildlife in one of the largest wintering grounds in the country. If you’ve rented a car, you can also be your own guide. There are plenty of open roads, like the Kelly Loop or Antelope Flats, where you can frequently spot moose and bighorn sheep just by driving slowly and keeping your eyes peeled.

Backcountry Adventures

Perhaps the best full-day activity we did was snowshoeing with Eco Tours in Grand Teton National Park. My family loves to hike in the summer, and snowshoeing provided the perfect winter equivalent. It’s peaceful, accommodating to all skill levels and ages, and provides great aerobic exercise. Guided by a naturalist, we were able to traverse deep, untracked powder to reach Taggart and Bradley Lakes – breathtaking, natural gems that are surely stunning in July, but take on a different level of beauty and stillness in January. 

For a more high-octane adventure, snowmobile tours offer access to the vast backcountry regions that remain otherwise unreachable during the winter months. While a trip into Yellowstone to see a frost-covered Old Faithful is the most famous route, it is far from the only option. Thousands of miles of groomed and off-trail terrain exist just outside the park boundaries. Togwotee Pass is a legendary destination for those looking to experience deep powder and wide-open meadows, while the Gros Ventre Range provides a more rugged, scenic escape with frequent wildlife sightings.

Lastly, if you prefer animal over machine, there are expert dog sledding tours that allow you to experience the silent grandeur of the Bridger-Teton National Forest. Led by a team of passionate Alaskan Huskies, you can sit back in the sled or even try your hand at mushing under the guidance of a professional. Many of these teams are led by Iditarod veterans who treat their dogs as true partners. Plus, you get to meet and play with the pack at the end of the trail (which was the real reason our group sought out dogsledding). 

Shopping

Coming from NYC, our group arrived in Jackson with some skepticism regarding mountain town shopping. We expected a surplus of kitschy souvenir shops and predictable outdoor gear outlets…which there certainly were. But we were also surprised to find pockets of the retail scene that were genuinely well-curated. 

One of our first stops was Mountain Dandy, the perfect Western shop to hunt for heavy wool blankets, cozy throws, and unique home goods that feel both high-end and lived-in. Just a few blocks away, Inspiratum Colligere offers a more minimalist approach, focusing on small designer goods and objects that are beautiful, whimsical, and often handmade. Of course, there’s also the quaint town bookstore, Valley Bookstore, that has a great roster of new releases and plenty of local stories to learn about the region’s history. 

For fashion, Habits was the standout. They carry an impressive roster of labels like Guest In Residence, A Kind of Guise, and Knickerbocker. I wouldn’t have been surprised if they told me they had a location in NYC as well. For something with a bit more history, Womenfolk is a must-visit. As a local consignment shop, it is stocked with "gently loved" vintage wares that reflect the valley's unique style, offering a sustainable way to find high-quality pieces at a better price point. If you are willing to drive just outside of town, the Lela Rose boutique is another great stop, offering a robust assortment of western-inspired designs alongside rare vintage items hand-sourced by Lela Rose herself. 

Jackson Hole is also home to some spectacular art galleries, the most prominent of which is Maya Frodeman Gallery. Rather than the traditional "cowboy art" you might expect, this space focuses on a truly sophisticated curation of contemporary artwork and fine jewelry. When we visited, acclaimed artist Bobbie Burgers (one of my mom’s favorites) happened to be running a solo exhibit. 

Where to Eat

The main event of our trip, as is the case every year, is eating. Luckily, there is no shortage of great places to pick from in Jackson Hole, which perhaps should come as no surprise given the type of clientele the town has come to attract. 

The first name you need to know is Persephone. The charming, local bakery and cafe has two locations under the same name, one in downtown and the other just outside of the Mountain Resort. It offers an artisanal selection of baked goods and breads, serves breakfast and lunch daily, and sources much of their produce locally. I’m reluctant to admit our group made a pitstop at Persephone nearly every day of our trip – sometimes just for a coffee, other times for a lunch feast. The Persephone owners Kevin and Ali Cohane also have a second outpost in town under a different name, Picnic, which is slightly slower-paced and larger in size but still serves up their classic pastries and hit lunch menu. 

While our group loves to grocery shop and cook meals at home (thankfully there’s a Whole Foods right outside of town!), we had a number of great dinners out while in Jackson. On our first night, we ate at Kampai, a great contemporary Japanese restaurant with an interior that feels like a slice of Tokyo in the Tetons. The menu focuses on incredibly fresh sushi and innovative small plates. Try to sit downstairs if you can, since upstairs offers a more limited food menu. 

For Italian, there are two names you need to know: Glorietta Trattoria and Corsa. The first is located around the block from the Anvil Hotel, and specializes in wood-fired Italian "soul food" like handmade pastas and charred steaks. Corsa, meanwhile, is located within the famed Caldera House at Teton Village. While it has a more après-ski vibe, it still evokes the rustic charm of an Italian Alpine trattoria. Go here for handmade pastas like spicy vodka rigatoni and lobster linguine, and hearty secondi meant for sharing family-style.

When we were looking for something a bit more casual, Teton Thai was the unanimous favorite. Tucked away near the base of the mountain, we were shocked at just how delicious and authentic the food was. I’ve had plenty of worse Thai food in New York than at Teton Thai. For a different international flair, Figs in the Hotel Jackson offers incredible Lebanese-inspired Mediterranean plates and some of the best hummus and pita in the valley, all centered around a stunning two-story fireplace.

And of course, no trip to the valley is complete without a stop at Million Dollar Cowboy Bar, an iconic landmark right on the Town Square. Cold beer, live music most nights, and a beautiful interior that’s great for group hangs. 

Ultimately, I found Jackson Hole to be a rare destination that actually managed to exceed its lofty reputation, provided you approach it with a bit of a plan. If you are traveling with a group, opting for a private home like an Amásé property is the best way to anchor your trip and enjoy the valley at your own pace. Be sure to rent a car so you can explore the open roads of the park and National Elk Refuge on your own schedule, and remember to book your dinner reservations well in advance to avoid the seasonal rush. 

Most importantly, do not make the mistake of spending your entire week exclusively on the slopes. While the skiing is undoubtedly world-class, much of the magic of Jackson is found in the quiet stillness of a snowshoe trail, the curated racks of a local boutique, and the wood-fired comfort of the town's best restaurants.