Outpost Jackson Hole

Vacation Rentals in Jackson Hole

Skiing/Snowboarding

Ski Season is Just Around the Corner

As the hottest season begins to wind down and we all scramble to squeeze in every last moment with our summer sport, there’s an unavoidable hum beginning to reverberate through the valley: ski season is just around the corner. And while the whole winter is reason enough to celebrate, filled with festive concerts, fairy lights, and fireworks, the holidays are always a busy time of reverie here in Jackson Hole. Be it Thanksgiving, Christmas, New Years, or President’s Day Weekend, we don’t want you to miss your chance at joining in on the most festive times in the Hole! With lift tickets on sale and properties beginning to fill up, now is the perfect time to book your trip. Bonus: streamline your vacation plans by reserving lift tickets through us when you book your vacation rental for this winter. 

The birthplace of freeskiing, Jackson Hole is truly a skier’s mecca. We don’t need that first snowflake to make its appearance in early October (yes, October) to start pulling out our gear and assessing whether or not it’s time to invest in updates. At this point in time, most of us have already bought our season pass to Jackson Hole Mountain Resort and are waiting with bated breath for a long winter filled with ski laps, snuggling up for hot chocolate and waffles in Corbet’s Cabin, and apres nachos at the Spur. 

If you’re lucky enough to be here when the lifts start to spin over Thanksgiving weekend, you’ll be swept up in the action as the palpating anticipation is unleashed on Teton Village signaling the start to another joy-filled winter season in Jackson Hole. For the next 5 months, prayers and whispers for “Cowboy Powder” will hang in the air. And when that Christmas snowfall arrives, you’ll be grateful to have planned ahead. 

Whether you’re coming with your partner, family, or a group of friends, each Outpost vacation rental features fully functioning kitchens to host your holiday celebrations. That being said, we know that cooking through the holidays isn’t for everyone. After all, we know what it’s like to wish we were out on the slopes and not basting that turkey or chilling the pie dough! Be sure to reach out to Provisions for exceptional catered meals, either prepared in-house for an elevated at home dining experience, or delivered straight to your door for your convenience. 

Regardless of when you’re hoping to get out for a ski holiday, we’re here to provide you with the best home base for your vacation. With options at the foot of the mountain resort, a short drive away on the West Bank, or close to the nightlife in downtown Jackson Hole, we’ve got vacation rentals for whatever you might need. Book today to lock in your Jackson Hole ski holiday. 

Romantic Getaway Guide to Jackson Hole

No matter how you feel about Valentine’s Day, we can all agree that Jackson Hole has been well below freezing lately, and it’s the perfect time to cozy up to your favorite companion —human, dog, or otherwise. Here’s your guide to finding romance in the chills of winter. 

Our team at Outpost has created a romantic getaway guide to Jackson Hole. No matter if you’re looking for a delightful staycation or visiting us from afar, we all deserve a little more love in our lives. After a rather interesting few years, Valentine’s Day 2022 couldn’t come any sooner. And hey, we get it… planning worthwhile couple activities can be challenging—we’ve got you covered. 

A couple ride the ski lift together during their romantic getaway to Jackson Hole, WY.

Plan a Romantic Getaway to Jackson Hole

No Valentine’s Day is alike, but there are certainly a few key places we like to enjoy with our sweethearts. You can pick and choose from the recommendations below, creating your personalized romantic getaway in Jackson Hole! 

For the Foodie

Start your mornings off right with an Indulgent breakfast (or coffee) date at Persephone. The cinnamon brioche and egg sandwich are our favorites! You can pick up a “Bake-At-Home” batch and share it with your loved ones (or not). 

We all can’t be early risers. It’s alright though; our favorite date night spots are perfect for you! Sit side-by-side at Sudachi’s sushi bar, located on Wilson Westbank, and indulge in a nightly chef’s tasting menu (omakase). Venture to the Town of Jackson and share some delicious hand-made pasta at Glorietta. Staying near Teton Village? Throw on your favorite ski sweater and go straight from the après at the Spur to elevated wood-fired pizza at Osteria. 


For the Adventurers

In addition to our appetite for good food, we love spending intimate time with our partners in the great Jackson Hole outdoors. Drive out to watch the sunset/sunrise in Grand Teton National Park – you can’t go wrong with the views from any of the main pullouts. Plan a fun ski day together at Jackson Hole Mountain Resort (JHMR) and create thrilling memories— be sure to ride on the cozy two-seater Marmot chair! 

Stay with Outpost

Your love deserves the world, and that’s exactly what a romantic Jackson Hole getaway provides! Gain a refreshing perspective and appreciation of one another when you stay in Outpost’s one and two-bedroom vacation rentals. These private retreats will only bring you and yours closer this winter.

Enjoy a Unique Spring Break in Jackson Hole

Jackson Hole is a breathtakingly unique year-round destination for vacations, and spring break is no exception. Travelers come from far and wide each spring to enjoy our world-famous Wyoming powder skiing. If skiing isn’t your thing, our valley has a variety of other adventures and activities as well. The last of the Old West, Jackson Hole boasts iconic landscapes, captivating local history, and much more. Your spring break this year in Jackson Hole will be one to remember.

 Outpost is here to help elevate your Jackson Hole spring break. With homes throughout the valley, our vast vacation rental portfolio will place you right in the midst of all the spring break action—or not if you are looking for a more laidback getaway. Whatever you desire, Outpost has something perfect for you! Additionally, our company works with you in mind, which is why we offer fantastic amenities and guest services. You’ll be right at home when you stay with Outpost this spring break—keep reading to learn more!

Spring Break in Jackson Hole

As mentioned, Jackson Hole is filled with many spring break activities that are perfect for you. No matter what your ideal Jackson spring break looks like, Outpost has you covered! We have compiled a few quintessential activities and amenities below. 

For the ski-centric visitor:

Jackson is one of the top ski destinations in the world. Folks come from all over just to rise early and ski all day! If skiing is your main reason for visiting, we recommend staying right in the heart of the mountains at one of our many vacation rental options in Teton Village. Now that your lodging is sorted out, let’s take care of your skiing needs. Outpost has partnered with top ski resort Jackson Hole Mountain Resort (JHMR) to offer money-saving Lift Ticket & Lodging packages. You save money and time when you bundle your lodging with JHMR lift tickets through our online booking engine. Your lift tickets will be in your rental upon arrival so you can start your adventure the next morning! For more up-to-date information, call us at (307) 690-4790.

For those who don’t ski:

While Jackson is a famed ski destination, those who don’t ski can still experience a worthwhile spring break. Your little ones will be awe-struck during a horse-drawn sleigh ride through the National Elk Refuge, where you’ll get up close and personal with these extraordinary animals. Grab a sweet treat from our friends at Persephone Bakery before wandering around the local businesses in historic Town Square. Your trip is not complete without a photo at Jackson’s Elk Antler Arches in Town Square. These iconic landmarks were first built between 1966 and 1969. And finally, get away from it all with a day trip to our treasured Grand Teton National Park and Yellowstone National Park. 

We’re Here to Help

Outpost is here to help with all your Jackson Hole spring break needs. We exclusively rent out baby gear, outdoor gear, and also offer grocery delivery to our homeowners and guests. From boot heaters to portable baby chairs, you’ll be prepared! Your rental items will be delivered prior to check-in and removed when you check out. Visit our Outfitted website for more details. 

Find Your Home Away from Home with Outpost Vacation Rentals

Spring break in Jackson Hole will undoubtedly be one to remember! After a long day of skiing or exploring Jackson, relax in a stunning Outpost vacation rental filled with all the furnishings of home. From cozy townhomes to spacious family homes, we have a little bit of something for everyone. Book your spring break stay with us online today!

Skinning the King

It’s 6pm and the sun is setting as I click into my skis, my breath sharp in the February cold snap. The summit of Snow King glistens almost 2,000 vertical feet above me, and I turn to my friend just to make sure we really don’t want to bail.

“Oh, come on,” he says knowingly, and he starts to make his way up the steep incline, the skins on his skis setting our rhythm. I sigh and gear up for a good sweat. Before we reach the first switchback, the stress of the work day dissolves, and we’re chattering on about last week’s storm and the spots we want to ski over the weekend. Other headlights dot the skinning trail above and below us, a small community created each morning (for the truly brave) before work and each evening after work.

It’s quite possible we’re taking part in one of the oldest traditions in Jackson Hole. All year long, the steep hills stretching to the summit of Snow King linger over its residents, calling us to the outdoors, a centerpiece of the town that doesn’t give us the excuse of a long drive or any other reason to blow off a work out. In the summertime, we scatter the hills walking, running, biking — in the winter, it’s skinning time.

About the time we reach the midway station, the view really starts to glamour up. The lights of our small town glow, cozy cabins dotted below lazy smoke streams from wood stoves. A group passes us on their way down, hollering out hellos and biding good wishes for the summit. The mountain is open for night skiing, and kids are still hopping off the chairlifts and gliding out under the night skiing lights. There’s a reason they say there’s no place like home….

The second half of the switchbacks is where it gets good; the lights end at the midway station, leaving room for the western sky to open, stars laid out horizon to horizon, the milky way bold and outspoken without any cloud cover.

About an hour after we start, we’re at the summit. It’s a night with no wind, so we take our time putting our layers back on and pulling off our skins. Our gift is standing between two views that never grow old — the entire town of Jackson and the entire open sky (filled with shooting stars on the clear nights….no, seriously) — both indescribably beautiful until you see them for yourself.

Then we’re off, a single, perfect ski run waiting for us. With new powder at the top, we grab fresh tracks and giggle our way through pillows of snow. My stomach bubbles with utter joy when I see the grooming machine has already been out: that means the second half of our run is warm, buttery, delightful corduroy. There’s really nothing better — except knowing now we can go out to eat anything we want without feeling guilty.