Outpost Jackson Hole

Vacation Rentals in Jackson Hole

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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. 

Fill Labor Day Weekend with the Best of Jackson Hole Summer

We can emphatically say that summer should last an extra month. With a plethora of activities to take advantage of, the long days spent outside soaking up the rays are some of the best in Jackson Hole. But time has that funny way of staying consistent, and our days of summertime are limited. That’s why we always like to fill our Labor Day Weekend with the best of Jackson Hole summer. We’ve compiled a full weekend of activities for you to enjoy every second you have in our special neck of the woods. We hope you’ll join us in celebrating the close of summer in Jackson Hole! 

Friday
Kick off your Labor Day Weekend in Jackson Hole with a trip to the backside of the Tetons. A little known secret: the Idaho side of the Teton range offers stunning views of the mountains. Home to many of those who keep the wheels spinning here in Jackson Hole, we encourage you to take a peek into our community that you simply won’t get without a visit to Idaho. 

Start your day with breakfast at Butter Cafe. The sister restaurant to ever popular Streetfood in Wilson, this charming breakfast joint is the perfect spot to fuel up for your day of adventure. If you’re feeling up for a big hike, Table Mountain is a 12 mile round-trip hike. Landing you right next to the Grand Teton, you’ll have incredible views of our favorite mountain range. If you’d like something less strenuous, the Darby Canyon Wind Cave hike is a beautiful 6 miles out-and-back. After your day in the Tetons, grab an early dinner at Teton Thai in Driggs (we recommend the Pineapple Fried Rice with Crispy Duck, or Bison Pho), and end your day perusing the many beautiful Arts and Crafts during September’s First Friday Art Walk in Driggs. Bonus: take in the stunning sunset over Jackson Hole as you drive back over Teton pass.  

Saturday
After your big day of hiking, enjoy a lazy morning breakfast at Snake River Roasting Co.’s beautiful cafe just off Town Square. We recommend the Bison Benedict and getting a Cinnamon Roll to share. Who doesn’t love a good breakfast appetizer? And don’t forget to grab a bag of their hand-roasted coffee to bring home with you! 

Next head over to the Saturday Farmers Market. Open from 8 a.m. – 12 p.m., there’s no rush to get there super early! Be sure to grab some locally grown produce and steaks for a grill-out at your rental later today. Once you’re all stocked up, mosey down to Snow King Mountain Resort and spend a day frolicking (yes truly) with a Big King Pass. From ziplines, to ropes courses, an alpine slide, miniature golf, and so much more, your day will be filled with shrieks of laughter and maybe just a little adrenaline. Head back to your rental and fire up the grill for a quintessential Labor Day Weekend BBQ. 

Sunday
After two days packed with activities, treat yourself (and your body) to a stretch with yoga on the rooftop of the Cloudveil, followed by brunch downstairs at the Bistro. Be sure to make a reservation. When you’re ready to kick it back into gear, head out to Teton Village for Sunday Funday. Enjoy $20 lift tickets and 20 percent off bike rentals, and spend your afternoon exploring their epic downhill mountain bike terrain. Once you’re ready for a beer (or three) and some delicious food (we recommend the lamb burger, tacos, or bibimbap), head over to Streetfood at the Stagecoach. Pro tip: stick around for line dancing at “Church.” Bill Briggs (the first person to ski the Grand!) and his band has played there every Sunday for the past 40 years.  

Monday
We know, you’re tired. It’s been a long weekend FULL of activities. Grab some sandwiches from Creekside and head up to String Lake in Grand Teton National Park for a lazy lake day with incredible Teton views. Be sure to bring your bathing suit as this is the perfect swimming hole. We recommend finishing your trip with a delicious dinner at Trio before heading home. Be sure to make a reservation, and definitely order the Blue Cheese Waffle Fries. You won’t regret it. 

We hope you’re able to pack in as much of our favorite summertime activities during your Labor Day Weekend in Jackson Hole. Maybe we’ll see you out there as we do the same! 

BROWSE LABOR DAY WEEKEND AVAILABILITY

End Your Summer on a High Note in the Mountains

One of our favorite things about summer vacation is the utter abandonment of your calendar. Forgetting the date and letting time float by makes us nostalgic for the ice cream filled summer days of our childhood. But just like it did when we were kids, Labor Day Weekend is signaling the final hoorah of the summer. End your summer on a high note by spending August in the mountains before autumn blows in the shorter, cooler days. Lucky for us, the blurry, golden haze of late August in Jackson Hole offers some of the best days we get. Make sure to book an Outpost vacation rental today, and get excited for your late summer getaway!

Fishermen enjoy a beautiful late summer day on the water.

For the BBQ Enthusiast 
Take advantage of your back deck, and enjoy the smokey, grilled flavors of summer from your BBQ. Our local farms are at the height of their production, so make sure to pop through the Farmer’s Market over Labor Day Weekend, or hit up the Wednesday People’s Market through the rest of August and September. Don’t forget to swing by Sweet Cheeks Meats for cuts of the best locally sourced meat around. Insider tip: go for the ribeyes, they’re worth every penny!

For the Avid Flyfisherperson
This is the best time of year to cast your line. The river is at its lowest point, the hatches are buzzing, and the cooler nights and mornings bring more active, biting fish. As the golden hues of August spread into the aspen trees, the views from the river get even better. Book your guided fishing trip today. 

For the Animal Enthusiast 
Though the elk aren’t bugling quite yet, the turn of the season is a great time to view wildlife. Book a wildlife safari and experience the exquisite animals who call this place home. (Staying at an Outpost property? Please contact our guest relations team for a discount code. 307-690-4790 / salescrew@outpostjh.com.)

Looking to get up close and personal? Book a horseback ride through the foothills of the Teton Mountain range. With no sound but the gentle clip of hooves on dirt, you’ll feel transported to a time long past in our beautiful valley.

For the Artist
From August 5-7, come enjoy the 57 Annual Art Fair in Jackson Hole! Beckoning work from local artists, and artists from around the region, this much anticipated event showcases a wide array of pieces. Otherwise, spend a morning immersed in some of America’s most celebrated painters and photographers at the National Museum of Wildlife Art. Finish your tour with views of the Elk Refuge with lunch at Palate. After being inspired by the museum’s incredible collection, take a walk through the many galleries downtown. Who knows, you might find something you just can’t go home without! 

While we’re sad to see the final days of summer approaching, August ushers in a beautifully slow, even romantic transition to fall. Book your end of summer getaway to join us in celebrating the last of this incredible season, and welcome in the early splashes of autumn in Jackson. 

Summer is in Full Swing in Jackson Hole

Adrenaline-fueled shrieks of laughter reverberate through the Hoback canyon as fleets of rafts splash through the whitewater. At each of the four corners of Town Square, friends, lovers, and families cling to each other as they pose under the iconic antler arches. Throughout the evenings, joyful sounds of live music spill onto the streets. Summer is in full swing in Jackson Hole. 

Summer revelers white water raft down the Snake River.

We’re all holding on to that insatiable summer energy and appetite. Bouncing from one activity to the next, there’s a gentle reminder of cooler days to come hanging in the air. It’s time to recharge before the school year and take advantage of every day you have left. With an abundance of summer activities, concerts, and events to enjoy, there’s no better way to fill your last days of summer than in the mountains of Jackson Hole. 

Traveling with a group? Choose an Outpost vacation rental in Teton Village as the home base for your vacation. From mountain biking to rope courses, hikes, spas, and so much more, there are a plethora of activities just footsteps from your door when staying in our luxurious Granite Ridge Chateau, Shooting Star Lodge 1, or Timber Ridge 9 homes. Located at the base of Jackson Hole Mountain Resort, these homes are ideal for large group getaways. In the evenings, take advantage of the exceptional lineup of musicians playing through the end of August at the Grand Teton Music Festival, as well as the many wonderful dining options in Teton Village. 

If you want your August getaway closer to downtown Jackson, we recommend booking your stay at one of our One Town Hill condominiums, East Gill 4, or Grand View 5140. Each home features a unique style and offers that home-away-from-home experience for all visitors. Stay within walking distance of the rodeo, live music and line dancing at the famous Cowboy Bar, a large array of fabulous restaurants, and everything else that August in Jackson Hole has to offer. 

If you’re looking for a more secluded experience of the Tetons, the Teton Retreat, Golf Creek 35, or Teton Shadows Owen E Outpost vacation rentals are perfect for you. While each boasts unique and stunning Teton views, these homes will also give you the space you desire, with the convenience of an easy drive to downtown, Teton Village, and Grand Teton National Park. Bonus: one perk of being more secluded is the increased likelihood of wildlife sightings!

While we wish there was a way to slow down the clock, our sun-filled days of summer in the mountains are beginning to feel numbered. The best way to stretch out the time is to use every last day of summer that you can. We can’t imagine a better way to do so than a summer getaway right here in beautiful Jackson Hole.