Outpost Jackson Hole

Vacation Rentals in Jackson Hole

Jackson Hole Vacation Rentals

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.   

Record-breaking Flooding Temporarily Closes Yellowstone: Updated Information

Mist rises over thermal springs in Yellowstone National Park

Recent record-breaking flood conditions caused a full evacuation of Yellowstone National Park. After temporarily closing the country’s oldest national park, the National Park Service took time to assess the overall damage to Yellowstone’s infrastructure. The North entrance remains closed to non-commercial vehicle traffic, but is open to foot and bicycle traffic to Rescue Creek. The Northeast entrance also remains closed to non-commercial vehicle travel, but is open to foot and bicycle traffic in to Warm Creek Trailhead.

After careful consideration, the park reopened the south loop through the Park’s Southern Gate (North of Jackson Hole), East Gate (Cody), and West Gate (West Yellowstone), on Wednesday, June 22. As of July 2, the access to the north loop opened to the general public, allowing access the the majority of the National Park.

Entrance to the park through the South, East and West gates are open to all visitors at this time. We encourage all visitors to stay attuned to park road conditions and gate closures before planning any trips into Yellowstone.

We are devastated to see the damage caused by flooding in Yellowstone, and our hearts go out to the many communities reeling from this disaster. Interested in donating to Yellowstone and the communities directly affected by this disaster? Here are some options for disaster relief programs giving aid through this time.

If you’ve already booked your travel to Jackson Hole, consider the following activities for your trip.

Round off Your Summer in Jackson Hole

If you ask a “local” what brought them to Jackson, they’ll likely tell you it was Jackson’s epic and legendary free skiing. If you follow up with what kept them here, they’ll tell you emphatically: Summer in the Tetons. 

Late Summer Sunset over Mormon Row

Some take refuge on the cool, ribboning Snake River, casting flies, rafting, or braving the whitewater in river kayaks. Others seek meditative, soul-touching experiences in our mountains’ dramatic and awe-inspiring peaks. Regardless of your draw to the Tetons, there is something here for everyone.

The best part of your summer getaway doesn’t stop short in the mountains either. With just three (maybe four if we’re lucky) short months to take in all that summertime brings, there’s a fervent energy that draws in artists and musicians alike every year.

From July 3 through August 27, the Grand Teton Music Festival brings renowned musicians from across the country to perform in Teton Village. Check their calendar and be sure to book in advance of your visit.

Take in the exceptional spread from local and national artists featured at our annual Art Fair on August 5-7. From fine art to ceramics, paintings, furniture, photography, jewelry, and so much more, be sure to plan your trip to accommodate this wonderful event.

Pick up a pair of cowboy boots from the Town Square, and head to the rodeo for a real taste of the Wyoming dazzle. Be sure to book your tickets in advance as they do book out quickly.

And of course, there’s the Teton County Fair. With all the usual rides and games, our fair is a great way to have a good time alongside the local community. Check the schedule for daily events, and enjoy a quintessential summer night at the fairground.

Regardless of your preference for activities, there’s something here to not only please, but wow everyone in your group. End your summer on a high note, and book your Jackson Hole adventure today. You will not regret a moment spent here.

BROWSE AVAILABILITY

The Perfect Homebase for Your Summer Getaway

The skies have cleared, pushing out the cold, wet days of mud season and bringing forth days filled with sun and all that comes with summertime in Jackson Hole. From June until September, our valley is filled with reverie. Join the celebration of our countless summer activities, live outdoor concerts, farmers’ markets, and so much more by booking your summer getaway in the mountains. 

The Perfect Home Base for Your Summer Getaway

BROWSE AVAILABILITY

Spring Creek Ranch

Take in spectacular Teton views with an al fresco dinner at the quiet, private oasis at our Teton Retreat. Perched on the East Gros Ventre Butte, this spacious house features 4 bedrooms with ensuite bathrooms. Just a 12-minute drive from downtown Jackson, it’s the ideal home for a family vacation or trip with your favorite couples.

Take in the immense views of the Tetons as you unwind in the Mountain Tope Lodge hot tub placed right on its back deck. With 4 bedrooms, this custom log home is tucked away on the East Gros Ventre Butte, giving you privacy and solitude with a convenient 12-minute drive to downtown.

Westbank

Conveniently located between the town of Jackson and Jackson Hole Mountain Resort at Teton Village, our Westbank homes have you close to the action but separated from the crowds.

For a more intimate stay, our gorgeous Primrose 1715 condominium has 3 bedrooms and is the perfect option for a family. Enjoy warm summer evenings on the private patio and spend your days biking straight from the condo, utilizing our extensive bike path system that runs right past this charming Wilson neighborhood.

Just around the corner, our cozy Woodlands A5 unit features 3 bedrooms and 2.5 baths. Bask in the late summer sun on its private patio and grill up some delicious, freshly butchered meat from nearby Aspens Market just a quick walk away.

With 3 bedrooms and an external guest suite, our Wesbank home at Fish Creek 3725 is the ideal family getaway. Boasting a beautiful open floor plan with lots of natural light, and a sizeable private patio, this beautiful home has plenty of space for your whole family.

North of Town

Enjoy amazing sweeping views of the Teton mountains from our townhouse (D) in the Teton Shadows neighborhood. Conveniently located between the town of Jackson and Grand Teton National Park, this quiet neighborhood offers quick access to our national parks as well as our bustling downtown.

Another beautiful home located in the same area, with similarly spectacular views of the Tetons from its back deck, is our Golf Creek 41 home. Take advantage of your proximity to the beautiful hikes, swims, and the many other activities that Grand Teton National Park has to offer while staying in this charming oasis.

Downtown Jackson

Stay footsteps from the action of downtown Jackson at our One Town Hill 404 condo. At the base of Snow King Mountain, this modern, 3-bedroom condo has unparalleled access to all that Jackson has to offer.

Teton Village

Our Sleeping Indian E3 studio condo is the perfect spot for a romantic getaway. Take advantage of Jackson Hole Mountain Resort’s many beautiful hikes right from your doorstep. Cool down afterward in the Sundance swimming pool just across the street, and finish your day with an intimate happy hour for two on the deck.

Whether you’re looking to be in the heart of our festive summer crowds, or want a more secluded experience of the Teton Mountains, we have something for everyone. Don’t miss your chance to experience Jackson Hole this summer, and book your vacation in the last of the Old West today!

Best Personalized Experiences in Wyoming

Our innovative and welcoming team helps guests craft the best, personalized experiences for their Old West getaways. It’s truly no wonder that locals and tourists alike voted us gold in Best Property Management Company of JH in 2019, 2020, 2021, and 2022.  Let’s take a peek at some of Outpost’s exceptional personalized experiences and insider travel tips that make us the go-to for Jackson Hole, Wyoming vacations! 

A tour group in Wyoming

Treat yourself

Stay Outfitted with outdoor rentals, baby gear, florals, liquor, and so much more. All items are conveniently delivered pre-arrival. This personalized service is available exclusively to our guests and homeowners. Provisions, a sister company to Outpost, combines convenience and comfort all in one place. Guests have the option to book private chef dinners ($1000 minimum with advance notice), giving you a stress-free, relaxing and memorable food experience in the comfort of your rental. 

Delicious dining

Jackson Hole, Wyoming, is home to some exceptional restaurants. Be sure to make reservations! We don’t make them for you, but here are our recommendations for local dining: 

Activities abound in the valley! 

Again, we highly recommend you make reservations in advance. You and yours will undoubtedly have the best recreational experiences in all of Wyoming if you follow our insider’s list below: 

No reservations needed here

*For the outdoor enthusiast searching for something more off-the-beaten-path, this is a great hike in the Gros Ventre Mountains. Be sure to take a high clearance SUV as the road is rugged. Trust us, the views of the Tetons are well worth it! 

 

Jackson Hole Mountain Resort 

Guests love the newly expanded bike park, filled with trails for all experience levels. After a ride around the bike park, ride the tram or catch a gondola to Piste Mountain Bistro.  

Seeking some mindfulness? Enjoy yoga on the deck and salute the sun with expansive views over the Teton Valley! 

Get excited for spectacular views and adventures. You’ll make cherished memories for years to come. 

Shop Local: Support Local Business in Jackson Hole, WY

Can we let you in on a little secret? Believe it or not, there’s more to Jackson Hole than skiing. (Shocker, we know!) With a number of superb local businesses that cater to any and all shopping needs, no trip to Jackson Hole is complete without a local shopping spree. You heard it from us, it’s time to treat yourself! 

Begin your Jackson Hole shopping journey in historic Town Square and work your way up to the charming Teton Village. With our guided suggestions under your belt, that prickling itch to do some shopping will be scratched. Follow Outpost, and you’ll be shopping like a local in no time! 

Open sign at a local Jackson Hole shop

For The Best Local Souvenirs by Town: 

Town of Jackson

We love stopping by MADE for their artisanal handmade pieces, then heading over to their carefully curated Mountain Dandy on Pearl St., where shop collections boast a vintage masculine aesthetic. These two town favorites will add character to your Jackson Hole souvenir game. 

Teton Village

The G Store is your one-stop-shop for magnets, chains, keyrings, and more. Make sure to pick up an eclectic Provisions donut while you’re in there! 

Wilson

The talented team behind MADE and Mountain Dandy extends their community reach with M in Wilson. Grab a few eccentric stationery sets, custom totes, and tasteful home goods. 

For Outdoor Apparel: 

Get ready to take a shopping (and walking) tour of Jackson while visiting our favorite outfitters for outdoor apparel and gear. JD Highcountry and Skinny Skis have your skiing, hiking, and other recreational needs covered! No spree in town is complete without a stop at Stio, Jackson’s very own outdoor clothing line. When a local spots that pine logo, you’ll be sure to receive a nod of credibility.

For New and Vintage Western Gear: 

We have a soft spot for boutiques filled with quality western gear! Unearth timeless pieces at Womenfolk, a sophisticated consignment store, and JW Bennett, the go-to place for wearable works of art—and hats. Be sure to take a stroll through the infamous Pendleton for a classic flannel or memorable blanket to bring home the colors and textures of the West. 

For Your Boutique Needs

In search of something less western? Some boutiques we’ve fallen for include Altitude, Rodeo, and Roam. You’ll also find various shops, like Terra, sprinkled throughout downtown Jackson, Wilson, and Teton Village that are sure to fill your bag with fashion-forward items.

For Good Reads: 

Valley Bookstore is teeming with books about the area and from local authors, as well as a wide range of classics and new releases. Peel back the crisp cover of your new read after brunch at Cafe Genevieve right across the road! If you find yourself in Wilson, browse through Wilson Book Gallery while grabbing a coffee from Persephone Wesbank just next door. 

It can be difficult heading home after an enjoyable vacation, but this is your opportunity to take a piece of your Jackson Hole adventure back with you – you’ll leave these exceptional stores with bags (and hearts) full of unique goodies. Experience the last of the Old West your way – your mountain getaway awaits. Now, remember, this is our little secret (which we encourage you to readily share)! 

It’s nearly biking season in Jackson

Biking season is just around the corner! Jackson is a fantastic place for all kinds of biking! Enjoy road biking, gravel biking, or mountain biking – whatever your riding style, Jackson is the location for you. As the snow melts, we’re all looking forward to biking season being upon us once again.  

Scenic view from a biking trail in Jackson, WY.

Our favorite places for mountain biking 

Cache Creek Trail System

  • Incredible cross-country mountain biking
  • Easily accessible from the trailhead in East Jackson
  • Links up to Snow King Mountain – enjoy beautiful views of the Tetons and the Town of Jackson from your bike

Jackson Hole Mountain Resort (JHMR) Bike Park 

  • The bike park is open from June 11 to September 11 
  • Extensive lift access to downhill bike trails in Teton Village
  • Wonderful restaurants/Teton Village scene to enjoy after a day of biking

Targhee Bike Park 

  • The bike park will be opening in mid-June
  • Lift access to downhill bike trails
  • Beautiful cross country trails on the other side of the Tetons

Teton Pass

  • Exciting downhill and cross-country mountain biking trails
  • For experienced bikers – trust us

Our favorite places for road biking 

Bike Path from the Town of Jackson to Wilson –or- out to Teton Village

  • Stop along the way for a drink or snack in Wilson: 
  • Ride over the Snake River bridge, looking over the edge to try to spot the trout swimming below
  • Swing by R-Park and admire Thomas Dambo’s incredible Mama Mimi Troll

Bike Path from the Town of Jackson to Jenny Lake 

  • Expansive Teton views the entire ride out – keep an eye out for wildlife along the banks of the Hoback River and in the sagebrush
  • The scenic stretch of park road along the edge of Jenny Lake is breathtaking
  • Be mindful of traffic – the scenic detour along Jenny Lake is a shared road rather than a bike-only path

Local bike experts

Need a tune or rental? Check out some of the great stores in town for all your biking needs: 

And after a long day of biking, bask in the serenity of any one of our Outpost properties – your Jackson Hole home base!