Outpost Jackson Hole

Vacation Rentals in Jackson Hole

Jackson Hole Winter 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. 

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)! 

Insider’s Guide to the Rendezvous Mountain Festival

Springtime in Jackson Hole just got better, with the return of the iconic Rendezvous Mountain Festival. After a two-year hiatus, our beloved spring music festival returns for its seventh season, ushering in spirited headliners, amicable crowds, and good vibes all around. Join us over at Outpost for two thrilling days of free concerts, and exciting spring skiing. Make sure to book your life tickets well in advance. You’ll be more than prepared to say “Goodbye Winter, Hello Spring,” alongside visitors and others in the local community, with our insider’s guide to the Jackson Hole Rendezvous Mountain Festival. 

An event flyer for the Rendezvous Mountain Music Festival, in Jackson Hole, WY.

Rendezvous Mountain Festival Line-Up 

The biggest music fling in town returns April 1-2, 2022, set against the picturesque backdrops of Jackson Hole Mountain Resort and historic Town Square. Every year, this free outdoor festival draws in legendary music acts, like Portugal. The Man and Nathaniel Rateliff & The Night Sweats. We’re so excited to introduce (and watch) this year’s talented line-up! 

Friday, April 1

Multi-platinum Fitz and The Tantrums will open the festival in Town Square, supported by folk singer Brett Dennen! Both artists have established themselves as hit-makers, consistently leaving their mark on the music industry. We guarantee that their feel-good jams will send cheerful ripples through your soul, warming you from your snow boots to your beanie. 

Gates open at 5 p.m. 

Saturday, April 2

Catch a passionate and soulful performance on Saturday by Ben Harper & The Innocent Criminals, multi-instrumental Grammy-winning musicians weaving together reggae, rock, blues, and soul genres. Supporting bands Cold War Kids and The Wailers carry their own impressive merits as global festival circuit staples. You don’t want to miss this undoubtedly memorable penultimate show! 

Gates open at 4 p.m.

Free general admission is first-come, first-serve, with optional paid VIP tickets available.

Come As You Are

Rendezvous Mountain Festival brings together the best of both worlds: great music and spring skiing. Remember to book your lift tickets well in advance. Come as you are every festival night, straight from the slopes, and seamlessly blend into the sea of locals and out-of-towners. You already know where to find us locals this festival season—skiing during the day and enjoying stellar concerts in the evenings!

Stay near the Festival 

Get festival ready by staying in one of our Teton Village and Town of Jackson rentals located near both event locations. These festival outposts grant you access to authentic mountain living and desired proximity to all spring concerts. See you this spring for the ultimate Jackson Hole rendezvous! 

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.

Tired of Winter? Set Your Summer Plans with Outpost Now

Outpost is accepting summer reservations, just in time for all of us looking forward to warmer days. Start shaking off the winter blues and secure your summer plans now. We know all the odds and ends of the Jackson Hole valley and are here to help you enjoy the last of the Old West. 

Grand Teton, a wonderful Wyoming staple, is pictured during a summer with Outpost.

Wyoming summers are one-of-a-kind, and we’re grateful to be in the heart of all the action, located near beautiful Grand Teton National Park. With over 200 properties to choose from, there’s a summer home for everyone at Outpost. However, vacation rental planning is just one piece of the larger vacation experience puzzle. There’s no vacation without worthwhile activities! Many in-demand Grand Teton summer activities need to be booked in advance, so let’s get started—

Guided Fly Fishing 

Access all the major rivers in the Jackson Hole area when you enjoy a guided fishing trip with Fish The Fly Guide Service. The talented guides can cater to any ability level, from novice to expert. It’s a fun summer activity that takes you to scenic places around Grand Teton. 

Sunrise Scenic Float

Kick your feet up and meander on the park’s Snake River during a scenic float trip! Get an early start, cruising about as the sun rises, setting the sky ablaze with gorgeous reds, oranges, and yellows. Keep your eyes peeled for some of the incredible wildlife that lives in the valley – animals are frequently seen along the riverbank at this time of day. We recommend booking with Dave Hansen or Solitude. 

Sunset Wildlife Safari with EcoTours

Here at Outpost, we cherish Jackson Hole’s diverse wildlife and encourage our guests to experience it for themselves. Bask in the glorious Grand Teton ecosystem with an EcoTours Sunset Wildlife Safari. You’ll drive around the backroads, avoiding summer crowds, and be treated to uninterrupted observation of wildlife, from moose and elk to grizzly bears and bison. 

Teton Views from Your Jackson Vacation Rental 

Even when you’re not physically in Grand Teton National Park, our rentals in the Town of Jackson and North of Town boast stunning Teton Views. Grab a fresh cup of coffee and feel the rising sun on the back of your neck as you stand on your spacious private mountain-facing patio. Outpost has the perfect summer home bases available for reservations today! 

Outpost’s Summer Quick Tips:

 
Road Closures 
  • Grand Teton National Park’s Granite Entrance park road will be closed during the summer of 2022 for maintenance. For visitors staying in Teton Village, please be aware that you will need to drive through the town of Jackson to access the park. 
  • If you’re coming in early summer, please note that the Jackson Hole Airport is closed April 11th – June 27th. Shuttles are available from Salt Lake City, UT, and Idaho Falls, ID, or you can enjoy a road trip out here.
Restaurant Reservations

Make sure to book restaurant reservations in advance, too! Check Resy/Open Table six to eight weeks before your vacation. We love the outdoor dining at Orsetto and Roadhouse Brewery in the Town of Jackson. Calico in Wilson is another favorite of ours. Wyoming summer nights are cool, so don’t forget a jacket!

3 Spacious Jackson Hole Homes for Safe Travels

With spring and summer right around the corner, many of us are searching for the perfect family or group vacation while navigating the current travel environment. Outpost has a beautiful portfolio of vacation rentals, ranging in size from cozy condos to luxurious and spacious family homes.

Outpost is dedicated to providing guests with safe accommodations during this pandemic. Our thoroughly sanitized Jackson Hole luxury vacation home collection suits large groups seeking space! You can enjoy the finer things in life, from lavish furnishings to incredible mountain views. Our guests book with confidence, knowing we take all the proper precautions prior to your upcoming visit. Keep reading for more details on the three featured Jackson Hole homes for large groups—

Granite Creek Escape

One of our largest western-style homes, you and 23 other guests can sleep comfortably in Granite Creek Escape. This ski-in/ski-out eight-bedroom home allows large groups to get away from the bustle of Jackson Hole, WY. Gather around the fireplace, hot tub, or large kitchen island with those you love. 

Holly Drive Homestead

This rustic single-family home is ideal for multi-family groups looking for a chance to spread out! Everyone will have their own little space at Holly Drive Homestead, which sleeps up to 14 guests. You will still be within close proximity of all activities in Teton Village while feeling removed from it all.

Shooting Star Lodge 7

Get prepared to feel incredibly cozy in this luxury family home that can sleep up to 10 people and features an extensive array of amenities. You and yours can relax in the private hot tub, by the gas/wood fireplaces, and at the stove in your very own gourmet kitchen! It’s perfectly suited for those needing a warming, luxurious retreat after a day out on the mountain.

Gain Peace of Mind by Staying with Outpost

Book your spring family home with Outpost online today! When you book directly on our site, you can save between six to twelve percent of the total price, avoiding exorbitant third-party service fees. Please read more about our commitment to your Jackson Hole travel health and safety here.

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!