Jackson Hole Vacation Rentals
byOutpost
Annie's rental homes offer a great mix of comfort, luxury, and convenience for your stay in Jackson Hole. Book a stay in a large chateau with views of the Teton Mountains or a cozy ski-in/ski-out home with a yard filled with fresh powder. Each property in the Outpost portfolio promises high-end finishes and luxurious amenities. Staying in a modern chalet or custom log cabin nestled in peaceful resort communities will enhance your stay in Jackson Hole.
Step into spacious great rooms featuring cathedral ceilings, where you can relax on plush sofas by a cozy wood-burning fireplace while floor-to-ceiling windows showcase stunning mountain views. The large primary suites are designed to be comfortable places for relaxation. They feature stone fireplaces, handcrafted log furniture, steam showers, soaking tubs, and heated floors. Families will feel welcome, as there are kid-friendly rooms with bean bag chairs, games, road rugs, and custom-built bunk beds, helping young ones feel at home.
In addition to their spacious layouts, each home in Annie’s collection comes equipped with premium amenities that bring an extra layer of indulgence to your stay. Fireplaces in bedroom suites, gourmet kitchens with high-end appliances, wet and dry bars, custom ski storage, heated mudrooms, and private hot tubs overlooking sweeping mountain and valley views meet every guest’s needs. Thoughtfully designed details elevate your experience, whether you’re enjoying a family vacation or a romantic retreat.
Some homes offer outdoor kitchens and private patios, perfect for immersing yourself in nature. Additional features like Sonos sound systems, media rooms, billiards tables, saunas, and heated garages elevate your stay. On-property hiking trails and exercise rooms cater to the active traveler.
Beyond the comforts of your luxury retreat, exploring the area is a memorable experience. Take a walk to Teton Village or visit the nearby town of Jackson. In Jackson, you can see Snow King Mountain, the National Elk Refuge, and the famous Town Square.
For outdoor enthusiasts, Yellowstone National Park is a less than 3-hour drive away, offering endless adventures and natural wonders. Whether you’re seeking the thrill of skiing or the serenity of nature, your stay with Outpost promises the perfect balance of relaxation and exploration. This collection of Jackson Hole lodging is conveniently reached via the Jackson Hole Airport.
Browse the Collection
Doyenne of Outpost
Annie Jackson
Favorite Restaurants
King Sushi, Snake River GrillFavorite Bar
Million Dollar Cowboy BarFavorite Coffee
Snake River Roasting CompanyFavorite Places to Shop
Habits, Mountain DandyFavorite Hike
Table MountainFavorite Things to Do in Jackson Hole
Skiing, trail running, and summer days spent on the Snake RiverAnnie Jackson, as the Managing Director of Outpost, leads a passionate, locally-based team focused on delivering unparalleled service and attention to guests and homeowners. Outpost focuses on employee well-being and professional growth. This creates a motivated team that is eager to go the extra mile in every interaction. Jackson Hole recognizes Outpost as its premier vacation rental company for its dedication to excellence and reliability.
Outpost started as a single property in 2014 and has since expanded to become Jackson Hole’s premier vacation rental company, with 250 properties comprising nearly a third of professionally managed Jackson Hole vacation homes. Outpost offers a variety of properties, from cozy mountain cabins to luxury estates.
They cater to different guests, including families and those looking for a high-end experience in Jackson. Voted Best Property Management Company for five years in a row, Outpost provides a welcoming home base for everyone. Whether you're a young couple on a weekend getaway or a family looking for a luxury stay, we have one of Jackson’s finest properties for you.
Annie’s team thrives on strong partnerships within the Jackson Hole community. Collaborations with organizations like JH Air simplify travel logistics, offering guests the convenience of having lift tickets, gear rentals, and other essentials ready upon arrival. These partnerships extend to arranging private chefs, personal shopping, guided experiences, and curated events for guests, setting Outpost apart in personalized guest services. Each guest receives a warm, unique welcome, from handmade donuts and locally roasted coffee to thoughtfully curated amenities that capture the spirit of Jackson Hole.
Beyond managing vacation rentals, Outpost has grown a diverse portfolio of local businesses, offering services from cleaning, landscaping, and snow removal to coffee roasting, catering, private chef services, and even a café. Each brand complements the others, creating a cohesive ecosystem that ensures guests, homeowners, clients, and community members alike enjoy a memorable experience in Jackson Hole.
One of the most iconic ski destinations in the country, Jackson, Wyoming exudes laidback luxury throughout its scenic mountain town, challenging powder-covered slopes, and stunning scenery. In this peaceful haven, unwind in natural hot springs, take your tastebuds on an adventure with world-class dining, hike through wildflower-covered fields, get your thrills paragliding, rock climbing, and mountain biking, and view grizzly bears, bison, and moose in nearby Grand Teton National Park and Yellowstone.
These are just some of the reasons Annie Jackson, Managing Director of Outpost, loves Jackson Hole.
