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Jackson Hole Vacation Rentals



The luxury Jackson Hole properties in Annie’s collection are perfectly designed for comfort, luxury, and convenience. You’ll find everything from sprawling chateaus with panoramic views of the Teton Mountains to dreamy ski-in/ski-out homes with backyards full of fresh powder. Whether brand new modern chalet, true on-mountain retreat, or custom log home in a peaceful resort community, you can expect the same high-end finishes and luxury amenities in each Outpost.

In spacious great rooms with cathedral ceilings, sink into luxe sofas in front of a cozy wood-burning fireplace while floor-to-ceiling windows offer panoramic views. Expansive primary suites boast stone fireplaces, handcrafted log furniture, steam showers, soaking tubs, and heated floors, while thoughtfully-designed kids’ rooms feature bean bag chairs, games, road rugs, and custom built-in bunks families will love.

In Annie’s collection, incredible amenities come with the territory. Fireplaces in bedroom suites, handcrafted log furnishings, scenic views, on-property hiking trails, wet and dry bars, gourmet kitchens, mud rooms with heated floors, custom ski storage, exercise rooms, Sonos sound systems, heated garages, billiards tables, saunas, media rooms, and more. 

Private hot tubs with endless mountain and valley views, outdoor kitchens, and private patios nestled in the trees maximize the surrounding landscape and invite guests to immerse themselves in nature. Stroll to Teton Village, walk a few steps to the lift, or ski in and out from your luxury mountain retreat.

Doyenne of Outpost

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Annie Jackson
Managing Director
Favorite Restaurants
King Sushi, Snake River Grill
Favorite Bar
Million Dollar Cowboy Bar
Favorite Coffee
Snake River Roasting Company
Favorite Places to Shop
Habits, Mountain Dandy
Favorite Hike
Table Mountain
Favorite Things to Do in Jackson Hole
Skiing, trail running, and summer days spent on the Snake River

Annie Jackson, as the Managing Director, spearheads the committed and locally-based Outpost team, driven by a mission to deliver unparalleled service, attention, and respect to both guests and homeowners. The company takes immense pride in its distinctive culture, which places a paramount focus on prioritizing employees' well-being, motivating them to consistently exceed expectations in all their endeavors.

At Outpost, what began as a single home in 2014, has grown to be the premier vacation rental company in Jackson, voted Best Property Management Company for five consecutive years. Within their inventory of 250 properties (and counting) – a third of the professionally-managed homes in the area – Outpost strives to be a home base for everyone, from young couples saving up for a weekend away to ultra-luxe homes for discerning guests.

With the goal of always providing a best-in-class experience, Annie’s team values and nurtures partnerships within the Jackson Hole community, providing a tremendous benefit to guests and homeowners. From a partnership with JH Air that enables seamless delivery of lift tickets to facilitating gear rentals, organizing private chefs, and welcoming guests with their own coffee and handmade donut holes, Annie’s team provides the warmest welcome to every single guest.

Through its portfolio of local businesses, Outpost extends beyond vacation rentals to include cleaning, landscaping, snow removal, coffee roasting, catering, private chefs, and a cafe – brands that truly set them apart. While each business thrives on its own, they also support one another to ensure guests, homeowners, customers, clients, and partners all have a unique and memorable experience in Jackson Hole.

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