Jackson Hole

Jackson Hole Vacation Rentals


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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.


Price Range
Private Hot Tubs

The 100 Collection of Outpost

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.

Vacation rental in Jackson Hole
Majestic views from a Jackson Hole vacation rentalMountain views from a Jackson Hole vacation rental
Services Offered
  • 24/7 Guest services
  • Baby gear rentals
Services Available
  • Outdoor gear delivery
  • Grocery delivery
  • Private chefs & catering
  • Lift ticket & ski rentals through Outpost
Doyen of Outpost
Profile picture for Annie Jackson
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.