Vacation Rentals in Jackson Hole

Come ski the last of the Old West this Winter! We can help you find a place to stay and bundle lift tickets along with it for additional savings. With over 200 properties to choose from, we have something for everyone.

Savings Tip: Did You Know?

You can save between six and twelve percent of the total price when opting to book directly through our site. AirBnB and Vrbo charge high service fees.

Join Our Portfolio

Outpost couples exemplary service with exceptional performance. Get to know Outpost: a boutique firm powered by a great crew and innovative company culture. We are only five years old but have quickly become the largest vacation rental company in the valley.

Discounted Lift Tickets with Lodging

Save on lift tickets when you package them with lodging. Simply choose a listing, select your winter dates, and a pop up will appear for you to add tickets and measure your savings. We even deliver the tickets to have them waiting in your rental home upon arrival!

Grocery and Liquor Delivery

Available exclusively to our Outpost guests and homeowners, we offer grocery delivery service and liquor delivery (through a licensed liquor vendor). Visit out Outfitted page.

Trip Insurance

Travel insurance helps protect your trip in the case the unexpected happens. With Winter coming, make sure weather doesn’t put a damper on your trip. Choose to cover your vacation with travel insurance.

Explore Rentals by Area

Explore the different areas and complexes of Jackson Hole by visiting our “Areas” page. We feature many condos in One Town Hill, Crystal Springs, Grand View, and more! We also have different areas in which you can select single family homes.

Browse By Area
One Town Hill

We are very happy to offer 18 One Town Hill luxury condos as vacation rentals. Enjoy the serenity of being steps away from trails while also being walking distance to Town Square.

Baby Gear & Outdoor Item Rentals

We rent out baby gear, household items, and outdoor gear exclusively to our Outpost homeowners and guests. We deliver these items to you prior to checking in and will remove them upon checkout!

Simply visit our Outfitted site!

Luxury Collection

From lavish hot tubs to slope side pied-a-terres, we have a great selection of properties that will check all the boxes on your list.

O2 Cleaning: Did You Know?

Our sister company, O2 Cleaning, employs upwards of 35 housekeepers. Not only do we clean for all the homes we have in our portfolio, but also homes around the valley.

Featured Properties with Private Hot Tubs

Have a question? Please call us! We are happy to help.

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