The Benson Preferred Guide
Jackson Hole in Winter
Wyoming, United States
The Benson Preferred Guide to Jackson Hole, Wyoming (Winter)
Why Should You Visit Jackson Hole in the Winter?
If Jackson Hole in the summer feels like an adventure movie, Jackson Hole in the winter feels like you've stepped into a snow globe in the American West.
Growing up in Utah, both Diana and I spent our winters playing in the mountains. Skiing and snowboarding have been a part of our lives for as long as we can remember, so we're admittedly a little picky when it comes to mountain destinations. Jackson Hole is one of the few places that continues to impress us every single time we visit.
There is something special about waking up to fresh snow, spending the day carving through the mountains, and finishing the evening soaking in a hot tub while snow quietly falls around you.
Jackson Hole is one of those places that reminds us why we love winter.
Who Is Jackson Hole Perfect For?
Jackson Hole in the winter is perfect for:
- Skiers and snowboarders
- Couples looking for a cozy winter escape
- Families who love snow-filled adventures
- Snowmobiling enthusiasts
- Wildlife lovers
- Travelers who appreciate luxury mountain resorts
- Anyone looking for an authentic western winter experience
If your ideal winter vacation includes fresh powder, mountain views, and ending the day by a warm fire, Jackson Hole is hard to beat.
What Are the Best Things to Do in Jackson Hole in the Winter?
Some of our favorite winter experiences include:
- Snowboarding at Jackson Hole Mountain Resort
- Skiing throughout Teton Village
- Snowmobiling in Yellowstone National Park
- Riding in a horse-drawn sleigh through the National Elk Refuge
- Enjoying dinner and a western show at the Jackson Hole Playhouse
- Relaxing at the Four Seasons Jackson Hole
- Shopping and exploring downtown Jackson
- Taking in the mountain scenery after a fresh snowfall
One of the things we love most about Jackson Hole is that it doesn't feel overly commercialized. It still feels like a western mountain town that happens to have one of the most spectacular ski resorts in North America.
What Is Jackson Hole's Signature Winter Experience?
For us, it's snowboarding at Jackson Hole Mountain Resort.
I've been skiing my entire life but decided to make the switch to snowboarding a few years ago. Diana has been snowboarding for as long as I've known her, so she was more than happy to help me through my somewhat humbling transition.
Jackson Hole Mountain Resort has become one of our favorite places to ride because of its incredible terrain. The mountain is famous for its steep chutes, natural half pipes, bowls, and breathtaking views of the Tetons.
It's an absolute playground for intermediate and advanced riders.
If you're newer to skiing or snowboarding, I'd recommend looking at Snow King Mountain. It's a great place to build confidence without feeling intimidated by Jackson Hole's more advanced terrain.
Where Should You Stay in Jackson Hole?
The Four Seasons Jackson Hole is one of our favorite winter resorts anywhere.
There's nothing better than returning from a long day on the mountain, peeling off your snow gear, and climbing into the hot tub while watching snow fall over Teton Village.
The Four Seasons strikes a wonderful balance between luxury and mountain charm. The service is exceptional, the accommodations are beautiful, and the location couldn't be more convenient for enjoying everything Jackson Hole has to offer.
Some of our favorite moments in Jackson Hole have simply been slowing down and enjoying the resort itself.
When Is the Best Time to Visit Jackson Hole in the Winter?
- Peak Season: Late December through February offers excellent snow conditions and the full winter experience.
- Shoulder Season: Early March can be one of our favorite times to visit. The days are slightly longer, temperatures are more comfortable, and conditions are often still fantastic.
- Best For:
- Skiing & Snowboarding: January through March
- Snowmobiling: December through March
- Sleigh Rides: Winter months
- Resort Experiences: All winter season
- Families: February and early March
Insider's Secret
If your schedule allows, ski and snowboard during the middle of the week.
You'll spend less time waiting in lift lines and more time enjoying the mountain. The same goes for many of Jackson Hole's winter activities.
Jackson Hole is a destination that rewards slowing down. Don't feel like you need to fill every hour of your itinerary. Leave yourself time to enjoy the resort, grab a hot chocolate by the fire, or simply watch the snowfall outside your window.
What Is a Great 5-7 Night Itinerary for Jackson Hole?
- Day 1: Arrive and settle into the Four Seasons.
- Day 2: Snowboard or ski Jackson Hole Mountain Resort.
- Day 3: Snowmobile tour through Yellowstone National Park.
- Day 4: Relax at the resort and explore downtown Jackson.
- Day 5: Another day on the mountain.
- Day 6: Sleigh ride through the National Elk Refuge followed by dinner and a show at the Jackson Hole Playhouse.
- Day 7: Enjoy one final morning in the mountains before heading home.
Founder Favorite
Snowboarding Jackson Hole Mountain Resort together has become one of our favorite winter traditions.
There are few things better than spending an entire day exploring the mountain and then reliving your favorite runs over dinner that evening. Some of my favorite conversations with Diana have happened while riding chairlifts or warming up after a long day in the snow.
Jackson Hole has a way of making winter something to look forward to rather than simply endure.
Member Tip
Don't make Jackson Hole a ski trip.
Make it a Jackson Hole trip.
It's easy to fill your itinerary with skiing and snowboarding, but you'd miss so much of what makes this place special. Take time for the sleigh ride through the National Elk Refuge. Spend an evening at the Jackson Hole Playhouse. Explore downtown Jackson. Enjoy the resort.
The mountain will always be there tomorrow.
Our Favorite Experiences
One of the things we love most about Jackson Hole is that we're still discovering new experiences every time we visit. Granite Hot Springs is still on our list for an upcoming winter adventure, and I'm sure we'll continue adding to that list for years to come.
Jackson Hole has become one of our favorite places to embrace winter together. It's adventurous without feeling rushed, luxurious without feeling pretentious, and beautiful in every direction you look.
If you've ever wanted to experience winter in the American West at its finest, I can't think of many places I'd recommend before Jackson Hole.
Just don't blame us if you find yourself planning your next trip before this one is over.
Stay somewhere
worth remembering.
Be part of our private travel membership with hand-picked resorts and unforgettable experiences minus the hassle of timeshare or vacation home ownership.
We bought in so you don’t have to.
Simple, by design.
We personally travel the world finding extraordinary places and negotiating preferred-member access. You simply select which of them you’d like to experience too.
Members do three things.
Select your stay
Choose your destination and tell us the dates you have in mind.
We arrange it
We confirm availability and send your confirmation. You just show up.
Places that made the list.
Making memories and living life more fully.
Bull Sharks in Playa
They gather off this coast for a few months a year. Close enough to count the scars, calm enough to stay a while.
The walk at golden hour
Costa Rica’s Pacific coast empties out just as the light gets good. Most evenings, the beach is yours.
Hot chocolate at the bottom
The part of the day nobody photographs, and the part everybody ends up remembering.
First chair, fresh snow
Up the mountain before anyone else, on a morning that still has every track left in it.
And so much more…
Hosted personally by Paul & Diana Benson.
We're lifelong adventurers who believe travel is one of life's greatest investments. Not because of the places you'll go, but because of the memories you'll create and the people you'll share them with.
The Benson Preferred Guest List is simply our way of sharing some of our favorite places and experiences with our circle of friends, family, and people we're glad to know. Read more about our story →
Extraordinary places, the world over.
From Whistler to the Amalfi Coast, Niseko to Turks & Caicos · a growing collection of luxury resort destinations, hand-chosen and added as inventory opens.
Questions, answered
Is this a timeshare?
No. There’s no ownership interest, deed, points system, or long-term obligation · it’s a private membership for access to resort stays, and you can cancel anytime.
Is airfare included?
No. Members arrange and pay for their own flights and ground transportation.
Are you open to partnering with hotels, resorts, and other properties?
Yes — we’re always looking for distinguished, place-defining properties that meet our standard. If you represent a resort, boutique hotel, private residence, or unique experience, tell us about your property and we’ll be in touch.
Are resort fees included?
Your resort accommodation is covered. Any mandatory resort fees, meals, and local taxes are disclosed before you confirm a stay.
How long can I stay?
Request 3–7 nights. A full membership year covers up to a five-night stay for two; additional nights may be available based on inventory.
Can I bring more people?
Yes · add adults or children to your membership at signup or later. Your total party is limited by the accommodation’s capacity.
What if my preferred dates aren’t available?
Stays are subject to availability. We’ll suggest alternate dates or destinations to find something that works.
When can I book my stay?
Your dues prepay your stay night by night: a 3-night stay once you’ve paid about two-thirds of the year, four nights a little later, and the full five at a year (or prepay the year up front to book right away). Booking uses your one guaranteed stay for the year; additional stays may be available subject to availability.
Browse the properties.
The resorts available to members. New properties are added as inventory opens · join the list to be the first to know.
Choose how to begin.
Read the full Membership Terms & Disclosures before joining. Invitation-only, limited to founding members.
Guest List
- Free account · log in anytime
- Browse the collection & request stays for any open inventory
- No monthly dues · pay per trip when you book
- Upgrade to Priority whenever a membership opens up
Always free. Upgrade only if you want a guaranteed stay.
Solo Membership
- Priority access
- Luxury stay each year, for one (up to 5 nights)
- Book 3–7 night stays, subject to availability
- Priority Pricing on every stay
- Add a guest anytime · adults $50/mo, children 13 & under $25/mo
- 3% annual increase · cancel anytime · 3-day cooling-off period
Priority Membership
- Priority access
- Luxury stay each year, for TWO (up to 5 nights)
- Book 3–7 night stays, subject to availability
- Priority Pricing on every stay
- Add family at signup · adults $50/mo, children 13 & under $25/mo (adjust anytime)
- 3% annual increase · cancel anytime · 3-day cooling-off period
Envoy Membership
- Everything in Priority
- A guaranteed stay at a higher-end property — or 2–3 stays each year at our luxury destinations
- Envoy Pricing on every stay
- Add family · adults $50/mo, children 13 & under $25/mo
- 3% annual increase · cancel anytime · 3-day cooling-off period
Ambassador Membership
- Everything in Envoy, plus additional perks
- Up to one stay every month — or guaranteed stays at our highest-end properties
- Ambassador Pricing on every stay
- Add family · adults $50/mo, children 13 & under $25/mo
- 3% annual increase · cancel anytime · 3-day cooling-off period
Membership is limited · additional openings coming soon. Join the waitlist and we'll reach out the moment a place opens.
Request your stay.
Choose a property, room, and your dates. We'll check availability and confirm · you'll see the status under My Membership.
Stays are subject to availability. Specific resorts and dates are not guaranteed until approved.
Welcome back, Member.
Your requests
+ New requestLooking for somewhere specific that’s not in our current selection? Tell us where you want to go and when you’re looking — the Benson Concierge will get back to you as soon as possible with our best options.
Plan trips together
Build a multi-stop itinerary, split rooms with friends and family, and add activities everyone can see. Share your trip with one link.
Places worth writing about.
How you’d say it out loud. The web address comes from this.
Hold ⌘ or Ctrl for several. These become the “stays in this area” links on the guide.
This sets the voice. A guide that fakes a memory costs more trust than it earns clicks.
Optional, but this is the difference between a guide and filler. Nothing gets invented if you leave it blank.
For a guide you’ve already written. Your words go in exactly as pasted — nothing rewrites them. The AI only reads it, pulls out the metadata, and tells you how it would fare in AI search.
One per line. Or paste a spreadsheet with a header row for per-guide control:
destination,property,connection,note,focus,days
Quote any name with a comma in it — "Roatan, Bay Islands". Multi-value cells split on ;. Cap is 200.
For rows without their own. Leave it here — it’s the honest default for a long list.
Roughly 30–60 seconds each, one at a time. Close the tab if you like — progress is saved as it goes.
Things you and Diana already know. Every future guide for a destination inherits its memories automatically — say it once here and you never retype it.
In your own words, as you’d say it out loud. This gets quoted into future guides exactly as written.
Decides whether a future guide may write “we”.
Short form is fine — “Roatán” finds a guide called “Roatán, Bay Islands, Honduras”.
Leave blank if you or Diana said it. Filled in, the guide credits it instead of claiming it.
The “Follow our adventures” grid at the bottom of /our-story. Nine slots, three per row — fill three for one row, nine for three. Each tile shows your photo and opens the Instagram post it belongs to.
The timing layer. Pick a guide, say which months it is at its best, and give it the Benson Test. Guides with months set appear on /when-to-go and grow a timing block on their page. Leave months empty and nothing changes anywhere.
No guide yet — this creates a draft to hang the timing on. It becomes the guide when you write it, and shows on /when-to-go once published.
Paste a When-to-Go article (the Costa Rica format) and the sections below fill themselves. Nothing saves until you review and hit Save timing.
Loading…
The voice rules live here as text, not in code — change how every future guide reads without a deploy.
Placeholders: {{destination}} {{featured_property}} {{nearby_properties}} {{connection_context}} {{connection_note}} {{focus_areas}} {{word_count}} {{suggested_days}}
{{destination}} and {{connection_context}} are required — without them a guide has no subject or no voice rules.
All three required. A voice missing “going back after years” fails on the one guide that needs it most.
What’s working.
Where members come from · first touch
Attention by section
Most-viewed properties
The collection & partners.
Properties
Concierge Network
Partner inquiries · from /partner
Membership capacity
— of — memberships available · one per resort week held. (— members · — held off-membership.)