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I Took A 3-day, $3,700 Trip To Jackson Hole. This Is Exactly Where I Splurged And Saved.
The reporter splurged on hotels and saved on experiences during a three-day getaway to Jackson Hole.
Joey Hadden/Business Insider
- I took a three-day trip to Jackson Hole, Wyoming, that cost nearly $3,700.
- Luxury hotel stays and transportation were the priciest aspects of my trip.
- Traveling during shoulder season and spending nothing on experiences helped me save.
If there's anywhere to splurge on luxury travel, it's Jackson Hole, Wyoming.
The wealth enclave comprising Teton County is packed with top-tier resorts and wellness experiences, multimillion-dollar vacation homes, and elevated Western boutiques surrounded by mountains.
I took a three-day trip to Jackson Hole in September. Here's what it cost:
Transportation: $980 on rideshare services and round-trip flight tickets from NYC
Accommodation: $2,465 for two nights in upscale hotels and one night in a hostel
Food: $230
Activities: Free
While nearly $3,700 may sound steep for a short getaway, I could have easily doubled my budget had I not been conscious of how I spent — and when.
Looking back on the trip, I think I did a fine job balancing my budget by indulging in some areas at the expense of others.
I likely saved thousands by traveling in shoulder season.The reporter layered up during her September trip to Jackson Hole.
Joey Hadden/Business Insider
I began searching for hotel rates for my Jackson Hole trip in early August. Prices skyrocketed for winter dates at nearly every accommodation I considered, and flight costs doubled from mid-October to mid-November.
Teton County's peak seasons are summer and winter. Its proximity to Grand Teton and Yellowstone National Parks makes it a popular destination for hiking and skiing.
But I'm not a skier, so I thought a fall booking would help me stretch my budget as far as possible.
For those not interested in winter sports, I think the weather in September was ideal for spending time outside. With temperatures ranging from 40 to 60 degrees Fahrenheit, I was comfortable in two layers underneath a light jacket.
During this shoulder season of travel, there are fewer crowds than in peak visiting times, too, local real-estate agent Sam Haack told Business Insider.
For $980, I flew economy and used cabs to get around town.A view of Jackson Hole from the reporter's flight window.
Joey Hadden/Business Insider
On August 19, I booked round-trip flights from JFK Airport to Jackson Hole Airport (JAC) with American Airlines. The economy seats on connecting flights cost $650 with flight insurance.
My flight left NYC on September 16 — less than a month after booking. In hindsight, I should have snagged them a little sooner to potentially save more.
I spent $330 on seven rideshare cabs to get around town during the trip.
I spent my first night in one of the most expensive hotel rooms in town at an adults-only resort.Hotel Yellowstone, a resort in Jackson Hole.
Joey Hadden/Business Insider
More than anything else in Jackson Hole, I wanted to stay at Hotel Yellowstone.
The adults-only hotel overlooking the Tetons and Snake River Valley opened just a month before my stay. And the photos online were so alluring that I simply had to take my own.
The four-acre resort has 36 rooms with private balconies. Depending on the view, the starting rates range from $900 to $1,600 a night, a company representative told BI.
I wanted a room with unobstructed views of the valley and the Tetons, which incurred the highest price point — nearly double the average room rate across Jackson Hole that month.
A representative of Fora Advisor, a travel agency that works with hotels to provide perks for travelers, told BI that the average cost per night in Jackson Hole in September 2024 was $845.
Though BI received a media rate for the one-night stay, it was one of the most expensive hotel rooms in Jackson Hole and the highest bill on my trip.
So, I made the most of it.
It was worth the $1,600-a-night price for the best hotel stay of my life.Inside one of the most expensive hotel rooms in Jackson Hole at Hotel Yellowstone.
Joey Hadden/Business Insider
When it comes to luxury accommodations, I've been around. I've booked the top-rated resorts in Arizona and stayed in celebrity-loved hotels in Miami, Quebec City, and Milan.
After five years of sampling the finest accommodations in travel hot spots worldwide, Hotel Yellowstone still managed to wow me.
I was in awe of my room the moment I stepped inside. The space was designed to keep the mountains in view at every angle — from the bed to the bathtub.
I had a DIY spa experience in my room instead of booking a treatment.Inside the reporter's bathroom at Hotel Yellowstone.
Joey Hadden/Business Insider
When I stay at a luxury hotel, it's hard to resist booking a spa appointment. But they can take a good chunk out of your budget — some 40-minute treatments at Hotel Yellowstone cost more than $200.
Once I saw my Calacatta marble bathroom, I knew I wouldn't be giving in this time. The midcentury modern space had heated floors, towel warmers, a high-tech bidet, a roomy rainfall shower, and an oversize tub with a sliding door to view the mountains outside.
With a thick robe in the closet, I made my own spa day inside my hotel room. I set mood lighting using smart controls in my room, played calming music, and drew a bath with the sliding door open.
When it was time to dry off, I avoided goosebumps by wrapping myself in a warm towel as I stepped onto the heated marble floor. It was no massage, but afterward, I felt relaxed and refreshed.
Rather than spending more on cabs and activities, I spent my afternoon enjoying the hotel's views and complimentary amenities.The reporter's balcony view at Hotel Yellowstone.
Joey Hadden/Business Insider
The serene experience came with a high price tag, so I stayed on the Hotel Yellowstone property from check-in to check-out to make the most of my time there and avoid spending more money.
The hotel had a calming, heated pool and a wooden sauna that were free to use at all hours. But I spent most of the time in my room.
On my oversize balcony, I slouched into cozy seating and let the landscape provide most of my entertainment. During the day, I spotted a herd of cattle grazing the valley below. The hues on the mountain shifted through sunset, and at night, I had a faint view of the northern lights gliding across the sky.
I splurged on a $75 dinner because I knew my breakfast the next morning would be free.Two dishes at Olivia's inside Hotel Yellowstone's main building.
Joey Hadden/Business Insider
I had dinner at the most breathtaking restaurant I've ever been to — Olivia's, the guest-only restaurant beneath the lobby of Hotel Yellowstone. The room had a marble bar and floor-to-ceiling windows covering two walls. It felt like dining outside without enduring the elements.
Olivia's was an eclectic restaurant serving local ingredients. Since my hotel stay included complimentary breakfast, I decided to go all-out on dinner. I spent about $75, including tip, on short rib bao buns, Toffee pudding with cinnamon butter gelato, and a nostalgic Shirley Temple.
The next morning, my steel-cut oats and coffee were complimentary — and so was the moose sighting right outside the window.
After checking out, I went downtown to check out the square and surrounding streets.The town square in Jackson, Wyoming.
Joey Hadden/Business Insider
Day one was an expensive night, so on the morning of day two, I needed a free activity. I took a cab to Downtown Jackson to window shop and people-watch.
I started in the town square, a small park with antler-arched entryways. Children danced as street performers played guitars.
I found public art on every corner. Sculptures of horses and cowboys paired with Old Western-inspired architecture made me feel like I was in an outdoor museum.
I wandered stores to gather inspiration instead of actively consuming.A Western boutique in Downtown Jackson.
Joey Hadden/Business Insider
The streets surrounding the square were lined with shops and restaurants. The cowboy culture was in full swing as I passed Western apparel boutiques and rustic, chic furniture stores.
While wandering these blocks, I didn't take out my wallet once. Instead, I simply gathered inspiration. At clothing stores, I paid attention to how layers were arranged and draped over mannequins. In furniture stores, I searched for unique color palettes and decorative arrangements.
When I found something I liked, I snapped a picture for future reference.
Then, I had an upscale lunch that cost about $35.House-pulled mozzarella at Bin 22 in Jackson, Wyoming.
Joey Hadden/Business Insider
To save on food, I fueled up during breakfast so I could wait until late afternoon to eat lunch or early dinner. I went to Bin 22, a tapas restaurant with a wine shop and specialty grocer inside. My lunch cost about $35, but it tasted more expensive.
To start, I had a house-pulled mozzarella appetizer with sea salt and balsamic glaze. Paired with toasted bread, it was simple and delicious. And the mozzarella tasted so fresh that I couldn't believe I was in Wyoming and not New York or Italy.
I enjoyed my main course even more. The avocado lentil salad was impeccably balanced with a refreshing lemon-garlic aioli.
With a full stomach, I headed to my second hotel — the five-star Four Seasons Jackson Hole resort.The Four Seasons Jackson Hole, a five-star resort in Teton Village.
Courtesy of Four Seasons Jackson Hole
After a day well spent in Downtown Jackson, I headed to Teton Village, one of the most expensive neighborhoods in Jackson Hole, where the Four Seasons is located.
I booked a guest room with a balcony, which had a starting price of $715 a night at the time of booking, though BI received a media rate for the one-night stay.
It was my first time staying at the luxury hotel chain, and I was surprised when a Four Seasons representative told me that each location is uniquely designed to serve the destination. She said the Four Seasons Jackson Hole went for a "modern mountain chic" — and I think it delivered.
For $715 per night, my room had a luxury cabin feel.A peek inside the reporter's room at the Four Seasons Jackson Hole.
Joey Hadden/Business Insider
My 550-square-foot room was a place where midcentury modern luxury met Western interior design. It had a magnificent king-sized bed, a roomy marble bathroom, a gas fireplace, and plush, cozy seating. At the back of the room was a small balcony with views of Rendezvous Mountain.
The room was less impressive than the Hotel Yellowstone room, and the view was less dramatic. But I thought it had a great value for a significantly lower price point.
My breakfast at the hotel's Westbank Grill cost about $50.Avocado toast and orange juice at the Four Seasons Jackson Hole.
Joey Hadden/Business Insider
Before checking out on the morning of day three, I headed downstairs for breakfast at Westbank Grill. Although my booking didn't include a complimentary meal, I appreciated that I could grab a bite at this restaurant inside the hotel.
Like all the food I'd had on my trip, I felt fueled by fresh-tasting ingredients. I started with freshly squeezed orange juice with a perfectly balanced sweet-tart flavor.
For my meal, I had multigrain avocado toast stacked with burrata, marinated heirloom tomatoes, and crispy asparagus. It was paired with a small salad and a poached egg.
Avocado toast is my go-to item on breakfast menus, and this one had a greater variety of texture and flavor than most I've tried.
I spent my final night in a hostel for $150 a night.The entrance to Cache House in Downtown Jackson Hole.
Joey Hadden/Business Insider
After two lavish and expensive nights, I budgeted my trip with the cheapest accommodation I could find — a $150-a-night, queen-sized bunk in a hostel.
Although booking this stay allowed me to splurge on my other two hotels, I was a bit nervous about a drastic shift in comfort and privacy — especially since I'd never stayed in a hostel before.
Upon arrival, I quickly learned that even the hostels in Jackson Hole have an upscale vibe. Cache House is designed to elevate the typical European hostel experience.
Once I stepped inside, I knew I had nothing to worry about.
Surprisingly enough, the hostel had its own brand of luxury.The reporter's bunk at Cache House, an upscale hostel.
Joey Hadden/Business Insider
The hostel was located in the basement of the Anvil Hotel. Inside, it was clean and modern with a touch of Western flair. There was a spacious communal space, a large bathroom with private shower and toilet stalls, high-end toiletries, and locked storage spaces.
I intentionally booked my low-budget stay on the final night because I thought I might not sleep as well and would be able to nap on the plane ride home. But thanks to a night of deep sleep, I was awake the whole way back to NYC.
When I sat on the bed in my top bunk, I didn't want to get up. Like my other two stays, the mattress was firm with just enough give. And wool bedding made it just as cozy.
I also credit my good night's rest to the unexpected level of privacy. My bunk felt like a secluded nook with light and soundproof curtains. I slept for eight hours, which is more rest than I normally get at home.
I spent the rest of the afternoon acquainting myself with the walkable neighborhood.A street in Jackson, Wyoming, near Cache House.
Joey Hadden/Business Insider
Although Cache House didn't have the resort amenities of my other stays, it was located in the walkable downtown area, so there was plenty to see and do.
Since I'd already spent so much time walking around, I realized I had gotten to know the streets. I was able to navigate downtown without using Google Maps.
I was impressed with myself for truly getting a feel for the town in such a short time.
After exploring more of Downtown Jackson, I spent $63 at a fine-dining establishment.A weekly special fried chicken dish at the Bistro in Jackson, Wyoming.
Joey Hadden/Business Insider
While perusing storefronts, I spotted the Bistro, a restaurant run by the same company as Bin 22. Since I enjoyed my lunch the day before, I decided on the local fine-dining spot for my final meal of the trip.
It was probably the least healthy meal I had in Jackson Hole, but it was worth it. I started my meal with a sparkling, non-alcoholic rosé, which tingled my palette for the main event — the weekly special.
It was a fried chicken dish with buttery mashed potatoes and corn on the cob. The chicken was everything I wanted it to be — crispy, tender, and rich in flavor. The portion was generous for a fine-dining restaurant in my experience. It came with a thigh, a breast, and a drumstick.
I spent $63, including tip, on this filling dinner, and I wish I could have finished it all.
On my morning flight home, I reflected on my spending and was proud to find the ideal balance of luxury and frugality.The reporter in her room at Hotel Yellowstone.
Joey Hadden/Business Insider
Booking my trip during shoulder season, diversifying accommodation types, and opting for free activities allowed me to stretch my money far. And I'll use the same budget model for future getaways.
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