How To Spend a Perfect Weekend in Jackson Hole — From Hat Making To Dogsledding at the Base of the Teton Mountains

It came as no surprise when I recently learned that Texas is one of Vrbo’s biggest markets. Texans *love* a big house in a fabulous location. For my own adult spring break, I recently traveled to Jackson Hole, Wyoming, where I stayed in one of Vrbo’s 2025 Vacation Rentals of the Year.

Today, Vrbo revealed their 2025 Vacation Rentals of the Year. The annual list names 10 standout private vacation rentals across the United States and includes one Texas property on this year’s list — a nine-bedroom house in Dripping Springs with an “entertainment barn” where a truly epic fantasy football draft ought to take place. Additional honorees include everything from a mansion on 30A in Seagrove Beach, Florida (perfect for a girls’ weekend) to a serene A-frame in Bethel, Maine to a six-bedroom home on the beach in Saugatuck, Michigan. (The host notes that if you book for seven days in the summer, they’ll throw in a “complimentary four-hour trip on [their] yacht.”) “Villa Fabulosa” in Temecula, California’s wine country, accommodates 24 guests and even includes an 18-hole mini golf course. And located in Teton Village, the 6,200-square-foot Jackson Hole chalet known as “Under the Tram” allowed me to live the aprés-ski life I always imagined for myself for one weekend.

Under the Tram

Conveniently located under Aerial Tram, the Vrbo house offers ski-in, ski-out access. While I do not ski, I love anything and everything that comes before and after skiing, which is why the aprés life is the life for me.

In addition to four supremely appointed bedrooms (featuring luxurious linens and bathrooms with heated floors!), the home boasts a private sauna and hot tub for guests to enjoy after a long day of skiing.

Our hosts planned a truly perfect weekend, and I would be doing a great disservice to you, dear PaperCity readers, if I did not share highlights of the incredibly well-researched and curated itinerary from this magical long weekend in Jackson Hole.

Dining In Style in Jackson Hole

Under the Tram boasted a true chef’s kitchen, and we made the most of it! On both Friday and Sunday nights, we hired private chefs — Chef Tom Holle and Chef Andrew Blake, respectively — to cook dinner for us in the house. There is something so luxurious about enjoying a chef-prepared, multi-course dinner at home while wearing your coziest socks under the dining table. Favorite local dishes I spotted on almost every menu included grilled bread topped with local mushrooms, bacon-wrapped dates with goat cheese, and Rocky Mountain lamb chops. On Sunday night, Chef Andrew Blake, who is a bit of a celebrity with an Instagram following of more than 133,000, prepared an exquisite dinner that included a mushroom flatbread, beet salad, chicken marsala, and blueberry creme brûlée.

On Saturday night, we dined at Local. (Fittingly, every local said it was their favorite restaurant in town.) I also enjoyed riding the gondola alongside the skiers to the top of the mountain for a bowl of bison chili at Piste Mountain Bistro, having a drink on the saddles at Million Dollar Cowboy Bar (a honkeytonk that has been slinging cocktails since 1937), and enjoying a latte and croissant from Persephone Bakery.

The Full Drip

To stay hydrated and adjust to the altitude in Jackson Hole, we received custom drips from House Call Hydration, a mobile IV therapy service, on the first morning of our trip. Because I am middle-aged, I selected an anti-inflammatory just, like, preventatively. Sitting around the fireplace enjoying a toasted piece of sourdough while starting your mountain trip off with an in-home IV with your gal pals? Sign me up.

Tipping My Hat

Making a custom hat at Encounter Hat Co., conveniently located in Jackson Hole’s town square, stood out as my favorite part of the entire trip. As a native Texan and seasoned Round Topper, I’m used to the ol’ hat trick tourist trap. I anticipated a gimmicky store where we selected a feather or two, branded our initials into the felt, and called it a day… to the tune of $1,200. Instead, Alexandra at Encounter led us through our appointments with knowledge and a meticulous attention to detail. All the hats start out exactly the same, tabula rasa. Alexandra then molded the hat to each individual’s head. She trimmed the width to our exact preferences; she even customized the hat’s crease! For the four in our party, the experience took a little more than three hours. We all selected grosgrain ribbons and hat bands to adorn our toppers, forgoing feathers, charms, or brandishing our initials. Our hats cost around $650 each. Similar companies offer far less and charge double. Even my travel companions from New York delighted in the Western experience and wore their hats on the plane home!

Texans will also want to make a pilgrimage to Lela Rose Ranch. The Texan’s charming Jackson Hole outpost offers a curation of both new and vintage Western goods sourced by Rose herself.

Jackson Hole’s Call of the WYld

Another indisputable highlight? Dogsledding at the base of the Teton Mountains. On Sunday afternoon, we cozied up in a couple of two-person sleds for a picturesque one-hour dogsledding tour with Call of the WYld. Before the tour began, the guide invited us to pet the dogs (you don’t have to ask me twice!). As an animal lover and mother to a spoiled Standard Poodle, I asked a lot of questions and ensured all the dogs enjoyed their jobs. Shonny, for example, wasn’t in the mood to work but *was* accepting belly rubs. Anatoli, a Greenland Huskie, captivated me with her regal coat. She prefers the coldest of cold days. Apparently, a lot goes into the anatomy of a dog team (“Brains in the front. Brawn in the back!”). Mid-tour, our two sleds even traded a few dogs to more equitably distribute the talent. Skimming the snow behind these magnificent creatures thrilled me; I will remember the experience forever.

Throughout the weekend, locals said, “If you think it’s beautiful now, just wait until you see Jackson Hole in the summer!” For due diligence as a journalist, I think I need to return this summer. I’m very committed to my reporting. And I need a summer hat!