Why We
Do This.
Black Mountain Lookout · Sheridan, Wyoming
Unsolicited
Airbnb Alone
in Sheridan
I moved to Sheridan in March of 2007 for a railroad job. BNSF Conductor, running freight through some of the most beautiful country in the American West. I didn't plan to stay. Nobody really plans to stay in Sheridan — they just stop leaving.
My wife Kayla and I spent years traveling on Airbnb between 2012 and 2020. We loved it — the idea that a stranger's home could feel more like a place than a hotel ever could. When we bought a house with a garage — we wanted the garage — we didn't know what to do with the house. So we tried it ourselves. We closed January 31, 2020. The next few months were, as you might imagine, a crash course in everything.
That first property was The Troubadour Suite.
The Troubadour
Suite
Our first property. The one that started everything. Still in the portfolio, still personally hosted, still exactly what it was the day we opened it.
View & ReserveThe portfolio has grown from one to fifteen — a working ranch cabin, a 9,000 square foot historic department store on Main Street, two vintage Spartan trailers, a lux tack barn converted to a short-term rental, and everything in between. In 2025, we began co-hosting a small number of properties alongside owners who are just as particular about their homes as we are about ours.
1,247 reviews at 4.98 on Airbnb alone. We don't solicit reviews — we don't leave them for guests in hopes they'll return the favor. Every rating was left because someone wanted to. Whatever the total is across all platforms, we honestly stopped counting.
No other host in Sheridan can say that.
We used to operate under a different name — Sheridan's Best Stays. It was fine. Generic. Forgettable. We left it behind for something with a little more personality.
When we expanded beyond our own properties in 2025, our first co-hosting client was the most notable short-term rental in Sheridan.
The New York
Store Suite
Wyoming's largest department store from 1909. We co-host with owners who stay involved. They know and care for their property — we handle the hospitality.
View & ReserveTyler is working toward his Wyoming real estate license — a natural next step for someone who has spent five years thinking about nothing but Sheridan property. It won't change how we host. It'll just make it official.
Most of our family has since followed us to Sheridan from Billings. That probably tells you everything you need to know about the town.
— Tyler & Kayla Hert, Late Checkout WY
Kayla, her sisters,
and this town.
Kayla runs the day to day with her sisters at Real Deals — but Late Checkout is a family business that includes not only Kayla and Tyler, but Terry, Tyler's father, and Rhonda and Jason, Kayla's mother and stepfather.
We've made friends with more than a few guests over the years. People who come back every summer, who we meet for breakfast at Cowboy Cafe or a beer at The Mint. That doesn't happen by accident.
Real Deals on
Home Décor
& Boutique
Late Checkout WY is part of a broader investment in Sheridan. We own Real Deals, a home décor and boutique retail shop in downtown Sheridan. A lot of our guests end up there. Some of them come back the next year and go straight to the store before they check in.
"Be sure to visit their store, Real Deals on Home Decor in downtown Sheridan. They have adorable and fun gifts, clothing, and accessories for your home."
— Jody, Austin TX · Verified Airbnb GuestExtended holiday hours through December
A question
is a good start.
Booking questions, availability, co-hosting your property — or just wondering if Sheridan's actually as good as we say it is. We respond to everything personally.
Got it. We'll be in touch
before you know it.
"I love that everything I love that doesn't exist here, doesn't exist here. It gives me a reason to travel, to see something new, and to always come back excited about coming home."
— Tyler Hert · Sheridan resident since 2007