(#1) Cabin Chronicles: Why We Bought a Yellowstone Fixer Upper

cabin chronicles

Mar 31

Written By Kelly W

On a whim in October 2023, we stopped by a property in Gardiner, Montana, located just a stone’s throw from Yellowstone National Park. At first glance, the place was rough. Unfinished projects, exposed wiring, and a laundry list of repairs stared back at us. The potential, however, was undeniable. Multiple structures, walkability to town, and an unbeatable location next to our favorite national park in the world made this property stand out in a way that nothing else had.

This is the story of how we found, bought, and are now renovating a fixer-upper near Yellowstone National Park, including what we saw in these cabins, why we took the leap, and the adventure that’s only just beginning!

How We Got Here: From Travelers to Hosts

Our journey to buying a fixer-upper near Yellowstone started long before we ever considered owning a rental property. For years, we were simply travelers who hit the road for weeks or months at a time, shaping our version of digital nomad life.

Early in our twenties, travel wasn’t a huge priority for us. We canceled numerous trips due to work commitments, cross-country moves, and life changes. By 2019, that had started to feel like something we wanted to change, so when Jonathan was offered a fully remote role after I’d been working remotely for years, we took advantage of our location flexibility. We could work from anywhere with an internet connection and hit the road.

We started small with a one-week road trip to Virginia Beach to visit friends, then took a two-week road trip through North Carolina, splitting our time between Asheville and Raleigh. We traveled exclusively through short-term rentals because (1) our dog, Lincoln, joined our trips and (2) we needed more space to work and live from the road. (In 2019, pet-friendly hotels were rare, and short-term rentals were just generally more pet-friendly, affordable, and comfortable than hotels for longer stays.)

After those first few trips, we were hooked. Traveling while working remotely was freeing; we finally had the flexibility to explore new places without sacrificing our careers.

We wanted to keep traveling, so in early 2020, we hit the road full-time. We mapped out a year of travel, planning trips to destinations such as San Diego, Lake Louise, and Europe. We all know how 2020 actually played out, and we found ourselves shifting our plans to road trips across the United States instead. We gravitated toward quieter places like mountain cabins, small towns, and nature-focused destinations such as national and state parks.

From there, road life became our normal. We spent 2021 on a three-and-a-half-month road trip through Colorado and Utah. In 2022, we took a five-month road trip through New England. And in 2023, we split our travels between a three-week Alaskan adventure and a two-and-a-half-month road trip through the Rockies.

Along the way, we became experts in short-term rentals, not as hosts but as guests. We had stayed in dozens of Airbnbs and VRBOs and knew exactly what we liked in a rental, what made a place feel welcoming, and what details or amenities elevated a stay.

The Idea of Owning a Vacation Rental

As flexible travelers who stayed in places anywhere from one night to one month or more at a time, we had a unique perspective as guests. We worked remotely, so we valued good Wi-Fi and a functional workspace. We traveled with a dog, so we had firsthand experience with the limitations of pet-friendly stays. We’d seen everything from luxurious mountain cabins to rustic apartments and tiny homes and had developed a strong sense of what we loved in a stay and what could be improved.

From there, a natural thought occurred: What if we tried hosting?

It wasn’t just about running an Airbnb. It was about creating the kind of experience we had come to appreciate. The best short-term rentals weren’t just places to sleep; they added to our travel experiences, helping us connect with a destination in a meaningful way.

At the same time, we were also thinking about a second home base for ourselves. While we loved traveling to new areas, we also yearned for more tradition and stability, a place we could return to again and again.

The question was, where?

A Rental for Road Trippers

If we were going to invest in a vacation rental, it had to be in a place that aligned with how we traveled. We weren’t interested in a big-city rental or a traditional beach house. We wanted something that fit into the kind of trips we loved, something for road-trippers and outdoor adventurers.

Initially, we imagined buying land and building from the ground up. We wanted a property with multiple rentable spaces, such as a few small cabins, so we could host multiple guests at once and have a place for ourselves, too. It needed to be in an area with a lot to offer: national parks, scenic drives, hiking trails, and enough attractions to make it a year-round destination.

We started looking in places that fit that vision:

Colorado: An outdoor playground with Rocky Mountain National Park, ski towns, and endless recreation. We looked at Winter Park and Durango as potential locations.
New Mexico: We loved our time in Angel Fire, one of our stops during a 5-week New Mexico Road Trip in 2020, and explored the idea of setting up near the mountains.
Utah: Kanab was a standout option, with easy access to Zion, Bryce Canyon, and the Grand Canyon. Kanab is a roadtripper’s paradise!

We spent many months casually searching, watching listings in these areas we loved, and tossing around various ideas. But nothing quite felt right. Some properties didn’t have the zoning flexibility we needed. Others were too remote, too expensive, or didn’t offer the balance of activity we were looking for.

Our Short-Term Rental Checklist

Our goal was to create a stay that encouraged road trips, adventure, and immersive exploration of a destination. We wanted something that fit the Road Trip Local travel style, where guests could experience a region by car, taking in multiple attractions and outdoor experiences along the way.

With that in mind, here was our checklist:

✅ A Destination Near Multiple Attractions – We wanted a place where guests could road trip to multiple highlights. That’s why we considered places like Winter Park, Colorado, where visitors could explore Rocky Mountain National Park, Vail, and Denver. Or Kanab, Utah, which sits between Zion, Bryce Canyon, and the Grand Canyon.

✅ An Active, Outdoorsy Location – We wanted a destination that offered a variety of adventures and activities for people who enjoyed hiking, skiing, snowshoeing, rafting, scenic driving, or wildlife watching. That’s why we looked near national parks, mountain towns, and recreation areas rather than large cities.

✅ Multiple Rental Spaces – Whether it was a main house with a guest cabin or a small cluster of tiny homes, we wanted the option to host multiple guests at once. This wasn’t just about maximizing rental income; it was about having a place that felt like a second home for us when we wanted to visit.

✅ Walkability to Restaurants, Coffee Shops, and Breweries – While we didn’t want to be in a major city, we also didn’t want to be completely remote. We knew from experience that having a few restaurants or a small downtown within walking distance makes a big difference!

✅ Access to a Grocery Store Within 10-15 Minutes – This is another thing that makes a huge difference for us as guests. Easy and convenient access to a market was a must.

✅ A Year-Round Destination – Some places have a multi-month peak season and then sit empty the rest of the year. We wanted a location that had at least two distinct seasons, whether that was skiing in the winter and hiking in the summer or a mix of wildlife watching, road trips, and outdoor adventure.

✅ Pet-Friendly Potential – Since we had traveled extensively with a dog, we knew firsthand how difficult it could be to find great pet-friendly stays. We wanted a place where we could offer pet-friendly accommodations while maintaining high-standards of cleanliness for all guests.

✅ No HOA or Strict Rental Regulations – Some of the places we looked at had restrictions that made short-term rentals difficult, whether it was HOA rules or zoning laws. We needed flexibility, both for renting out multiple units and for developing the property to fit our vision.

✅ A Place We Love Spending Time In – Ultimately, this wasn’t just an investment property. We wanted a place we’d actually want to visit over and over again, as we hoped this would become a second home base for our own road trips and a place we could see ourselves enjoying for years to come.

With this checklist in mind, we kept searching, waiting for the right property to come along and, as we’d soon find out, sometimes the right place finds you!

Year of Yellowstone: The Year We Visited in All Four Seasons

Yellowstone has been one of our favorite national parks ever since we first visited during a 10-day Pacific Northwest Roadtrip in 2015. When we planned our 2023 travels and found ourselves Roadtripping the Rockies, we made Yellowstone one of our themes and decided to visit all four seasons within one calendar year!

Winter (February): We split our week-long trip between West Yellowstone, MT, and Gardiner, MT, spending our days searching for wolves in Lamar Valley, snowshoeing Yellowstone’s Northern Ridge, and snowmobiling the Grand Canyon of the Yellowstone. The quiet, frozen beauty of Yellowstone in winter was unlike anything we’d seen before.
Spring (May): Spring is the best time of year to see bears and baby animals in Yellowstone, so we came back to Yellowstone’s Northern Range in May. Sure enough, bison calves dotted the valleys, wolf pups were emerging from their dens, and bears with cubs were active near Tower-Roosevelt. It was a fun, playful time to be in the park.
Summer (July): On our way from Dallas to Jasper National Park, we stopped for a few days in Grand Teton National Park and Yellowstone. We hiked, watched the bison rut in full swing, and experienced the park at its busiest but also its most colorful.
Fall (September & October): We ended our Year of Yellowstone with a three-week trip during the peak of the elk rut. But this time, we weren’t just exploring for ourselves. Friends and family joined us, and we found ourselves playing the role of tour guides, helping them experience Yellowstone the way we had come to love it.

Yellowstone Tour Guides in Training

With friends and family in town, we planned our days around wildlife watching, knowing where to be at sunrise and sunset for the best chances to see wolves, bears, and bison. We mapped out efficient driving routes, keeping in mind the vast distances between major attractions. We gave tips on where to stand for the best views of geysers, when to expect traffic jams caused by bison herds, and which trails were worth the hike.

As we guided friends and family through the park, we realized just how much we had learned over the course of the year. We knew which pullouts had the best views, where to find restrooms in remote areas, and how to avoid the crowds without missing anything essential. (Eventually, we’d pull all of that knowledge and passion into an All-Seasons Yellowstone Travel Guide, hoping to help other Yellowstone visitors plan trips they’d never forget.)

For the first time, Yellowstone wasn’t just our adventure. It was something we were sharing. Watching family members light up at the sight of a bugling elk in the crisp fall air, seeing our friends in awe at their first glimpse of the Grand Prismatic Spring, or hearing the excitement as someone spotted their first bison or bear… it was rewarding in a way we hadn’t expected.

Unknowingly, this was laying the foundation for something bigger. Because only a couple of days later, we would stumble upon a listing that would make Yellowstone not just a place we visit but a place we could call home.

An “Extra Cute Bungalow” in Gardiner

It was the end of our three-week fall trip, marking the end of our Year in Yellowstone. As such, we weren’t planning to return to this area of the country anytime soon. We were about to check out of our hotel in Gardiner when Jonathan casually pulled up Zillow, something he’d done countless times over the past few years. It was more of a habit than anything at this point.

“Hey, Kel, there’s a house for sale literally a block away from where we’re staying right now,” he said. “Should we take a look?” When I glanced over his shoulder to see the listing, it wasn’t exactly impressive.

The cover photo was an exterior shot of the house, and from that alone, you could tell there was a lot of work needed. The siding was incomplete, and there were clear signs of unpolished construction work with exposed wiring, missing soffit, and general rough edges.

He flipped through the rest of the listing photos. The kitchen was old and outdated, with worn-out cabinets and countertops. One of the bathrooms had seemingly been built as an addition and was clearly unfinished, with exposed drywall, no baseboards, and missing trim.

From the description, it sounded like the property had multiple structures, which was the feature we were most intrigued by. It mentioned a dry cabin, a shed, and possibly an unfinished two-story apartment.

This was the selling point for us, or at least the thing that kept us flipping through the photos. The majority of the properties we’d considered in the past either didn’t have multiple structures or were too expensive if they did. Here was a property claiming four separate buildings—a main house, a dry cabin, a historic shed, and an unfinished apartment—at a price that was far below anything else we had seen with similar potential.

Still, we were apprehensive. The pictures gave the impression of one of those places someone is trying to make look nicer with bright lighting and wide-angle shots, yet it still screams ‘I need work’ …which isn’t exactly reassuring.

And yet, there was something about this place that made us hesitate before ruling it out completely. Since we were leaving town shortly, we knew if we were going to see it, it had to be now. So, Jonathan called the listing agent and asked if there was any chance we could take a look.

The listing agent was out of town, and so were the sellers. But to our surprise, she said yes… “You seem like nice people, so here’s the code.” (Truly.)

Just like that, we were about to solo tour a house we had only stumbled upon minutes before, in a town we weren’t even considering, with hours to spare before leaving with no plans to return. We drove one street over, parked in the driveway, and prepared ourselves for whatever we were about to walk into.

Keep Reading: (#2) Cabin Chronicles: First Impressions—A Lot to Love, A Lot to Fix