We own and operate this thing called “Little Owl Cabin.”

It started around 2006, in New York City of all places. Val was an affordable housing developer in the South Bronx; Ryan was a public policy consultant, designing and managing resource conservation programs.

We used to take lots of trips to ski mountains and National Parks, back when VRBO was Almighty and Airbnb was a scrappy startup. As often as possible, we stayed in vacation rentals. We were spending too much time in boring hotels on business travel, so real homes were the perfect antidote to those soulless boxes whose charms were usually limited to cable tv and loyalty points.

Invariably, we left those vacation homes with a long list of of things we wanted to change. The kitchens were always terrible places to cook. Bedding quality was inconsistent. The decor and furnishings were usually kinda dated and chintzy, and lighting quality was an afterthought. We didn’t like having to contact the owner when things didn’t work, or when basic systems and appliances were too complicated to understand and operate.

With Vermont in our sights, we were certain we could deliver a better experience. But, we were spending way too much time in the office, and never finding the time to do a diligent real estate search, let alone design our ideal vacation rental.

In 2013, Ryan received a job offer in Seattle that promised fewer hours and less travel. Deal! We loved our new geography and all the recreational opportunities it promised, but after two years at that new job, the itch to do something completely different was too strong to ignore. The clock was ticking, and middle age was looming. If there was gonna be a second act, it was now or never.

Ryan ditched that job and resolved to learn something completely new: lots of courses, tons of networking, endless rejections…and a home renovation project in Packwood.

We bought our first cabin in the Summer of 2015. It was in rough shape, but the fundamentals were solid: it backed up to national forest and a creek; it was surrounded by mature trees, and the price was right. We made an offer on the spot, and closed several weeks later. Between coursework and networking events, Ryan binged YouTube carpentry tutorials, bought some tools, and started hacking away at our new cabin—never imagining that hosting could possibly become a full-time career.

Eventually, the rejections were declining, and Ryan was getting second and third interviews for tech(ish) jobs. At the same time, our booking traffic was ramping up, and within a few months, this hosting business had wildly exceeded our estimates. So much so that we got creative and bought a second cabin in 2016.

Between building a new business from scratch in the mountains or logging more office time, the decision to go all in on hosting was a no-brainer. By 2020, Val left the affordable housing world; we moved to Packwood, and in 2022, we finished construction on our fourth and fifth cabins!

Little Owl is every bit a passion project. We love creating spaces that help people transcend the ordinary, and discover joy and adventure in this breathtaking corner of the world. Our cabins are expressions of our loftiest desires as travelers: truly unique, thoughtful, visually stunning spaces that prioritize comfort, calm, curiosity and elevated design, with minimal planning and fuss. If we’re doing it right, you should arrive to a space that’s beautiful, amusing and inspiring, where everything just works as you expect.

Curious about our journey? Subscribe to our emails to hear more of the story!