Turn Your Property Into a Profitable Vacation Rental -Without Losing Your Sanity.

A no-fluff guide to help as The Vacation Rental Host Playbook is your no-fluff blueprint for building a profitable short-term rental business—without needing a huge property, prior experience, or burnout energy.

The Vacation Rental Host Playbook

is your no-fluff blueprint for building a profitable short-term rental business—without needing a huge property, prior experience, or burnout energy.


It’s for people who want freedom, flexibility, and the kind of work that fits around their life—not the other way around.

Inside, you’ll learn exactly how to:


Launch and manage a vacation rental (even if you’re starting small)

Avoid the newbie mistakes that tank bookings and eat profits.

Create a guest experience people rave about—and return for.

Step into a lifestyle of seasonal income, location-flexibility, and actual adventure.

This isn’t a “course” to collect dust.

It’s a plug-and-play system for people who want to

host smarter, earn sooner, and live freer.

With decades of hands-on experience as a profitable vacation rental host, I’ve seen everything from last-minute cancellations to full-on plumbing disasters—and built systems to handle it all.

I created this course to save you the stress, the guesswork,

and the “I wish I’d known that” moments.

You’ll walk away knowing exactly what to expect—and how to turn your short-term rental into a long-term win.


Season by season, we build with intention—not guesswork.

Get the tools, the support, and the clarity to do it right.

Every design detail, guest experience, and system at The Chicory House is something we teach inside our programs.

Want to test-drive the lifestyle before you build it?

This is where you start.

The Chicory House: Where Hosts Go to Learn by Living It

“Not just a place to stay—our B&B is a live classroom for aspiring hosts.”

Nestled in Paradise Valley, Montana—just 38 miles from Yellowstone—our B&B is more than a cozy getaway. It’s living proof that hosting can be intentional, profitable, and soul-filling.

Soak in local hot springs, hike wildflower trails, and experience the exact systems we teach inside the Playbook and Course—live and in-person.

Whether you're here for adventure or to quietly observe what a five-star guest experience really looks like, this isn’t just a vacation—it’s inspiration with strategy baked in.

Are you part of the T.H.O.R. industry, or do you want to be?

T.H.O.R. (Tourism, Hospitality, and Outdoor Recreation)

—and it's the heartbeat of seasonal work.


You’re the guides, the camp cooks, the lodge hosts, the outfitters, and the adventurers. You help others experience the wild, the restful, and the unforgettable. You trade time clocks for trailheads, and office desks for open skies.


If your work revolves around travel, nature, people, and place—you’re in the right spot.

And this course was built just for you.

Empowering Entrepreneurs in Seasonal Lifestyles is your roadmap to building income, freedom, and purpose doing what you already love.

Whether you're in between seasons or ready to make your next move, I’ll help you turn your experience into a sustainable, self-employed lifestyle.

Curious About Becoming A Vacation Rental Host?

Curious About Becoming A Vacation Rental Host?

Thinking about starting a short-term vacation rental business but want real, hands-on experience before diving in? This blog introduces our unique “Stay & Learn” mini vacation at The Chicory House B&B... ...more

Short Term Vacation Rental Help

June 12, 20256 min read

The Ultimate Guide to Setting Up Your Airbnb – Before You Begin or Buy

The Ultimate Guide to Setting Up Your Airbnb – Before You Begin or Buy

Dreaming of hosting on Airbnb and earning extra income? Before you dive in, learn the key steps to set up a successful short-term rental from start. From choosing the right property to pricing, furnis... ...more

Short Term Vacation Rental Help

March 01, 20255 min read

Summer Season is Here ~ And So Are the Wildflowers, Gardens, and Guests at The Chicory House 

Summer season is here, and The Chicory House is buzzing with blooming wildflowers, fresh garden beds, and guests from all over the world. This post shares a behind-the-scenes look at how we’re celebra... ...more

Short Term Vacation Rental Help

June 12, 20255 min read

Summer Season is Here ~ And So Are the Wildflowers, Gardens, and Guests at The Chicory House 

Curious About Becoming A Vacation Rental Host?

Thinking about starting a short-term vacation rental business but want real, hands-on experience before diving in? This blog introduces our unique “Stay & Learn” mini vacation at The Chicory House B&B... ...more

Short Term Vacation Rental Help

June 12, 20256 min read

Curious About Becoming A Vacation Rental Host?

Our 2025 Season is up and open!

Let's go!! We have the fire. the food and the cast iron. Now all we need is YOU!! ...more

Everything Cast Iron

June 03, 20252 min read

Our 2025 Season is up and open!

testimonial

Jakub

"This was probably the best well-thought out airbnb we’ve ever been to, everything was set up to make you comfortable and the place was really clean. Great location and beautiful surroundings."

Georgia

Sheila had everything and more for us. She couldn’t have been more hospitable and understanding of our late check in time. I’d recommend without hesitation. She also helped tremendously with Yellowstone recs. if there was a shortlist for the best airbnb host Sheila would surely win it.

Natesan

Probably the best Airbnb I've ever stayed in! Sheila ensures that the guests have the best possible experience and that the house and room are extremely well maintained. Would definitely recommend this location to folks who are visiting Yellowstone.

Frequently Asked Questions

“Everything you need to know before you host, scale, or stay your way into a seasonal lifestyle.”

“What makes your Playbook different from other vacation rental guides?”

Most guides are written by marketers. This Playbook was built by a real host, running a real B&B, in one of the busiest seasonal markets in the U.S. Every tool inside is something I’ve tested, tweaked, and still use today to run my own five-star property. This isn’t theory. It’s what works.

“I don’t have a property yet—should I still get the Playbook?”

Yes. The Playbook was designed to help you think and act like a host before you own. From identifying a viable property to avoiding rookie mistakes during setup, it gives you a launch plan with fewer headaches and more bookings from Day 1.

“What’s the difference between the Playbook and the Empowering Entrepreneurs Course?”

The Playbook helps you launch. The Course helps you scale. The Playbook is a step-by-step system to get your first property up and running. The Course dives deeper into business strategy, boundaries, seasonal planning, and turning hosting into a sustainable lifestyle—not just a hustle.

“How do I know your strategies work?”

You can stay inside the strategy. The Chicory House, my own B&B, runs on the exact methods I teach. From guest experience to pricing, what you’ll learn in my programs is visible in every stay. It’s not just proof—it’s a live demonstration.

“Is this course only for Airbnb hosts?”

No. The tools apply across vacation rental platforms—or even your own direct booking site. Whether you’re using Airbnb, VRBO, or building a unique experience like my B&B, the core systems work across all of them.

“Do I need experience in business or hospitality to succeed with this?”

Absolutely not. I built my hosting business with no degree, no funding, and no formal hospitality background—just grit, systems, and seasonal experience. If you’re coachable and ready to work smart, this is built for you.

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