Curious About Becoming A Vacation Rental Host?
Thinking About Getting into the Vacation Rental Business? Come “Stay & Learn” With Us Near Yellowstone!
If you've been dreaming of starting your own short-term vacation rental business, but you're not quite sure where to begin, why not take a mini vacation and learn the ropes at the same time?
Our “Stay & Learn” experience at The Chicory House B&B offers hands-on guidance, behind-the-scenes access, and real-world insight into what it takes to run a successful short-term vacation rental business—all while enjoying the stunning scenery of Paradise Valley, Montana, just 38 miles from Yellowstone National Park.
Whether you're still in the dreaming phase or already have a property in mind, this immersive experience is designed to give you clarity, confidence, and practical knowledge—all in a relaxed, welcoming environment.
Why a “Stay & Learn” Vacation Could Be Your Best Investment Yet
Starting a short-term vacation rental business can feel overwhelming. There are regulations to follow, platforms to navigate, guests to manage, and systems to set up. It’s easy to get stuck in research mode, unsure where to begin.
That’s where we come in.
At The Chicory House, we’ve hosted thousands of guests and weathered every season in the rental world—from booking booms to burnout. Our Stay & Learn mini vacation lets you experience the daily flow of a working vacation rental business, ask your burning questions, and learn the truth behind the Instagram filters.
We pull back the curtain and walk you through:
Guest communication and hospitality tips
Cleaning routines and check-in procedures
Pricing strategy and profit planning
Property setup, decor, and photography
Listing optimization for Airbnb and VRBO
Local laws, HOA rules, and safety best practices
This is real education for real hosts—with breakfast on the porch and the mountains as your classroom.
Who Should Book a “Stay & Learn” Experience?
This isn’t just for dreamers—it’s for doers.
If any of the following sounds like you, a Stay & Learn trip might be the perfect next step:
You're interested in starting your own short-term vacation rental business, but don’t know where to begin.
You’ve been watching YouTube videos and scrolling forums but want real-life insight from a working host.
You already have a property or plan to buy one soon and need guidance on setup and systems.
You’re tired of courses that don’t feel hands-on or grounded in real experience.
You want a break from your 9-5 but want to learn something meaningful while you unwind.
This isn’t a retreat—it’s a working, real-world crash course in hosting, with pancakes and mountain views included.
What You’ll Learn During Your Stay
During your time at The Chicory House, you’ll shadow a seasoned host (that’s me!) and get personal guidance in every area of the business. You’ll leave with a clear action plan, helpful templates, and the confidence to step into your own short-term vacation rental business.
Here’s What’s Included:
Daily breakfast and Q&A time
Live demos of check-in prep, guest communication, and cleaning checklists
Walkthroughs of our guest spaces, kitchen setup, storage systems, and behind-the-scenes routines
A 1:1 coaching session to map out your property and profit potential
A bonus guide to our favorite digital tools (like messaging automation, booking calendars, and review follow-ups)
Optional add-ons include:
A photoshoot coaching session to help you style and shoot your own rental
A cast iron dinner under the stars (yes, we teach cooking too!)
Evening wine on the porch where we talk marketing, money, and mindset
What Makes This Experience Unique?
What sets our Stay & Learn experience apart is that it’s built by a host, for future hosts.
I’ve spent over 30 years working in tourism, hospitality, and outdoor recreation—and I still live and breathe this life every day. From building bunkhouses to balancing bookings, I’ve learned (and re-learned) what works. This isn’t a theory class—it’s a hands-on, sleeves-rolled-up experience.
You’ll leave with:
✅ Clarity on whether the short-term vacation rental business is the right fit for you
✅ Real-time experience with guests, turnovers, and daily operations
✅ Templates, checklists, and resources you can take home and start using immediately
✅ Renewed confidence in your ability to create a lifestyle of freedom and purpose
What’s It Like to Stay at The Chicory House?
Imagine waking up to golden morning light streaming over the Absaroka Mountains. Fresh-baked biscuits, coffee on the porch, and the soft sound of horses in the pasture. That’s how your day begins.
The Chicory House B&B is nestled in Paradise Valley, Montana, just a short drive from Yellowstone’s north entrance. It’s rustic, welcoming, and filled with charm. From comfortable beds and crisp clean linens to a kitchen built for cast iron cooking, everything we do reflects our values: authenticity, comfort, and heart.
Our guests come for the views and stay for the stories—and now, you’ll get to learn the behind-the-scenes of what makes it all work.
What Guests Are Saying
“I stayed at The Chicory House to learn about vacation rentals and left with more than just a business plan—I left with a purpose. Sheila’s heart and knowledge shine through every part of the experience.”
— Miranda H., future host from Oregon
“The hands-on walkthrough of how to run a short-term vacation rental was game-changing. I saved months of research by just watching how it’s done in real life.”
— Jake T., small cabin host in ColoradoExternal Resources You Might Love
Airbnb Hosting Resource Center
Guests enjoying coffee and sunrise during a Stay & Learn session at The Chicory House B&B
Ready to Turn Curiosity Into Confidence?
Starting a short-term vacation rental business doesn’t have to be guesswork. With our Stay & Learn experience, you’ll get hands-on training, real answers, and the inspiration you need to build a business and a lifestyle you love.
👉 Book your Stay & Learn experience today at: bit.ly/TheChicoryHouse-nearYellowstone
📍 Or come visit us in person at The Chicory House B&B, nestled in beautiful Paradise Valley, Montana
📧 Questions? Email us directly at [email protected]
Something to think about~
This is more than a mini vacation—it’s a chance to reset your vision, realign your goals, and build something meaningful. Whether you're here to gather ideas, crunch numbers, or just soak it all in—we're ready to welcome you.
And who knows? That little spark you’ve been sitting on… it might just turn into your next big adventure.
Summary Checklist
✅ Real-life, immersive training on running a short-term vacation rental business
✅ Includes meals, coaching, and Q&A sessions
✅ Located near Yellowstone in Paradise Valley, Montana
✅ Hosted by a seasoned expert with 30+ years of experience
✅ Beautiful, relaxing environment to learn and recharge
Learn the ropes of hosting where the wild meets warm hospitality,
Sheila
#StayAndLearn #VacationRentalBusiness #YellowstoneGetaway #HostTrainingRetreat
