Your Property. Our Expertise. Exceptional Results.
Simple Stay Property Management takes the complexity out of short-term rentals — so you can enjoy the income without the stress.
Get in Touch →Trusted & Certified
We've heard the stories.
Here's how we do things differently.
"I had no idea what I was actually paying for."
One transparent management fee. No hidden markups, no surprise line items. You see exactly what you earn.
"My manager disappeared when bookings slowed down."
We proactively communicate — performance updates, market insights, and honest conversations about what's working and what we're adjusting.
"I felt like property #347 in a spreadsheet."
We manage a focused portfolio in one region. Every property gets personal attention, not automated workflows.
"Guest complaints about cleanliness kept coming."
Breezeway-certified inspection before every stay. We document property condition and catch issues before guests do.
"My listing looked like every other rental."
We write listing copy and coordinate photography that captures what makes your property unique — not templates.
"They'd never even been to Vermont."
We live here. We know which local restaurants to recommend, which trails to suggest, and what guests in the Jay Peak region actually want.
"Maintenance issues piled up until something broke."
We flag and coordinate maintenance proactively. Small fixes now prevent expensive problems later.
"My rates never changed, even during peak season."
Dynamic pricing adjusted for seasonality, local events, and real-time market demand. Your rates work as hard as we do.
Ready to experience the difference?
Contact Us →The Simple Stay Difference
Hands-Off Management
We handle everything from guest inquiries to check-out inspections. You receive your earnings — not the headaches.
Superhost-Level Hospitality
As certified Airbnb Superhosts since 2021, we maintain the standards that earn 5-star reviews — consistently.
Local Knowledge, Personal Touch
We're Vermonters. We know Jay Peak, the region's hidden gems, and what guests are actually looking for.
Professional Property Inspections
As Breezeway Certified Short-Term Rental Inspectors (2026), we ensure your property is always guest-ready and professionally maintained.
Optimized Listing Performance
From photography guidance to pricing strategy, we maximize your occupancy and nightly rate.
Transparent Communication
You're always in the loop. Clear reporting, proactive updates, and a team that treats your property like their own.
Average Airbnb rating across our entire portfolio
What Our Guests Say
"This place is a real gem! A very cozy home with a breathtaking view... Annie is a wonderful host who is friendly, responsive, and quick to reply. We had a lovely weekend here and would absolutely love to come back."
"Such an incredibly well thought out use of space! The beautiful aesthetic and cozy amenities made for a super restorative stay. Annie was extraordinarily communicative, provided clear instructions, and offered great local recommendations."
"We couldn't have been happier with our choice and would stay there again in a heartbeat. We had one small issue and Annie was there to fix it within the hour of our reaching out — she is truly the best host!"
Ready to make your Vermont property work for you?
Let's talk. We'd love to learn about your property and share how Simple Stay can help you earn more while doing less.
Contact Us →