Your Property,
Peak Performance.
Trailhead provides end-to-end short-term rental management for owners across Southern Vermont. We handle the logistics; you collect the revenue.
Pristine Standards
Our dedicated cleaning and maintenance teams ensure your property is guest-ready 365 days a year.
Dynamic Pricing
We use real-time market data to adjust rates daily, maximizing occupancy through peak ski and foliage seasons.
Local Expertise
Based in the heart of Southern Vermont. We know every trail in Stratton and every back road in Manchester.
We handle the midnight calls so you don't have to.
24/7 Guest Support
From booking inquiries to keyless entry assistance, we are always on call for your guests — day, night, and every snowstorm in between.
Proactive Maintenance
Regular inspections and immediate repairs by licensed local contractors keep your asset protected through every Vermont season.
Omni-Channel Marketing
Premium placement on Airbnb, VRBO, and our own direct booking platform — with professional photography and copy that converts.
Compliance & Tax
We handle town registrations, lodging taxes, and safety compliance across every Southern Vermont jurisdiction we serve.
Rooted in Southern Vermont.
We focus exclusively on the towns we know and love. Staying local means we can be on-site within 30 minutes for guest needs, emergencies, or a fresh cord of firewood.
Portfolio-wide guest rating across Airbnb and VRBO.
Response time to any guest or owner request.
We strive for five-star reviews like this
“Thank you for the stay! Home was very clean and the area is beautiful! Host is very responsive and answered any questions promptly. Short drive to Mt. Snow which is a great area for skiing and family activities. Would stay again!”
Curious what your home could earn?
Tell us a little about your property. We'll send back a custom revenue forecast within one business day — no obligation.