Local Vermonters. Passionate Hosts.
Simple Stay Property Management was born from a love of Vermont and a belief that short-term rental management could be done better — with more care, more attention to detail, and more genuine hospitality. We partner with homeowners across the Northeast Kingdom to thoughtfully list and manage their properties, combining five-plus years of experience with a deeply personal approach.
Our Journey
Became Airbnb Superhosts
Achieved Superhost status — and have maintained it every year since.
Top 1% of Airbnb Listings
Achieved top 1% of rental listings on Airbnb.
100+ Five-Star Reviews
Reached more than 100 five-star reviews across our properties.
Launched Simple Stay Property Management
Started helping other owners cohost and manage their homes in Vermont.
Top 5% of the Rental Market
Within 6 months of launching, achieved multiple properties listed in the top 5% of the rental market.
100% Occupancy
Achieved 100% occupancy across multiple properties for 3 consecutive months.
Expanded to 10+ Properties
Grew our managed portfolio to more than 10 properties.
1,000+ Guests Hosted
Hosted over 1,000 guests across our properties.
Superhost Since 2021
Maintained Superhost status annually since 2021.
Breezeway Certified Inspectors
Professionally certified to inspect and document short-term rental properties.
Maintaining 4.99+ Rating
Across our entire portfolio of properties.
Featured on Dirt & Glass
Our tiny house was featured by one of the most influential cabin photographers on social media.
Featured by Dirt & Glass
One of our properties — Simple Haven — was featured by Dirt and Glass, a nationally recognized cabin and outdoor lifestyle photographer with a highly engaged following. This recognition reflects the quality and character of the stays we curate.
"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 couldn't have been happier with our choice and would stay there again in a heartbeat."