The Hostaway Experiment:
The Hostaway Experiment: When Automation Becomes Liability
Title: The Hostaway Experiment: When Automation Becomes Liability
I signed up for Hostaway because I wanted to depend on Airbnb less.
I could see where their corporate model was heading. You only have to look at what happened to Vrbo after it married Expedia to understand what was coming next. Once Vrbo went corporate, hosts became data points and travelers became transactions. Airbnb was starting to show the same signs. Bigger profits, less transparency, fewer protections for small local hosts who actually maintain their homes and communities.
I did not want to get caught in that shift. I wanted to build my own direct booking business. I wanted to communicate directly with guests, set fair policies, and manage relationships without a corporate algorithm.
That is why I signed up for Hostaway. It promised freedom, automation, and control. Instead it gave me international billing chaos, broken promises, and enough liability that I had to add screening and insurance tools.
Why a channel manager at all
I manage multiple properties in Greensboro NC. Short term, mid term, and traditional rentals. Syncing calendars across platforms is like juggling knives uphill. For the short term rentals, a channel manager seemed logical.
What Hostaway promised
Calendar sync for Airbnb, Vrbo, and Booking.com
QuickBooks integration included in the subscription and described as robust
ACH payments coming soon
Messaging and guest management automation
The base subscription was over 300 dollars per month for eight listings. Then there was a per listing dynamic pricing fee, per booking fees, international fees on every Stripe payment, and a separate payment processor I had to bring. It was supposed to make the business easier. It made it more complex and more expensive.
The hidden costs of automation
Hostaway bills from Finland. My bank flagged every monthly charge as fraud. After months of back and forth, Hostaway sent threatening emails that they would suspend my account if I did not pay immediately.
I opened a business credit card only to pay Hostaway because TowneBank would not allow those recurring international charges. Between subscription, add ons, transaction fees, and time, the real cost was closer to 6,000 dollars for the year.
The customer support that was not
Every message created a new ticket number. New number, new person, no continuity. Some tickets included a link to a training video. The video did not match my screen.
I use Apple devices. Maybe that was part of it, but the videos were so off they were unrecognizable as help. It felt like getting a car manual when I asked for jumper cables.
One bright spot. I was assigned a dedicated support person, Tyra. Without her I would not have made it through onboarding.
Liability they do not warn you about
Direct bookings shift risk to the host. To protect guests and my business I added:
Truvi for guest screening plus guest paid damage and liability coverage. There is a monthly fee and a per booking fee. Guests also pay about 40 dollars for coverage. Human run and helpful.
Special rental insurance with David Wilkins at Allen Tate. Excellent guidance and dialed coverage.
Even with safeguards, the risk was obvious. The platform is no longer the intermediary. You are.
Disconnecting is not a switch
Leaving Hostaway took weeks. Multiple online appointments. Manually unsyncing calendars. Rebuilding messages and systems for Airbnb, Vrbo, and Booking.com. Tyra spent hours untangling this with me. I stayed a full year because I planned the learning curve and because she helped.
Continue to Part 2: The Fink Effect (link this to Post 2 once it is published)
