It's a little after 11pm on a Friday night in July. Tanglewood has just let out, and a guest is pulling back up to one of our homes, ready to call it a night. They walk up to the door, go to let themselves in — and the keypad won't cooperate. It's past our normal hours. There's nobody sitting in an office. And that guest doesn't need an answer in the morning. They need one right now. That moment, right there, is guest communication when it counts most.

Here's the thing about a moment like that. Yes, how quickly you reply to a guest plays a real part in how your listing shows up in the Airbnb search algorithm — fast, reliable communication gets rewarded. But honestly, that's the smaller reason I care about it. The bigger one is simple: leaving a guest stranded at the door when they've got a problem just isn't how we run this business. It's not good hosting. Being there for your guests, especially when something goes sideways, is the whole job — and it's the part that's hardest to keep up 24 hours a day. That's the pain point I dug into last time. Today I want to show you what we're doing about it.

Enter HostBuddy AI

About a month ago, I went to an AI summit built around the short-term rental industry, and the team from HostBuddy AI gave a great presentation on their new product. I left genuinely excited. In plain terms, HostBuddy lets us answer guest questions fast during our after-hours window — roughly 9 p.m. to 9 a.m. — while still pulling a real person (me) in the moment it doesn't have the right answer.

What makes it click is that it's pulled all of our property information straight from our management system, Hostaway, so it already knows the answers to most of what guests ask. Where's the backup key when someone's locked out at midnight? How do you get to the washer and dryer that's tucked behind a locked owner's closet? Are those dates in August still open? Can we do a little discount on a longer stay? HostBuddy can field a lot of that on the spot, in a warm, helpful voice, without anyone on our team having to be awake for it.

Teaching It, One Home at a Time

Now, this isn't software you just switch on. We're running it after hours right now, on purpose, while we teach it. When a guest asks something HostBuddy doesn't have an answer for yet, we go into the system and build that answer in — so the next time a guest asks, it's ready and waiting.

That means it's genuinely learning our homes, question by question. Can we rent kayaks? Can we bring our own boat and dock it at the home's private dock? Little by little, it's turning into a deep, home-specific brain for every property we manage. It's pretty cool to watch it take shape.

Why This Is How We Run BVR

As we keep building this business, I'm convinced that continually improving our tech stack is what lets us manage homes properly at scale — and tools like HostBuddy are a big part of that. It gives our team their time back. Instead of typing the same answers around the clock, we get to focus on the things that actually move the needle, like reaching out to past guests to book their next stay with us directly.

And it does more than answer questions. It quietly organizes everything that comes up — a maintenance issue gets logged, and when a guest mentions they're celebrating something, that gets captured too. So if a family is coming up for a birthday, we know before they arrive, and we can leave flowers or balloons waiting at the house. It's becoming almost a little CRM for our guests, which means we get to spend our time on the personal touches that make a Berkshire stay memorable.

Tools like HostBuddy AI are a big part of how we're taking BVR to the next level, and I couldn't be more excited about where this is headed. If you own a home in the Berkshires and you're curious what it would feel like to hand off the 2 a.m. messages — and everything else — to a team that hosts like this, reach out. We'd love to talk.

Happy hosting,
Jaryn
Berkshire Vacation Rental Co.