Every property was booked solid heading into the holiday weekend — exactly what you want to see in early July. Then a massive storm rolled through the county in the middle of the night on the 3rd. I woke up around 6 AM on the 4th to find the power out at our own house, and figured pretty quickly that if we were out, a lot of the properties probably were too. Sure enough, the guest messages started coming in.

The good news was that the outages were county-wide, not property-specific, which meant nothing was broken at any of the homes. So our focus went straight to communication: reaching guests quickly, empathizing with a genuinely uncomfortable situation — no AC on some of the hottest days we've seen all summer — and giving everyone a realistic timeline for when power would come back. The utility crews were fantastic, and nearly every property was back up and running by noon on the 4th.

We're still waiting on some reviews to come in from last week's guests, but the early read is that people still had a great holiday in the Berkshires — power outage and all.

We've Got a New Business Line

We've set up a dedicated business line for Berkshire Vacation Rental Co. The new number is (413) 429-9558.

We'll be using this line for most day-to-day communication — new business and guest messaging — but here's the part worth noting: for after-hours situations, especially emergencies like a power outage, this is the best way to reach us. It rings 24/7, so you'll always be able to get through.

Go ahead and save this number to my contact, or add it alongside the one you already have. You don't need to delete my original number — keep it so you've always got a direct line to me if you need it.

Something New We're Testing: AI Messaging

A couple weeks back, I attended an AI summit built specifically for the short-term rental industry. The workshop I was most interested in came from a company called HostBuddy — an AI messaging tool made for hosts like us. We've already built out the back end and have started quietly testing it internally.

The appeal is pretty simple: it gives guests 24/7 communication, and it acts as a backup so I can occasionally get out for a bike ride without worrying I'll miss a guest message. And it's genuinely impressive — it troubleshoots guest questions well, and the tone of the communication is surprisingly natural.

That said, it still needs real work before we're happy with it. We're a long way from letting it talk to actual guests unsupervised — for now it's an internal test, with a real person (me) still in the loop on everything. Just something cool we're working on, and I wanted to keep you in the loop.

Want to learn more about HostBuddy? [Click here ]

That's the update for this month. As always, reach out anytime — you know where to find me (and now you've got a second number for it).

 - Jaryn

P.S. — The weather up here has been absolutely beautiful lately. Our calendars are pretty full this summer, but there are still a few open slots if you want to slip in an owner's stay. Come visit us in the Berkshires — we'd love to host you.