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What's Driving Bookings in The Berkshires Right Now

What's Booking in The Berkshires Right Now

A few notes from the field on what guests are actually asking for this season.

I talk to guests every day. Inquiries, check-in messages, the occasional 11pm "where's the extra blanket" text. Over time you hear the same things over and over — and what guests ask for is one of the better leading indicators we have for what's going to book.

Lakefront with kayaks.

The first warm weekend hits and the inquiries flip overnight. Everyone wants to be on the water — not near it, on it. Walk out the back door, drag a kayak to the dock, on the lake in five minutes. Our lakefront homes with kayaks on-site book faster, command higher rates, and pull stronger reviews. If you own near water and you don't have kayaks, that's the easiest upgrade you'll make this year.

Pet-friendly.

Most owners default to no pets. I get it — the risk feels real. But demand for pet-friendly homes in the Berkshires keeps growing, and supply hasn't kept up. That gap is where the booking premium lives.

EV chargers.

This one's growing fast. More inquiries every month asking whether we have a Level 2 charger. Most Berkshires listings still don't have one. Owners who install now are getting an edge that's only going to grow.

Hair dryers.

This one cracks me up. I pulled data from our pricing software on this one and couldn't believe how many people filter for hair dryers. The number of guest messages I get about hair dryers is genuinely surprising.

The lesson here isn't really about hair dryers, it's that the unsexy stuff matters. Good towels. Blackout curtains. Enough hangers. The properties that nail the small stuff are the ones with the best reviews — and the best reviews book.

Quick Take

Demand is there. Bookings are pacing well into summer. The question for owners isn't whether the market is healthy. The question is whether your home is set up to capture it. The four above are a good place to start.

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