Manor Hill Tavern set to open next month in Ellicott City

William D. Burns

Airbnb's homestay network flourishing in the Berkshires

Adam Sugarman owns a two-bedroom apartment in Pittsfield but had difficulty finding regular tenants to occupy it.

So in the winter of 2015, Sugarman decided to take a "calculated risk."

"I threw together some furnishings and put it up on Airbnb," said Sugarman, who lives in Great Barrington. "I had some familiarity with short-term rentals. My brother and his wife were doing it in Miami. So I put it out there and it took off."

The result?

"I lucked out," he said. "I was booked for the whole spring."

Sugarman isn't the only county resident who has benefited from Airbnb, a peer-to-peer online marketplace and...