In March, Isabelle Chicoine and Karim Houry spent $1.2 million on a circa-1830s bed-and-breakfast in Woodstock, Vt., that’s so quaint it could have been painted by Grandma Moses. But to make it their home, they needed a business plan, a marketing strategy and internet savvy.

“Developing the website, doing the marketing takes a lot of our time,” said Ms. Chicoine, 52, who had been working as director of communications for a private school in metro New York before she decided to ditch it all for a life of changing sheets, scrambling...