The American getaway experience is one of extremes. There’s a glut of over-the-top rural retreats—Blackberry Farm, in Tennessee; the Point on Saranac Lake, in upstate New York; the Resort at Paws Up, on a 37,000-acre cattle ranch in Montana—where the price of a week-long stay could easily rival that of a gently used Jeep Wrangler. And then there are the thousands of charmless, featureless roadside motels that have little in common with the smartly conceived, 50s-era stopping points such as Howard Johnson, which initially begot them.

A view of the bedroom and galley in a Cape Cod Airstream.

The joy of an old-school, lo-fi getaway is maddeningly elusive, which explains why so many urbanites have taken up glamping. But AutoCamp has an even better solution. By investing in beautiful stretches of land and hundreds of vintage Airstream trailers—and then using clever design to integrate the two—the San Francisco–based company has pioneered a new type of indoor-outdoor hotel.