In the aughts, Annedria and Andrew Beckham bought a little white house in Sherwood surrounded by grapevines and evergreens, where they founded Beckham Estate. After moving farther north, they turned the house into a vacation rental: three bedrooms, two woodburning fireplaces, an outdoor grill, and unparalleled access to the vineyard and on-site tasting room. “Agriturismo,” Andrew says. “Every time I go to Europe, I don’t understand why we don’t have more of that here.”

Immersive lodging usually means ski-in chalets, treehouse resorts, beachside bungalows. Staying on the vineyard isn’t as immediate of a thought. Though it absolutely should be. At Abbey Road Farm in Carlton, for instance, three transformed grain silos make a five-room bed-and-breakfast, where chef Will Preisch serves a five-course morning meal pulled from 82 acres of farmland visible from some rooms. The winery tasting room is a picturesque walk away, as are the farm’s donkeys, goats, and 15 varieties of wine grapes.

At the Black Walnut Inn & Vineyard, valley view suites open onto private balconies that show off the Dundee Hills, while The Setting Inn—a relative of a Napa winery and hotel—situates its guest rooms to stare out at the Chehalem Mountains. David Cox, its general manager, says most guests schedule a private tasting, a nice final flight after a day touring wine country. However, you might instead take an evening walk with an open bottle of estate pinot, meandering the vines it was made from, Cox says, “picnic style.”

For deeper immersion, look to the barely touched vineyard cottages and cabins scattered across the valley’s several American viticulture areas. Stoller and sibling winery Chehalem have multiple spacious rentals well-suited to group trips that just happen to be walking distance from a tasting room. More intimate is the single cedar cabin perched above Beacon Hill Winery & Vineyard, depicted on the estate’s wine label. It’s rustic. You’ll have to walk outside to access the detached bathroom. But where else can you drink pinot on a private wraparound deck looming over the 20-year-old vines that grew the grapes in your glass?