One of Oregon wine country’s best-kept secrets is the magic of cellar season each winter from January through March, when gnarled vines sleep beneath silvery mist and wine cellars hum with the promise of future vintages in neatly stacked barrels. It’s a serene time to explore vineyards, made even more inviting by a growing array of winery stays, from secluded vineyard cottages to refined countryside estates. Here’s where to savor a deeply calming getaway at the state’s coziest wine-country retreats.
Quiet Luxury and Wellness in the North Willamette Valley
High in the Dundee Hills — roughly 30 miles southeast of Portland — Foley Wines Dundee Hills looks out over cascading ribbons of pinot noir and chardonnay vines. The intimate nine-room villa embodies quiet luxury, while the neighboring Grange Estate channels elevated farmhouse style, with most rooms featuring fireplaces and deep soaking tubs. Just steps away, the 14-seat wine restaurant Anthology anchors the experience with a memorable 10-course tasting menu, spotlighting seasonal plates.
Just down the road in Dayton, the fifth-generation, family-run Durant Vineyards offers an equally enchanting stay. Guests can settle into Stoneycrest Cottage, a modern two-bedroom retreat surrounded by 40-year-old vines and steps from the estate olive grove that Durant uses for its famed olive oils.
In Carlton, wine country dreams meet farm life at Abbey Road Farm, an 82-acre estate where beautifully renovated grain silos have been transformed into stylish places to sleep. Mornings begin with leisurely strolls through vineyards followed by meet-and-greets with photogenic farm animals — mini donkeys, perky goats, heritage-breed pigs and a flock of chickens.
Closer to Beaverton, the Sosta House bed-and-breakfast is a wellness-forward retreat designed for slowing down. The experience unfolds from garden-inspired breakfasts to a private outdoor oasis with a barrel sauna and cold plunge overlooking vineyards and wetlands. The intimate property offers three minimalist guest rooms, each accented with artwork by the owner’s family and friends. Inside, the Great Room beckons with a toasty fireplace, a curated vinyl collection and a book-swap library.
Near McMinnville vineyard views unfurl toward the Oregon Coast Range at Youngberg Hill, a family-run winery and inn rooted in heartfelt hospitality. Guests linger on the hilltop veranda, unwind beside in-room fireplaces and wake to a gourmet breakfast. Guided tours and tastings are available, though wandering the vineyards solo might include encounters with shaggy highland cows and grazing sheep.
Vineyard Views in Central and South Willamette Valley
South of Salem, iconic Willamette Valley Vineyards offers two refined lodging experiences. The Winery Suites at the Salem Hills Estate feature local artwork, warm wood accents and vineyard views; each stay includes a private winery tour and tasting. Plan ahead and book Into the Woods, a forested campground steps from the winery, where guests can bring an RV or reserve a classic Airstream tucked among the trees.
In the scenic, forested Eola-Amity Hills near Salem, Bryn Mawr Vineyards caters to wine lovers with two upscale lodging options, both offering panoramic vineyard vistas. The bright, contemporary Guest House features two king suites, a full chef’s kitchen and a spacious deck, while the stately Gate House impresses with a 20-foot wood ceiling and a striking wine-barrel chandelier.
Near Eugene, Sarver Winery’s elegant two-bedroom guest house sits atop a hill overlooking vine-covered slopes. After a day of wine tasting, guests can unwind as mist drifts through the vineyard, enjoying Jacuzzi tubs and board games. For a more off-the-grid escape, Lumos Wine Company in Philomath offers a woodsy getaway in a cabin dating back to the family farm’s dude-ranch era in the 1930s.
Cozy Cottages and Historic Homes in Southern Oregon
Just outside the artsy town of Ashland, near Oregon’s southwestern border, Weisinger Family Winery offers a thoughtfully reimagined 1900s farmhouse, now a modernized bungalow. Enjoy an outdoor hot tub and expansive vineyard views — creating an ideal setting for sipping the estate’s hearty reds.
In the heart of the Applegate Valley west of Medford, Troon Vineyard & Farm’s three-bedroom Vineyard House sits beside rolling vineyards with the Siskiyou Mountains rising as a dramatic backdrop. Distinctive as both a winery and working farm, Troon is further defined by its Demeter Biodynamic and Regenerative Organic certifications. Guests are encouraged to wander through native gardens where interpretive signs explain how plants are transformed into biodynamic soil preparations.
Minutes from historic Jacksonville, Rellik Winery’s Rellik House has three suites overlooking its 15-acre vineyard and farm, home to a friendly — and photogenic — herd of alpacas and llamas. Perks include a seasonal pool and hot tub, plus on-site dining. The winery’s culinary program pairs estate wines with savory bites like pear and prosciutto pizza, best enjoyed around flickering fire-pit tables.
For luxe countryside charm, nearby Hummingbird Estate delivers. The 1926 historic home offers five elegantly designed suites — one even includes an enclosed reading porch. Opt for the hillside vineyard cottage and enjoy a spacious terrace and state-of-the-art kitchen. In winter the estate hums with community gatherings like Soup Club and “Pinot and Pages,” where writers convene with laptops and glasses in hand.
