The Rogue Valley offers a wide array of top-notch bed and breakfasts, guest cottages, and hotels. But if you’ve ever wondered what it would feel like to sleep in a vineyard, the following select Southern Oregon wineries invite you to experience unique and indulgent accommodations among the vines! Our journey of discovery will begin in the south and wind northward. With the promise of unparalleled views, free tastings, winery tours, live music, and peaceful surroundings, your perfect choice awaits. All locations are within easy reach of favorite activities—the Shakespeare Festival in Ashland, Britt Music Festival in Jacksonville, fine dining and cultural events in Medford, and a backpack full of call-of-the-wild outdoor activities. Whether your goal is to pack in as much of the flavor of the area as possible or to find the perfect, peaceful escape from it all, sleeping among the vines will only serve to sweeten the package. Pleasant dreams.

WEISINGER FAMILY WINERY—Originally an orchard, Weisinger Family Winery is among the earliest Southern Oregon wineries and is the first to be established in Ashland. The Cottage is a renewal of the original early 1900s farmhouse, providing a cozy getaway for two, nestled next to Pinot Noir vines. Enjoy the valley’s mild climate from the recently remodeled outdoor space with pergola decking, barbeque, and hot tub. This 600 square-foot getaway sits among the Ashland hills. It’s private yet convenient, and just a short walk from the tasting room, where you can sample award-winning wines, complements of the winery. Snuggle next to the gas fireplace on chilly days and nights, and dream away cares in a comfy queen-sized four-poster. Guests also receive a complimentary bottle of wine with a cheese and cracker basket, as well as discounts on all wine purchases made during their stay. This location is perfect when you want a quiet country experience only eight minutes from downtown Ashland. A visit to the Weisinger Vineyard Cottage is truly a memorable experience.

GRIZZLY PEAK WINERY—­A stay at Grizzly Peak Winery in Ashland is all about the views. Their namesake mountain, Mount Ashland, and the town of Ashland, are shown to advantage at every turn. Overnighters reap additional benefits. “Whenever it’s the season, they get the bounty of our fruit trees,” owner Virginia Silbowitz explained. “Apples, pears, and figs. We enjoy sharing it with our guests.” Bring your binoculars, because Grizzly Peak is also prime birdwatching territory. Their Sunset Cottage is an 800 square-foot light and airy studio available when there are no weddings or traveling musicians stopping for their summer concert series. It sleeps four and has a full kitchen. Guests are invited to a complimentary evening of music and a food truck meal during concert season. A bottle of red or white and a wine tasting are part of the package. Vineyard strolls are available through eleven varietals. After a tour, enjoy a picture-perfect picnic set within an inviting oak grove. And do meet the friendly resident cats—Rogue and Merlot.

PASCHAL WINERY & VINEYARD—Paschal Winery & Vineyard overlooks the Tuscan-esque hills of Talent, Oregon. Owner, Aga Paschal, shows two Dream Cottages available for lodging, “just 67 steps” from the warm and welcoming tasting room. Both units are unfussy yet lush, with big screen televisions for nights in, fireplaces, and trendy sliding “barn” doors to the bedrooms. King-sized beds from which to watch the sun set, await the end of a perfect day. Views are rich with acres of vines and Roxy Ann peak. Dream Cottage two includes a massage chair in the living room and swinging bed for a playful mood. On the patio, relax into a hammock with a glass of Civita, and soak your cares away under the stars in the hot tub. Guests receive a free tasting, bottle of wine and are welcome to work hands-on in the vineyard depending on the season. Aga is a people person and enjoys her role as innkeeper. “This has been incredible. We’ve made many friends.”

ROXYANN WINERY—­For a centrally-located vineyard stay and for those who crave local history, RoxyAnn Winery in Northeast Medford is a fabulous choice. All estate buildings are listed on the National Historic Register. Originally an apple orchard before the pear gold rush, RoxyAnn remains a 250 acre estate of mostly wine grapes with some pears and a few apples. RoxyAnn offers two smaller units—the Carriage House and, formerly, the Boys’ House, one with single bedroom and kitchenette, the other with sitting room and bedroom, no kitchen. For larger parties and family reunions, consider soaking up the historic charm of their 1920s Big House. Chad Day, fourth generation owner explains,  “This was my great-grandfather’s summer home.” The Big House boasts three master bedrooms, each with sleeping porch and smaller attached bedroom. A large kitchen with butler’s pantry is available. And don’t miss the rustic ambiance of their 1918 tasting room, where they showcase talented local musicians, indoors or out, year-round.  

HUMMINGBIRD ESTATE—A visit to Hummingbird Estate is a stately trek back through valley history to a 1920s manor home on Old Stage Road near Jacksonville. A generous driveway through vines delivers on the stunning refurbished estate, housing spacious yet homey tasting rooms below with five luxury guest suites with private baths above. Rooms are, the Japanese Maple, Chardonnay, Syrah, Pinot Noir, and the largest, Sequoia, with built-in bookcase and writing desk. All suites contain king beds, but the Pinot Noir, with two twins. Accommodations range in size from four to seven hundred square feet and are expertly restored while retaining all the charm of original appointments. Antique, inlaid ceramic tiles and quaint, non-operational fireplaces show sincere appreciation for authenticity. A fireplace downstairs works well for flame gazing. Vintage windows look out onto inspiring country views, and sleeping quarters are tastefully furnished with luxury linens, plush custom bathrobes, and special details to make your time away simply enchanting. And the owners’ daughter, Kristina Alvarez, will cook your breakfast.

RELLIK WINERY—Further along Old Stage Road and a half mile from historic Jacksonville, smiling alpacas bid a friendly welcome to Rellik Winery. Rellik’s red-eyed raven label signifies award-winning wines. Now, a refurbished Rellik House is ready for friends and family getaways.  Rellik House has a common area plus three rooms—the Raven, Wine, and Alpaca. The Raven and Wine suites with one bedroom, Alpaca with three. All have living rooms, kitchenettes, laundry facilities and 55” TVs. They may be enjoyed individually or, why not take over the whole house? Perfect for larger groups, Rellik sleeps up to fourteen. Guests receive money toward a meal from their new farm-to-table kitchen. Plunge into a heated pool after a hard day of sightseeing, then huddle your clan around the fire pit as night falls, with good conversation and a warming glass of Cabernet. “We have it all,” says owner Delando Pegan. “You can stay here, eat here, drink here, you can get married here!”

TROON VINEYARD­—Need to escape the hustle and bustle? A respite at Troon Vineyard is a must. Situated in the breathtaking Applegate Valley, Troon is one of only two certified biodynamic and organic wineries. It’s also the earliest, with grapes originally planted in 1972. Troon has two fully refurbished homes to share—the Cottage House, 1,400 square feet with two bedrooms, two baths, and the Vineyard House, 1,800 square feet with three bedrooms and two baths. New owner (with husband, Bryan), Denise White, showed off these two secluded homes situated literally among the vines. Each is professionally appointed with luxury fixtures and tasteful decorator touches. Everything you could want in a home away from home is included in the price—cookware, spices, laundry soap, even spaghetti and sauce when you arrive hungry. Away from city lights, a dark sky is the ticket for star-gazing and sound sleep. With no shortage of unobstructed views of the verdant Applegate hills, and nearly 100 acres to stroll, including a lake with swans, relaxation is a given.

BOOKSTAYHOP.COM—Need help planning your Southern Oregon visit? Longtime Southern Oregon resident Daniel Perry is your man. Daniel’s online travel agency, BookStayHop.com currently manages over 70 properties in Southern Oregon’s Wine Country, downtown Ashland, Hyatt Lake, Crater Lake, the Oregon Coast and beyond. More than a travel agency, bookStayHop.com serves as a concierge. “We help people plan their entire adventure,” Daniel explains, “including their stays, plays, restaurants, hiking, Crater Lake, etc. We share what we love so much.” Many of the properties welcome guests with gift baskets packed with local treats, including tastings at three wineries. BookStayHop can customize your adventure with multiple overnight locations within perfect proximity to your chosen delights. “We like matching people up to the type of experience they’re looking for,” Daniel says. They care about the local economy. “80 percent of what we source is local. Our whole team gives back.” BookStayHop can arrange as much of your stay as you require from the comfort of your home, leaving you time to anticipate your dream vacation.

©Southern Oregon Wine Scene – from the Spring 2020 issue

Weisinger Family Winery

Grizzly Peak Winery

Paschal Winery & Vineyard

RoxyAnn Winery

Hummingbird Estate

Rellik Winery

Troon Vineyard

BookStayHop.com