This article appears in print in the May 2019 issue, as part of the Wine Country Getaways cover story. Click here to subscribe.

Walla Walla, Washington

Sleight of Hand Cellars
This Walla Walla winery’s passion for magic, rock ’n’ roll and winemaking looms large in everything it does, which is why its three-bedroom, two-bath guesthouse next to the winery is evocatively named The Magician’s Lair. It’s only available to club members (but don’t worry, there aren’t any trapdoors). 1959 J B George Road, 509.525.3661; sofhcellars.com

Armstrong Family Winery
Join the club and you can rent the adorable single story farmhouse with a wraparound porch for 20 percent off. Perched under a grove of shade trees and just steps from the estate vineyard and the family’s main house, the two-bedroom cottage sleeps four people. Bonus: It’s a short drive to downtown Walla Walla.
292 Van Ausdle Lane; 509.520.8975; armstrongwinery.com or wallawallavacationrentals.com

Basel Cellars 
When a simple cottage just won’t do, how about a mansion? The Basel Cellars Estate mansion in Walla Walla boasts 14,000 square feet (eight bedrooms, four full baths, two half baths) of river rock and rustic wood grandeur. It comes complete with a movie theater, gigantic swimming pool and waterslide, and a 2,000-square-foot master suite. Wine club members get a 10 percent discount. But if the $2,000-a-night fee is still too rich, members can compete for a chance to win a stay during the Wine Club Stomp Harvest and Pool Party.
2901 Old Milton Hwy.; 844.561.1782; baselcellars.com or vrbo.com/409954

Dayton, Oregon

Stoller Family Estate
Situated on the winery’s rolling hills are three guesthouses perfect for large families or groups. The Wine Country Cottage sleeps as many as six, the Estate House sleeps eight, and the Wine Farm House sleeps as many as 12. The tasting room is a short stroll away, and wine club members can get a 20 percent discount on guesthouse bookings.
16161 NE McDougall Road; 503.864.3404; stollerfamilyestate.com

Vineyards and orchards are on view from the guesthouses at Red Ridge Farms. Photo by Alan Weiner Photography

Red Ridge Farms
This Dayton destination is known as much for its olive orchards, lavender fields and lush nursery as it is for its Durant Vineyards, so you know the views from this winery’s two guesthouses are beautiful from every angle. Members get discounts ranging from 10 percent to 25 percent on all purchases, which includes lodging. The Garden Suite, perched above the gift shop, sleeps two, while the wood-shingled Stoneycrest Cottage offers two bedrooms and two bathrooms, making it perfect for two couples.
5510 NE Breyman Orchards Road; 503.864.8502; redridgefarms.com

Domaine Serene
With its grand Tuscan-style clubhouse, members-only lounge, multicourse tasting menus and helicopter tours, Domaine Serene is the most over-the-top of the Willamette Valley’s wineries. So, it’s not really a surprise that it runs its wine club membership like a credit card rewards program. Members earn points on purchases, which they can redeem for treats such as stays in the members-only guesthouses on the Dundee Hills property.
6555 NE Hilltop Lane; 503.864.4600; domaineserene.com

Archery Summit
With vaulted ceilings, a deck offering sweeping vineyard views and three bedrooms that sleep a total of eight guests, Archery Summit’s luxury guesthouse is perfect for groups on a getaway. It’s perched on a hilltop overlooking the winery’s Red Hills Vineyard, and just a few minutes from the cute town of Dundee. Wine club members get a 10–50 percent discount, depending on their level of membership. Dayton, 18599 NE Archery Summit Road; 503.714.2030; archerysummit.com or vrbo.com/1060172