: Courtesy of Steamboat Inn

Luxury Getaways in Southern Oregon

October 18, 2021

Luxury doesn’t have to mean five-star hotels and white-tablecloth dining. In fact, luxury can simply mean living your best life, indulging in whatever makes you happiest — whether that be world-class wine or golf, paddling the rapids of a Wild and Scenic river or taking a guided snowshoe trip through the pristine wilderness of Crater Lake. You can find it all amidst the wildly diverse landscapes and friendly communities of Southern Oregon. Here are some trip ideas to consider booking for now or next season when you’re looking for something with a little extra sparkle.

A cozy bed is and tub are in a wood-paneled room
Find rustic luxury just steps from the Umpqua River at the Steamboat Inn, a haven for fly-fishers, mountain bikers and other outdoor adventurers. (Courtesy of Steamboat Inn)

Whitewater and Waterfalls in the Umpqua Valley

Play: With more rapids per mile than any other Oregon river, the Wild and Scenic Umpqua, north of Crater Lake, is a thrill seeker’s dream. The turquoise waters are home to exceptional Class III and IV whitewater and are truly stunning, with volcanic towers over the canyons and riverside trails for hiking and mountain biking. Book an all-inclusive rafting trip with a local guide like Orange Torpedo Trips, based in Merlin. Their popular Whitewater and Waterfalls package (during the season, May through August) offers two days of rafting and a third day of waterfall touring, swimming holes and possibly hot springs — as well as tent-glamping overnights. 

Eat: Find Victorian elegance at the Parrott House, an 1891 home turned restaurant listed on the National Register of Historic Places. Opt for a wood-fired pizza or a five-course tasting menu of the seasonal farm-to-table cuisine with local wine pairings. Enjoy seating inside the gorgeous space or on the lovely outdoor pavilion, and don’t forget a cocktail from the bourbon bar. 

Stay: Steps from the sparkling North Umpqua River, the Steamboat Inn has been a haven for fly-fishers, hikers, cyclists and others looking for adventure surrounded by pristine beauty. Spend the night in a rustic riverfront cottage, enjoy your morning coffee out on the deck, and if you’re staying between May and October, mosey over to the inn’s restaurant for a hearty breakfast to fuel up for your next day of adventure. 

A picnic table is set with wine and nice dishes
Sit back, relax and let Rogue Picnics literally set the table for you when you're looking for an Insta-worthy, nature-inspired ambiance. (Courtesy Danny Hall)

Luxury Picnics, Private Wine Tastings and a Vineyard Stay in the Rogue Valley

Play: Picnics when you were a kid meant daydreaming under the clouds, splashing in the lake or playing games under a shady oak. Rogue Picnics creates those same kinds of carefree experiences, bringing the ready-made event (canopy, table, comfy seating and amenities) to blissful locations like a local pumpkin patch or pear orchard so you can truly enjoy the time with your loved ones. You can dive into the season with fun add-ons: Nothing says fall like a plate of pumpkin-spice cupcakes, pumpkin-spice lattes, or a fall cheese and charcuterie board. During the cooler months, look for their luxury indoor events too. 

A trip to the Rogue Valley wouldn’t be complete without wine tasting, so why not glam it up with a private tasting or two? Irvine & Roberts Vineyards in Ashland offers curated tastings and spectacular views, while less than 20 minutes north in Medford, Fences Winery and Grestoni Vineyards offer private pairings with the owners.

Eat: One of the region’s must-visit spots for inventive, elevated, hyperlocal dining is at MAS Ashland, named for the Spanish word for “more.” Book a reservation for a special-occasion Cascadian feast by MAS’ chef/co-owner, Josh Dorcak, and consider checking out its sister restaurant, Nama Ashland, which focuses on oysters and other fresh seafood paired with sake, sparkling wines and crisp lagers.

Stay: It could be wine o’clock anytime when you’re staying overnight at a vineyard, just steps from the tasting room. The Rogue Valley is home to several lovely vineyard stays including Hummingbird Estate in Central Point, Weisinger Family Winery in Ashland and Troon Vineyard in Grants Pass. Other indulgent options include the restored 1925 Ashland Springs Hotel — located downtown just steps from the Oregon Shakespeare Festival — and Lithia Springs Resort, a spa-like retreat with mineral waters just 2 miles north of downtown. 

Two snowshoers at Sky Lakes
Snowshoe in Klamath County to your heart's content before warming up by the fire with a warm beverage. (Courtesy of Sky Lakes Wilderness Adventures)

An Enchanted Snowshoe Tour in the Klamath Basin

Play: Let the experts at Sky Lakes Wilderness Adventures guide you along the pristine wilderness of Crater Lake (December through April, weather permitting). Opt for a three-hour snowshoe tour or a three-day backpacking tour, or customize your own trip to explore the wintry landscape and learn about the local geology, wildlife, culture and history. The tour is open to ages 12 and up, with snowshoes and poles provided. Sorry, Fido needs to stay at home. 

Eat: Less than an hour south of Crater Lake, you can warm up with a petite filet mignon and local pinot noir — or a Black Angus burger and local ale — at the Ruddy Duck Restaurant, which anchors the Running Y Ranch Resort in Klamath Falls.

Stay: Set on 3,600 acres with views of the Cascade mountains, the Running Y Ranch Resort offers a host of upscale accommodations including chalets and custom homes. There’s also a full-service spa, the only Arnold Palmer-designed golf course in Oregon, and easy access to family-friendly skiing, snowmobiling, ice skating and other cool-weather fun.

Wooden beams mark the entrance to a rustic saloon
Cowboy Dinner Tree is a classic Oregon Outback experience if you like to indulge in huge portions of food and an unforgettable night sky. (Courtesy of Jak Wonderly/Travel Southern Oregon)

Hang Gliding, Stargazing and Steaks in the Oregon Outback

Play: Lakeview is known as the hang-gliding capital of the West, due to the wide-open skies, and you can take a full-day lesson along with three friends at Oregon Hang Gliding School or another outfitter to get a glimpse of it firsthand. If you’d rather take in the skies from the ground, you’re in luck: Lakeview is also one of the best places in the U.S. for stargazing, thanks to the pristine night sky, nearly free from artificial light. 

Eat: There are just two main choices at Cowboy Dinner Tree in Silver Lake: steak or chicken. Guests can choose between a 26-ounce or 30-ounce top sirloin or a whole roasted chicken, both done the same way the restaurant has been doing it for nearly 30 years. That’s just the way the adoring fans like it. The food here isn’t the only thing that’s legendary — the sunsets sinking into the high-desert horizon are pretty spectacular too. 

Stay: Aspen Ridge Resort in Bly is a dude ranch set on 14,000 acres of Oregon’s Fremont-Winema National Forest. If solitude is your idea of luxury, it doesn’t get more luxurious than this: mountain lakes, wildflowers, elegant log cabins and lodge rooms, and no need to go far for supper if you’d rather stay in. Sidle up to a barbecue dinner at the lodge restaurant and call it a day well spent. Or for something more dramatic, glampers may want to consider booking a stay at the recreation cabin Drake Peak Lookout (open June 15 to Oct. 15), deep in the forest, 25 miles northeast of Lakeview. Book early for the best availability. 

About The

Jen Anderson
Jen Anderson is a longtime journalist and travel writer/editor who is now Travel Oregon’s Content & Community Manager, helping to align content for visitors via social media, print and web. She’s called Oregon home for 25 years and loves finding the latest places to eat, drink and play around the state with her husband and two boys. Brewpubs, beaches and bike trails top the list.

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