Top Southern Oregon Vacations
Running Y Ranch
Klamath Falls, Oregon
Resorts like that in our No. 1 spot make us secretly wish for bullet points – how else to tie up such wide-ranging details in one complete and tidy package? But we’re no quitters, so we’ll proceed with this... read more
Resorts like that in our No. 1 spot make us secretly wish for bullet points – how else to tie up such wide-ranging details in one complete and tidy package? But we’re no quitters, so we’ll proceed with this friendly caution: Running Y Ranch is much grander than it appears!
As you step out onto your Running Y Ranch cabin porch and gaze at the vast meadow and mountain vistas that stretch out before you, it’s easy to imagine that the views were created solely for your Southern Oregon vacation. No big city smog to choke out the crisp, cool mountain air. No ambient light to disguise Oregon’s star-filled skies. And an unexpected dash of luxury – well, it won’t be so unexpected after your stay at this Southern Oregon ranch resort. It’s no wonder Klamath Falls, home of the Running Y, was recently named one of the top 100 places to live. And one stay at this Klamath Falls resort is all it takes to understand why so many have turned the Southern Oregon vacation of their dreams into a permanent address. More than 9,000 acres of unspoiled Oregon meadows, ponderosa pine forests and majestic Cascade Mountain peaks. A Craftsman-style lodge, appointed with timbered ceilings, flagstone floors and stone accents in all the right places. And a Southern Oregon vacation experience that somehow enhances it all!
Feeling inspired on your Southern Oregon romantic getaway? Plan your special day at Running Y Ranch, a naturally stunning destination to say “I do.”
Related Onsite Offerings
Day spa, indoor pool, sauna, exercise facility, golf course, golf shop, gift shop, restaurants, walking and biking trails, ranch corrals and more.
The Running Y Ranch offers a series of Cowboy Schools throughout the summer. Learn the arts of roping, sorting, cutting, penning, reining and other fun games on your Southern Oregon vacation.close
The Village Suites at Ashland Hills
Our No. 2 pick brings us to an unexpected, yet wonderful place where modern luxury and the pristine Southern Oregon countryside peacefully coexist. The Village Suites at Ashland Hills even promises its guests a... read more
Our No. 2 pick brings us to an unexpected, yet wonderful place where modern luxury and the pristine Southern Oregon countryside peacefully coexist. The Village Suites at Ashland Hills even promises its guests a “suite” awakening, with a signature tray of juice, coffee, pastries and the morning paper delivered straight to your suite’s door.
Anyone who’s ever played the cult classic Oregon Trail knows that crossing the country in search of a better life comes with its fair share of perils. Here in Southern Oregon, fast-moving rivers like the Columbia demanded fording and miles of imposing Cascade Mountain peaks forced trail-goers to seek alternative routes – including the Applegate Trail, located mere miles from the Village Suites at Ashland Hills. Walk in the footsteps of the early pioneers as you retrace this historic route around Klamath Lake’s shores. Follow your hike with another famous name – ahem, pour – at the Ashland Vineyards, where a delicious assortment of Rogue Valley wines bear Shakespeare’s famous mug. Make sure to fit in time for a tasting, as these delightful Oregon wines are only available at the Ashland Vineyards estate. And no need to worry about your budget; the Village Suites “gas n go” package promises smooth sailing – and big savings – on your Southern Oregon vacation.
2525 Ashland Street, Ashland, OR 97520
A rich Shakespeare merlot is a striking complement to Paradise Lost or other favorites at the nearby Oregon Shakespeare Festival.
The Village Suites at Ashland Hills are owned and operated by Windmill Inns, which also operates vacation properties in Roseburg, OR, and multiple locations in Arizona.close
Ashland Springs Hotel
If Virginia is for lovers, then Southern Oregon is most assuredly for dreamers. From the stirring beauty of the Rogue River Valley to inspired cultural pursuits like the Oregon Shakespeare Festival, our No. 3... read more
If Virginia is for lovers, then Southern Oregon is most assuredly for dreamers. From the stirring beauty of the Rogue River Valley to inspired cultural pursuits like the Oregon Shakespeare Festival, our No. 3 pick brings your Oregon vacation aspirations to full fruition!
Located in the heart of historic Ashland, the Ashland Springs Hotel serves as a luxurious respite for discerning travelers seeking to partake in all that Southern Oregon has to offer. First opened in 1925 as the Lithia Hotel, a two-year renovation restored this beloved Ashland landmark to its former grandeur, while a new name signaled the blending of the hotel’s signature elegance with 20th century comforts. A delicate color palette of apricot and melon hues highlights the suite’s elegant lines. And outside, a gorgeous conservatory gives way to English gardens filled with sweet-smelling blooms. Here, what promises to be a series of romantic moments begins with the Ashland Springs Hotel’s gracious staff, which discreetly places vintage cards and other personal touches to greet you and yours upon arrival. The lobby’s exquisite stained glass panels and polished terrazzo floors greet guests with the same grace – and slight flair for the dramatic – as they did nearly a century ago. And call us crazy, but even the glittering chandelier seems to mirror the twinkle in your loved one’s eye.
The Ashland Springs Hotel’s Oregon Shakespeare Festival Package includes overnight accommodations, two tickets to the Oregon Shakespeare Festival, dinner at the Larks and expanded continental breakfast for two.
The Waterstone Spa, located next door, offers a full menu of pampering spa and salon treatments.
The Ashland Springs Hotel is listed on the National Register of Historic Places and included among the Historic Hotels of America.close
Aspen Ridge Resort
14,000 acres of Southern Oregon nature and a century-old, working cattle ranch come together to offer travelers a real-life Western experience. Aspen Ridge Resort is everything you're looking for when it... read more
14,000 acres of Southern Oregon nature and a century-old, working cattle ranch come together to offer travelers a real-life Western experience. Aspen Ridge Resort is everything you're looking for when it comes to the Wild West: a breathtaking, natural setting, rustic accommodations, and a plenty of exciting outdoor activities that will make you feel as if you're one of the original cowboys. Hop aboard the saddle for a horseback ride around the trails, or head out with the ranch crew to check up on the cattle. With the Fremont National Forest all around, you can also enjoy a day of hiking and mountain biking to take in as much of nature as possible! Cast a line at a nearby lake for a quiet afternoon of fishing, or simply unwind onsite and drink in the refreshing, natural environment. No matter what you choose to do, you can always indulge in a delicious meal at the onsite restaurant. Enjoy everything from country breakfasts to barbecue beef, chicken and ribs, plus some incredible homemade desserts that's sure to satisfy any sweet tooth!
P.O. Box 2, Bly, Oregon 97622
When you need a break from the horseback riding and adventure, head over to the onsite tennis court for a nice game!
Related Onsite Offerings
Aspen Ridge Resort features 1,200 square foot cabins that can accommodate up to six people. sleeps six. With fully equipped kitchens and stunning views, you're sure to feel right at home!close
Grants Pass, Oregon
The rooms at our No. 6 pick may masquerade as your standard hotel room, but there’s nothing ordinary about these views. As for the river it fronts, the glistening waters and riverbanks outside your window... read more
The rooms at our No. 6 pick may masquerade as your standard hotel room, but there’s nothing ordinary about these views. As for the river it fronts, the glistening waters and riverbanks outside your window belong to none other than Southern Oregon’s beloved Rogue River!
Here at the Riverside Inn, each day begins with the gentle rays of Oregon sunshine streaming through your inn room. Your bed’s plush white duvet piled with pillows may tempt you to linger in bed, but the soothing hum of Rogue River waters begs you to reconsider. As you sleepily roll out of bed and step out onto your riverfront balcony with a steaming cup of coffee in hand, kayakers and other passersby lift their hands in greeting. Downstairs, a delicious breakfast – complimentary with your stay – offers ample opportunity to mingle with other inn guests. And after breakfast, the Riverside Inn’s friendly staff is eager to share their thoughts on Southern Oregon’s must-see sights and attractions. The Riverside Inn’s cozy, intimate feel is ideal for celebrating special occasions and sharing quiet moments. With a bottle of bubbly, chocolate truffles and a gourmet dinner - compliments of the inn – the romance package puts the finishing touches on your Southern Oregon romantic getaway.
The Riverside Inn has packages to celebrate any occasion on your Southern Oregon vacation. Choose from a variety of birthday, anniversary and other celebration packages.
The Riverside Inn is one of eight Country House Inn locations throughout Southern Oregon and Southern California.
Related Onsite Offerings
The Lodge Event Center is the largest meeting and event venue in Grants Pass and easily accommodates groups of up to 350 people.close
Lithia Springs Resort and Gardens of Ashland
Something spectacular is brewing – ahem, bubbling – at our No. 7 spot. Home to the region’s only natural mineral hot springs, the Lithia Springs Resort and Gardens is your go-to destination for rest and... read more
Something spectacular is brewing – ahem, bubbling – at our No. 7 spot. Home to the region’s only natural mineral hot springs, the Lithia Springs Resort and Gardens is your go-to destination for rest and relaxation – the natural way – on your Southern Oregon vacation.
Does your work week have you so wound up that you begin to fear you’ll have trouble letting go, even on vacation? Even the most stubborn of day-to-day stresses won’t last a minute against the legendary powers of Lithia Springs Resort’s heated mineral springs. They say time heals all wounds, but if patience isn’t your strong suit you can sidestep time’s slow progress and step into your spa tub to speed up the healing process! The inn pipes these rejuvenating waters into en-suite spa tubs for two, assuring you plenty of privacy on your Southern Oregon vacation. Ashland, OR really comes alive in winter so skip the crowds and make your Southern Oregon escape to Lithia Spring Resorts at the first sign of snow. The steamy mineral waters are even more welcome when the temperatures drop, so turn up the heat with that special someone in your heart-shaped spa tub for two – just one inspired feature of the inn’s Water Tower Suite. Then spoil each other with a day of pampering at the Blue Giraffe day spa, courtesy of the Ultimate Spa Adventure package!
Tour de Golf packages offer two rounds of golf and a cart at the Eagle Point or Quail Point golf courses, a gourmet breakfast each morning and complimentary hors d’oeuvres each afternoon.
No need to leave your four-legged companions behind; The Inn at Lithia Springs is a pet-friendly!
Related Onsite Offerings
With hassle-free parking, catering and a convenient location close to downtown Ashland, Lithia Springs Resort and Gardens is a winning choice for Southern Oregon weddings, meetings and events.close
Callahan’s Lodge & Restaurant
Our No. 8 pick comes with considerable baggage – and we’re not talking Samsonite. That’s not to say this Southern Oregon lodge’s lengthy history is a bad thing; in fact, we can appreciate lodging with a... read more
Our No. 8 pick comes with considerable baggage – and we’re not talking Samsonite. That’s not to say this Southern Oregon lodge’s lengthy history is a bad thing; in fact, we can appreciate lodging with a past – particularly when that past culminates in one of the finest Oregon lodges to be found!
To Don Callahan, our No. 8 spot represented the fulfillment of a lifelong dream. A former sheepherder, Callahan traded his flock for a piece of land way back in the 50s. He carved out a building site from the solid Oregon mountainside with his own two hands and thus, Callahan’s Lodge was born. Though the name – and Callahan’s legacy – remains, the rustic old lodge was later moved to make way for Highway 5. And following a devastating 2005 fire that left little more than a pile of rubble and ash, Callahan’s Lodge and Restaurant was reborn – back and even better than before. Tucked into a pristine alpine setting, Callahan’s Lodge is set in a canyon bordered by the Siskiyou Mountains. Lodge rooms maintain a rustic feel, but you’re hardly roughing it in these Southern Oregon accommodations. Jacuzzis and real wood-burning fireplaces – no flip-a-switch-flames here – offer ample warmth and comfort, while Callahan’s historic restaurant offers live music to accompany its tempting comfort food menu.
Callahan’s Lodge features full banquet facilities for Ashland, OR dining, business meetings and weddings.
Wally, the resident bartender at Callahan’s Lodge, specializes in signature drinks like the Ruby Slipper, Fireside Special, Tree Smacker, Scooby Snack and the Siskiyou Summit.
Related Onsite Offerings
Game room, outdoor dining, pool table, horseshoe pit, waterfalls, nature trails, restaurant, live entertainment and more.close
Seven Feathers Casino Resort
Named one of the top 20 destination resorts in the Pacific Northwest, our No. 9 pick offers unparalleled luxury on your Southern Oregon vacation. Seven Feathers Casino Resort’s all-new deluxe rooms and suites... read more
Named one of the top 20 destination resorts in the Pacific Northwest, our No. 9 pick offers unparalleled luxury on your Southern Oregon vacation. Seven Feathers Casino Resort’s all-new deluxe rooms and suites are a spectacular way to stay on any vacation, but with so many ways to play at this Umpqua Valley resort, you may never need them!
Chances are you came for the casino, but even if you didn’t your fingers will be itching to pull that slot handle, watch the pictures spin ‘round and hear the sweet sounds of coins clinking in the pay slot. If slots aren’t your thing, Seven Feathers Casino has an impressive range of card and table games to tempt you and lady luck alike. From live action Texas Hold ‘Em to roulette and five-card stud, even the most serious casino gaming cravings are satisfied at this Southern Oregon casino resort. First impressions score big with us and the Seven Feathers Casino Resort is a dazzler – even at first sight. The lobby’s polished floors and glistening dark wood columns hint at the luxury that awaits you in your Oregon luxury room or suite. A chic chocolate and turquoise color palette is accented by plush upholstered headboards and wall-mounted flat screen TVs, while rainfall showers and oversized spa tubs add a spa-quality feel to your Seven Feathers suite.
The lobby’s Kabi Café features coffee, ice cream and other on-the-go treats.
The Stix Sports Bar takes its name from the Native Americans and their rich gaming history, starting with a primitive game played with – what else – sticks. The waging was simple – winner took all – but the play cultivated a sense of community among the tribe.
Related Onsite Offerings
The Seven Feathers Gift Gallery is home to exquisite jewelry, accessories, collectibles and other take-home treasures.close
The Windmill Inn of Roseburg
It may be set in the heart of Southern Oregon’s covered bridge territory and named for a whimsical windmill, but there’s nothing quaint about our No. 10 selection. Voted the city’s finest hotel by the... read more
It may be set in the heart of Southern Oregon’s covered bridge territory and named for a whimsical windmill, but there’s nothing quaint about our No. 10 selection. Voted the city’s finest hotel by the Roseburg community, the Windmill Inn of Roseburg offers every comfort on your Southern Oregon vacation.
Friendly service and affordability are two winning characteristics of the Windmill Inn of Roseburg – good news, as you’ll need helpful points (and a fair amount of cash) to fully appreciate all that Oregon’s Umpqua Valley has to offer. Crater Lake – the Gem of the Cascades – is only a few miles down the road. As you gaze out at its sparkling sapphire surface, it’s hard to imagine this Oregon Lake’s shaky beginnings. Born of the remnants of Mount Mazama’s ill-fated demise, the remaining caldera filled with rain and snow, giving the lake its trademark color. The dense fir forests and Cascade Mountain peaks that border the lake make it one of Southern Oregon’s most inspiring, postcard-worthy scenes. It may not hold a candle to Crater Lake, but the Windmill Inn’s swimming pool offers a wide-eyed beginning to every morning on your Southern Oregon vacation. Join family and friends for breakfast after a dip in its refreshing waters, or have the inn’s gracious staff bring the breakfast greetings to you with a tray of coffee, juice and muffins delivered to your Oregon inn room’s door.
1450 Mulholland Drive, Roseburg, OR 97470
The Windmill Inn of Roseburg offers 780 sq. ft. of meeting room space accommodating groups and meetings of up to 75 people.
The Umpqua National Forest comprises nearly 1 million acres at the foot of the Cascades.close