Best Weekend Getaways in Oregon
Oregon is a place where romantic weekend getaways come naturally with its dramatic coastlines, dense evergreen forests, mist-covered mountain peaks, vineyards in gentle valleys, and towns with handcrafted charm. As much as we love being in Portland, getting away for a weekend for me is a must. Whether you crave the sound of waves crashing, the hush of old trees, or extraordinary views in remote quiet, Oregon delivers.
Picking where to stay is part of the romance, maybe a cliff-side lodge with ocean views, a stylish spa resort in the Willamette Valley, a rustic cabin near Mt. Hood with snow-touched pines, or a cozy B&B in a coastal town where you can fall asleep to the sound of the surf. Here are some of the most unique & romantic Oregon escapes I found that I think you’ll love for your next weekend away.
1. Cannon Beach and the Hallmark Resort & Spa
This is a romantic and very picturesque coastal escape! I love how Cannon Beach has preserved its small-town charm by focusing on wellness, art, and its natural seaside beauty, rather than succumbing to over-commercialization.
Part of Oregon’s rugged coastline 1 hour 30 minutes from Portland, Cannon Beach is famous for its dramatic shoreline framed by rolling dunes, evergreen headlands, and of course the iconic Haystack Rock rising majestically from the surf. The town itself is filled with boutique galleries, cozy cafés, and clapboard cottages that feel like they belong in a storybook.
I thought that staying at the Hallmark Resort & Spa was one of the best weekend getaways in Oregon. Why? The resort is perched right on the beach with spectacular views of Haystack Rock. The spa was a real treat. I loved the ocean-inspired treatments, saltwater pool, and the warm, cozy vibe. It was an incredibly romantic setting, especially with a fireplace in the room and private balconies overlooking the waves!
- Check prices at Hallmark Resort & Spa
- Location: Map & Directions
As a big plus, fresh coastal cuisine, from seafood chowder and crab to artisan chocolates and wine tastings, the food was as memorable as the views.
2. Port Orford & WildSpring
With rugged headlands, windswept beaches, working fishing docks, and an unhurried pace of life, Port Orford feels like stepping into a secret world where ocean, forest, and art harmonize beautifully.
We drove 4 hours 50 minutes from Portland to Port Orford, the oldest town on the Oregon coast founded in 1851. I stopped at Battle Rock Wayside Park (there is a visitors center), where settlers first clashed with Indigenous people in 1851, then toured the Port Orford Lifeboat Station Museum (built 1934, free entry) with views over the ocean cliffs. We hiked through Cape Blanco State Park in September this month to its iconic lighthouse, admired the dramatic sea stacks from Battle Rock Wayside, and lingered on deserted beaches.
Staying at WildSpring Guest Habitat, an enchanting eco-retreat set in a serene coastal forest overlooking the Pacific was amazing. The cozy cabins felt like luxury treehouses, blending rustic charm with spa-like comfort. I adored the outdoor hot tub perched on a bluff (shown in the photo) where I could soak under the stars with nothing but the sound of the ocean and whispering trees.
- Location: Map & Directions
3. Bend, Oregon & Tetherow
I love how Bend has preserved its laid-back, outdoorsy charm by celebrating wellness, nature, and adventure, rather than turning into a polished ski-only destination.
I explored the trails and lava landscapes of Newberry National Volcanic Monument, kayaked on the pristine Cascade Lakes, wandered through Drake Park along the river, sipped local craft beers in the “Beer Town USA” scene, and enjoyed stargazing under Bend’s famously clear night skies.
Just 10 minutes west from downtown Bend we found Tetherow, surrounded by sweeping high-desert views and pine forests. The resort’s blend of mountain-lodge style and modern elegance was perfect for a romantic stay. I especially loved relaxing in the heated outdoor pool and hot tubs after a day of hiking, and the incredible dining with a focus on locally sourced ingredients.
I enjoyed starting my mornings with coffee on the terrace before heading out for a round of golf on the award-winning David McLay Kidd course, which was both challenging and spectacular.
I treated myself to dinner at Solomon’s, the resort’s fine-dining restaurant. I also liked that the resort offered endless activities—mountain biking trails, hiking, a fitness center, and a pool—so every day felt exciting and full of possibilities.
- Check prices at Tetherow
- Location: Map & Directions
Bend and Tetherow are among my top Oregon weekend getaways. Why? I found Tetherow equally perfect for a romantic getaway or a family trip, with spacious vacation homes available alongside the hotel rooms.
4. Astoria & Cannery Pier Hotel
I felt a sense of wonder the moment I arrived at Cannery Pier Hotel & Spa in Astoria, Oregon, perched right on the Columbia River. Who wouldn't want to spend a night right over the water? Yes, here every room has a view of the water!
A 40-minute drive from Cannon Beach dropped us at the mouth of the Columbia (1 hour 50 minutes from Portland). I walked along the Astoria Riverwalk, stopping to watch sea lions on the docks, then crossed the 4.1-mile Astoria-Megler Bridge (the longest continuous truss bridge in North America). A side trip took us to Fort Stevens State Park (4,300 acres, $5 day pass) to see the rusting wreck of the Peter Iredale (1906).
I loved how my room at Cannery Pier Hotel came with a fireplace, soaking tub, and a private balcony, and my favorite part was watching ships pass by so close by. I enjoyed the complimentary wine and cheese reception, treated myself to a massage at the spa, and I liked that the hotel provided vintage cars to shuttle guests into town. We also appreciated the hearty breakfast each morning that got us ready to go and explore on our weekend trip!
- Check prices at Cannery Pier Hotel & Spa
- Location: Map & Directions
I found the hotel equally perfect for a romantic getaway or a quiet solo retreat, with an atmosphere that balanced coziness and sophistication. I've been recommending it as one of the best weekend getaways in Oregon since my second visit last year.
5. Ashland & Lithia Springs Resort
I felt a magical sense of calm the moment I arrived at Lithia Springs Resort in Ashland, Oregon, surrounded by lush gardens and the gentle promise of its healing mineral waters.
We drove about 25 minutes south from Medford to Ashland, a mountain town known for its arts and history. Downtown, I walked to the Ashland Plaza with its 19th-century buildings, then popped into the Schneider Museum of Art (free admission on SOU’s campus). A highlight was the Lithia Fountain, bubbling with mineral water since the 1910s. In the evening, we caught a play at the Oregon Shakespeare Festival.
I loved how my room for two nights at Lithia Springs Resort blended cottage-style charm with modern comfort, complete with a fireplace, soaking tub, and plush bedding, and my favorite part was the private patio that opened onto flower-filled paths.
I enjoyed soaking in the resort’s mineral-rich whirlpools, treated myself to the on-site spa, and starting my morning with the complimentary breakfast buffet. I thought the peaceful gardens were a real hidden gem, loved the hammocks, and all the sitting areas scattered across the property.
Osteria La Briccola serving Italian dishes in Ashland was perfect for a romantic dinner.
- Check prices at Lithia Springs Resort
- Location: Map & Directions
I left knowing Lithia Springs Resort was a brilliant idea for anyone seeking a unique blend of relaxation, natural healing, and charming hospitality in southern Oregon.
6. Arch Cape Inn & Retreat
We felt a magical sense of seclusion when we arrived at Arch Cape Inn & Retreat on the Oregon coast, tucked between the mountains and the ocean in a setting that felt both peaceful and romantic.
We drove just 10 minutes south from Cannon Beach (5 miles on US-101) to Arch Cape, a tiny village tucked against the ocean and forest.
I loved how the inn looked like a European château, with turrets, stonework, and lush gardens, and my favorite part was how unique and storybook-like the whole place felt. Our room for the night had a cozy fireplace, plush bedding, and ocean views.
I started each day with a complimentary gourmet breakfast, explored the quiet beaches just steps away.
- Check prices at Arch Cape Inn & Retreat
- Location: Map & Directions
I found the inn equally perfect for a romantic getaway or a personal escape, with spaces designed to inspire relaxation and reflection.
7. Crater Lake National Park
Nestled in the southern Oregon Cascades, Crater Lake National Park is one of the most awe-inspiring natural treasures in the United States. Its impossibly blue waters (the deepest lake in the country!) are framed by sheer cliffs and forested peaks, creating a dreamy scene that feels almost otherworldly. Nearby Diamond Lake is a quieter, more intimate setting, surrounded by pine forests and mountain views that invite relaxation and exploration in equal measure.
After we drove 4 hours from Portland to Crater Lake in August, we hiked the Rim Drive around Crater Lake, gazed down at Wizard Island, took a boat tour across the lake, and stargazed under super dark night skies. The historic Crater Lake Lodge was wonderfully scenic when I visited this month but if you want a view of the lake I recommend booking months in advance.
- Check prices at Crater Lake Lodge
- Location: Map & Directions
8. Portland and the Kimpton Vintage
If you are flying into Portland and exploring Oregon from there, I recommend a stay at the Kimpton Hotel Vintage because it's such an effortlessly cool urban escape! This stylish boutique retreat in downtown Portland has playful wine-country touches. I loved my chic room themed after a local vineyard, and the nightly wine hour that felt both convivial and romantic.
- Check prices at Kimpton Hotel Vintage Portland
- Location: Map & Directions
The rooftop game lounge and easy walkability to downtown hot spots made the Kimpton Hotel Vintage the perfect urban escape.
Conclusion
If you are looking to get away for the weekend, I think the above ideas are super! You can even stay in a couple of different hotels if you want to be more active.
More to explore...
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
