Best Weekend Getaways in Oregon
Searching for the best weekend getaways in Oregon? Well, you are in the right place! Whether you crave the sound of waves crashing, the hush of old trees for 48 hours, or extraordinary views in remote quiet, I think you will love these Oregon spots as much as we did.
1. Cannon Beach and the Hallmark Resort & Spa
This is a romantic and very picturesque coastal escape and I especially 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 enjoyed having interesting things to do nearby, including Ecola State Park, Icefire Glassworks, and the Cannon Beach History Center & Museum.
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 our room as well as our private balcony overlooking the waves!
- Check prices at 3-star 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 at the Hallmark Resort was as memorable as the views.
2. Port Orford & WildSpring
With rugged headlands, windswept beaches, working fishing docks, and an unhurried pace of life, this town 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.
- Location: Map & Directions
What I loved best:
Staying in a cool eco-cabin at WildSpring Guest Habitat surrounded by the forest on one side overlooking the Pacific was amazing, and I adored the outdoor hot tub perched on a bluff (in the photo) where I could soak under the stars while listening to the sound of the ocean.
3. Bend, Oregon & Tetherow
I love how this place has preserved its laid-back, outdoorsy charm by celebrating wellness, nature, and adventure, rather than turning into a polished ski-only destination.
Once we arrived in Bend, 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 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 of our room 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 family vacation, 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 this place! After all, 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 river (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 3-star 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 this resort, surrounded by lush gardens and the gentle promise of its healing mineral waters that completely won me over on our romantic weekend getaway.
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 3-star 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 this romantic inn 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 Arch Cape 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 Lodge
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.
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.
- Check prices at Crater Lake Lodge
- Location: Map & Directions
What I loved best:
I loved our day trip to nearby Diamond Lake which is a quieter, more intimate lake, surrounded by pine forests and mountain views that were incredibly relaxing!
8. Portland and the Kimpton Vintage
This stylish boutique retreat in downtown Portland has playful wine-country touches. I loved my chic room for two days themed after a local vineyard, and the nightly wine hour that felt both convivial and romantic.
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!
- Check prices at 4-star Kimpton Hotel Vintage Portland
- Location: Map & Directions
What I loved best:
The rooftop game lounge and easy walkability to downtown.
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.
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.
5. If you are planning to visit more than three national parks in the next 12 months, buy the America the Beautiful Pass.
