Oregon Weekend Getaways

Craving mountains, coastlines, and charming small towns? I get it, I was too. That’s why I started exploring Oregon one weekend at a time, and honestly, each trip felt like a breath of fresh Pacific Northwest air. In this post, I’ll share the unforgettable weekend getaways I’ve discovered across the state. I’ve been covering getaways in Oregon for 30 years, which makes me a true local expert.

Where rugged coastlines, misty forests, and cozy little towns make it easy to unplug and recharge. These weekend trips are packed with the most stunning scenery, inviting places to stay, and top outdoor adventures that leave you feeling refreshed and inspired.

Oregon is one of the best states for weekend getaways, and it’s become one of my favorite places for adventure, relaxation, and natural beauty.

Whether you’re strolling the best beaches along the Oregon Coast, exploring the unique charm of Portland, or discovering the underrated beauty of Bend and Ashland, this state has something for everyone. That’s why Oregon is consistently ranked among the best getaway spots in the Pacific Northwest, and why so many of its destinations have become my favorite escapes.

The best part is the variety: coast, mountains, rivers, and wine country. Think weekends filled with the best hiking trails, unique farm-to-table dining, and underrated small towns where you can slow down and relax. These details are what make Oregon weekend getaways both unique and some of the best in the region.

With destinations just a few hours apart, it’s easy to plan the best kind of road trip or short stay. Whether you’re after outdoor adventure, cultural highlights, or cozy relaxation, Oregon offers the best settings for an unforgettable weekend.

Which Oregon getaway will you choose? If you’re searching for the best mix of scenery, charm, and adventure, these weekend destinations deliver. They’re not just trips, they’re the best, sometimes underrated, always unique, and forever some of my favorite escapes in the Pacific Northwest.

Best Oregon Weekend Getaways:

Cannon Beach Bliss at the Hallmark Resort & Spa - 1 hour 30 min from Portland, Oregon

We drove about an hour and a half northwest from Portland to Cannon Beach, a classic Oregon seaside town. I explored the downtown streets lined with galleries and saltwater taffy shops, then stopped at the Cannon Beach History Center & Museum (free entry), featuring a replica of a 19th-century longhouse and artifacts from shipwrecks. Of course, the real highlight was Haystack Rock, a 235-foot sea stack rising from the beach, formed 15–16 million years ago.

After a long day exploring, I felt an immediate sense of relaxation when I arrived at Hallmark Resort & Spa, with its prime oceanfront location and the sound of waves crashing just outside—it was a magical way to begin my stay.

I loved how my room had a fireplace, a private balcony, and panoramic views of the Pacific Ocean, and my favorite moments were watching the sun set over the horizon wrapped in a cozy blanket.

I enjoyed the complimentary fresh-baked cookies in the lobby each afternoon, which added such a joyful and welcoming touch to the experience.

I treated myself to a spa day, where a soothing massage and tranquil atmosphere left me feeling refreshed and restored in the coolest way possible.

I liked starting my mornings with long walks along the wide sandy beach right outside the resort—it felt like a hidden escape where I could clear my mind and breathe deeply.

I appreciated the on-site restaurant, where fresh seafood and hearty dishes were served alongside ocean views, making each meal feel special and memorable.

I also enjoyed the indoor saltwater pool and hot tub, perfect for winding down after a day of exploring the Oregon coast.

I found the resort equally perfect for a romantic getaway or a family trip, with thoughtful amenities that worked for every kind of traveler.

I left knowing Hallmark Resort & Spa was a brilliant idea for anyone seeking a gem of a coastal retreat that blends comfort, relaxation, and unforgettable oceanfront views.

Check prices at Hallmark Resort & Spa

Port Orford Quiet & WildSpring Calm - 4 hours 50 min from Portland

We drove about 40 minutes south from Bandon to Port Orford, the oldest town on the Oregon coast. I stopped at Battle Rock Wayside Park, 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.

I felt an unusual sense of peace as soon as I arrived at WildSpring Guest Habitat in Port Orford, Oregon, surrounded by towering evergreens and the quiet beauty of the southern coast.

I loved that the resort featured just a handful of cozy cabins tucked into the forest, and my favorite part was how private and serene everything felt—it was like having the woods all to myself.

I enjoyed the outdoor hot tub perched on a bluff overlooking the Pacific Ocean, and soaking there at sunset was truly a magical experience I’ll never forget.

I liked the thoughtful details in my cabin—luxury linens, artwork, and eco-friendly touches—that made the space feel both rustic and refined in the coolest way possible.

I appreciated the complimentary breakfast baskets each morning, filled with fresh fruit, baked goods, and other treats, which gave my day a joyful and nourishing start.

I spent my afternoons exploring Port Orford’s beaches and trails, knowing I could return to the peaceful sanctuary of the habitat whenever I needed to recharge.

I also discovered hidden hammocks and quiet garden paths scattered around the property, perfect for reading or simply listening to the sounds of the forest.

I found the staff warm and welcoming, offering recommendations while still respecting the privacy and tranquility that made this place so special.

I left knowing WildSpring Guest Habitat was a brilliant idea for anyone seeking a gem of a coastal retreat where nature, comfort, and serenity all come together in perfect harmony.

Bend Horizons & Tetherow Calm

We drove just 10 minutes west from downtown Bend to Tetherow. This resort area blends history and modern luxury. Bend itself began as a logging town in 1905, and you can still see remnants at the Deschutes Historical Museum downtown ($6 admission).

I felt a magical sense of space and freedom the moment I arrived at Tetherow Resort in Bend, Oregon, surrounded by high desert landscapes and sweeping Cascade Mountain views.

I loved how my room blended modern design with warm, natural touches—plush bedding, a fireplace, and a private balcony—and my favorite part was watching the sun dip behind the mountains each evening.

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, where creative dishes paired with local wines made for a joyful culinary experience.

I 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.

I appreciated the little luxuries too, like the fire pits where I could unwind under the stars, and the friendly staff who made everything feel seamless.

I also discovered how close the resort was to downtown Bend, breweries, and the Deschutes River, making it the coolest base for exploring both nature and city life.

I found Tetherow equally perfect for a romantic getaway or a family trip, with spacious vacation homes available alongside the hotel rooms.

I left knowing Tetherow Resort was a brilliant idea for anyone wanting a gem of a Central Oregon escape that blends outdoor adventure with modern comfort and unforgettable views.

Check prices at Tetherow

Astoria Waters & Cannery Pier Quiet - 1 hour 50 minutes

The 40-minute drive from Cannon Beach dropped us at the mouth of the Columbia. I walked along the Astoria Riverwalk, stopping to watch sea lions barking 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 felt a magical sense of wonder the moment I arrived at Cannery Pier Hotel & Spa in Astoria, Oregon, perched right on the Columbia River with water and sky stretching endlessly around me.

I loved how my room came with a fireplace, soaking tub, and a private balcony, and my favorite part was watching ships pass by so close it felt like I could almost touch them.

I enjoyed the complimentary wine and cheese reception in the evenings, which made for a joyful way to unwind while taking in the spectacular river views.

I treated myself to a massage at the spa, where the calm atmosphere and attentive care left me feeling completely restored in the coolest way possible.

I liked that the hotel provided vintage cars to shuttle guests into town—it was such a unique and fun touch that added to the experience.

I appreciated the hearty breakfast each morning, with fresh options that fueled me for a day of exploring Astoria’s history, shops, and waterfront.

I spent time just walking the pier itself, savoring the salty air and the unusual experience of being surrounded by the river on all sides.

I found the hotel equally perfect for a romantic getaway or a quiet solo retreat, with an atmosphere that balanced coziness and sophistication.

I left knowing Cannery Pier Hotel & Spa was a brilliant idea for anyone wanting a gem of a riverside stay that blends luxury, history, and unforgettable views of the Columbia River.

Check prices at Cannery Pier Hotel & Spa

Ashland Springs & Lithia 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 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.

I loved how my room 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, which felt restorative and joyful, leaving me refreshed and relaxed after a day of exploring.

I treated myself to the on-site spa, where soothing treatments and a serene atmosphere made it the coolest way to connect with the resort’s focus on wellness.

I liked starting each morning with the complimentary breakfast buffet, filled with fresh, locally inspired options that set a delicious tone for the day.

I appreciated the peaceful gardens, hammocks, and hidden sitting areas scattered across the property, which felt like gems waiting to be discovered.

I also loved exploring nearby Ashland, from boutique shops to wine tasting, and of course the renowned Oregon Shakespeare Festival, knowing I had such a tranquil retreat to return to.

I found the resort equally perfect for a romantic getaway or a restorative solo escape, offering spaces to unwind, reflect, and recharge.

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.

Check prices at Lithia Springs Resort

Arch Cape Inn & Retreat

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.

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.

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.

I enjoyed staying in a room with a cozy fireplace, plush bedding, and ocean or mountain views that made every moment feel special and serene.

I started each day with a complimentary gourmet breakfast, lovingly prepared and served in the elegant dining room, and it was such a joyful ritual that set the tone for the day.

I liked exploring the quiet beaches just steps away, where I often found myself alone on the sand, which felt like a hidden gem compared to the busier spots nearby.

I appreciated the inn’s intimate atmosphere, with thoughtful touches like afternoon wine and snacks, soft music, and warm hospitality that made me feel at home.

I also enjoyed venturing into nearby Cannon Beach and Manzanita, knowing I could return to the inn’s calm and cool retreat afterward.

I found it equally perfect for a romantic getaway or a personal escape, with spaces designed to inspire relaxation and reflection.

I left knowing Arch Cape Inn & Retreat was a brilliant idea for anyone wanting a spectacular coastal stay that blends European elegance with Oregon’s rugged natural beauty.

Check prices at Arch Cape Inn & Retreat

Portland Pause at the Kimpton Vintage

We flew about 4 hours nonstop from Austin to Portland (this is where we usually start our road trip) and touched down in Oregon’s biggest city. Downtown, I toured the Oregon Historical Society Museum ($10 admission) and climbed up to Pittock Mansion (built 1914, $12 entry) for sweeping views of the city framed by Mount Hood. Powell’s City of Books (a full city block of shelves) was a must before dinner.

I felt a magical energy the moment I stepped into Kimpton Hotel Vintage Portland, with its playful design, wine-country theme, and welcoming vibe that made me feel instantly at ease.

I loved how my room blended bold, modern style with cozy touches—plush bedding, a mural wall, and big windows—and my favorite feature was the deep soaking tub that made every evening feel like a spa retreat.

I enjoyed the complimentary wine hour in the lobby each evening, which was such a joyful way to connect with other guests while sampling local Oregon wines.

I treated myself to dinner at the on-site restaurant, where creative dishes paired with craft cocktails made for the coolest dining experience without ever leaving the hotel.

I liked how the hotel celebrated Portland’s playful side, from the lobby’s graffiti-style art to the game lounge with shuffleboard and video games—it felt unusual in the best way.

I appreciated the little touches too, like loaner bikes for exploring the city, pet-friendly perks, and staff who made every interaction warm and personal.

I also loved the central location, just steps from downtown shops, food carts, and theaters, which made exploring Portland exciting and effortless.

I found the hotel equally perfect for a romantic getaway or a fun weekend with friends, offering something for every mood and style of traveler.

I left knowing Kimpton Hotel Vintage Portland was a brilliant idea for anyone wanting a gem of a boutique stay that captures the city’s creativity, comfort, and cool spirit.

Check prices at Kimpton Hotel Vintage Portland

Leaving Oregon, But Not Really

As we packed the car for the final stretch, I looked back one last time, at the pines swaying in the coastal wind, at the distant curve of a trail we hadn’t walked, at the places that had opened slowly and stayed with me long after. Oregon didn’t dazzle with spectacle. It gave me quiet magic: a steaming waffle by a foggy window, the hush of a river path, the sudden clarity of a mountain after days of mist.

Each town offered something gentle, a way to slow down, to look closer, to listen. And each meal, each morning view, each road between was part of that rhythm. The state never rushed me. It simply waited, steady as its trees, soft as its beaches, ready to be noticed.

I left Oregon with a fuller breath. Not everything needs to be loud to be unforgettable.

Hi, I'm Ema. Ready to plan your next weekend getaway? Let me help. I have 30 years of experience, over 400,000 social media followers, and my work as a travel expert has been mentioned on abc6 Morning Show, Best of the Web, USAToday, and many other outlets. When I'm not traveling around the USA, I live in Austin, TX with my husband and son. Click for more.

 

Leave a Comment