The state of Oregon, with its bountiful forests, mountains, and ocean shoreline, is an autumn wonderland. Take advantage of the cool fall weather to experience the state’s outdoor areas without the summer tourists and crowds. Whether you want to go wine tasting on the Applegate Valley Wine Trail, or embark on a hike past waterfalls along Sweet Creek, there’s a perfect Oregon vacation rental for your weekend getaway. As you search for accommodations for Columbus Day, start your research with these friendly towns.
Stay in the heart of Oregon’s wine country in Dundee. From the area’s pastoral vacation rentals, you can wake up with views of the vineyards, many dotted with autumn colors. In town, walk between tasting rooms at Hawkins Cellars, Dobbes Family Estate, and Zerba Cellars. Make the most of the cool fall weather with a stroll through the vines at Cramoisi Vineyard or Thistle Wines.
Find vacation rentals in Dundee
2. Cannon Beach
Explore the rugged Oregon coast from your home base in Cannon Beach. In early October, the howling winds and cool weather create a thrilling atmosphere — as a bonus, crowd levels are low, so you can walk the beach in peace. Bring a rain jacket and head down to the beach to watch the waves pound the shore after an autumn storm. A short drive away, the deep forests and rocky shores of Ecola State Park provide opportunities to see the fall populations of Roosevelt elk and birds that are migrating along the Pacific Flyway.
Find vacation rentals in Cannon Beach
See some of the most beautiful fall colors in the state near Rainrock. Make the short drive south to the Sweet Creek Trail, which winds through colorful maple and alder trees, passes 10 waterfalls, and ends at Sweet Creek Falls. Back at your vacation rental, pick up your tackle box and head to the Siuslaw River to fish the fall chinook run.
Find vacation rentals near Rainrock
Feel like a local on Columbus Day in Silverton, a small town east of Salem. From here, you’re a quick drive from Silver Falls State Park, which is home to some of the state’s most stunning fall scenery. Hop on the waterfall loop trail to walk beneath canopies of changing leaves and past 10 waterfalls. At some points, you can even follow the trail behind a waterfall. In town, see the autumn splendor at the Oregon Garden, or enjoy the views along Silver Creek.
Find vacation rentals near Silverton
Find the perfect Oregon vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!
5. Mt. Hood
Take one of Oregon’s best fall road trips from vacation rentals in Mt. Hood. Drive the 146-mile Mt. Hood Scenic Loop through the Columbia River Gorge, across the slopes of the mountain, and through the Hood River Valley for panoramic views of the changing leaves. Later, see the trees up close with a hike along the Pacific Crest Trail or the Timberline Trail.
Find vacation rentals in Mount Hood
Get out into Oregon’s wilderness on a weekend in Bend. The cool Columbus Day weather is perfect for mountain biking on the Bend-Innes Market Loop or the Three Sisters Scenic Bikeway. For a slower-paced adventure, search for changing leaves on a hike along the Metolius River or up Pilot Butte. Nearby, explore the Lava River Cave without the summer tourists at the Newberry National Volcanic Monument.
The streets of Corvallis glow with color each fall, adding a fun fall twist to every walk. Experience the best colors as you wander through downtown or the campus of Oregon State University. Pioneer Park and Avery Park offer walking trails and views of the Marys River, and the Trysting Golf Club provides views of the leaves from every hole. Bring your bike and head to Bald Hill Natural Area for a mix of singletrack and paved trails.
Find vacation rentals in Corvallis
8. McKenzie Bridge
See the changing leaves reflected in the McKenzie River in McKenzie Bridge, a small community set deep in the wilderness. The best way to experience the season is on the McKenzie River National Recreation Trail. Bring your bike or hiking shoes and take the trail from town and into the surrounding hills. If you feel like driving, drive the McKenzie Pass-Santiam Pass Scenic Byway through stands of brilliant yellow aspens.
Find vacation rentals near McKenzie Bridge
Ashland is at its finest on Columbus Day weekend — the summer heat and crowds are gone, days are sunny and pleasant, and the fall colors add a magical twist to any outdoor activity. Hike Grizzly Peak, try whitewater rafting on the Rogue River, or stroll on the trails at Lithia Park. In the evening, attend the last performances of the Oregon Shakespeare Festival’s season. If you’re still in town on Monday, head over to Southern Oregon University to join in the Indigenous Peoples’ Day celebrations.
Find vacation rentals in Ashland
Enjoy the warm early fall weather on a Columbus Day weekend getaway in Applegate. Situated in the heart of the Applegate Valley Wine Trail, this beautiful spot offers views of the hills, vineyards, and the Applegate River. From local vacation rentals, you can drive to the Trail’s 18 wineries. After you’re done, hunt for early fall colors with a hike along the East Applegate Ridge Trail.
Find vacation rentals in Applegate
In early October, Portland comes to life with brilliant fall colors and cool weather. Head straight for the Portland Japanese Garden to see the spectacular Japanese maples turn orange, or rent a bike from Waterfront Bicycle and pedal along the Willamette River to see the colors around the city. In 2015, Portland adopted Indigenous Peoples’ Day — join in celebrations around the city to watch cultural performances and listen to traditional Native American storytellers.
Find vacation rentals in Portland
Ready to go? Check out these amazing Oregon vacation rentals on Tripping.com.