Whether you’re a local or spending your summer in a Portland, Oregon vacation rental, it can be good to take a break from the urban atmosphere of the city. Luckily, Portland is surrounded by natural beauty and charming towns, giving you plenty of options for hiking, biking, wine tasting, wildlife watching along the coast, or just relaxing in a weekend vacation rental.

Cannon Beach

Hrach Hovhannisyan/Shutterstock

Cannon Beach offers plenty of spectacular views of the Oregon Coast, including the area’s famous rock formations. Spend a relaxing day at the beach and catch glimpses of wildlife such as puffins and crabs. In town, you can hone your artistic sensibilities at a number of galleries or enjoy some seafood at one of the town’s many excellent restaurants.

Local Tip: Make sure you get to the water for sunset, it’s one of the west coast’s most famous views.


Richard Bacon/Shutterstock

Bend is just three hours away from Portland, but it has a completely different feel – sitting just at the edge of coastal rain-forest and high desert. It offers a gateway to the Cascades, giving you plenty of opportunities to get active with hiking, trail running, or mountain biking. You can also kayak, fish, SUP, or swim on the Deschutes River right through town, or up at the numerous lakes in the area. Bend is famous for its breweries, so don’t forget to try one of the local brews before you leave.

Local Tip: Head a little west of town to get quieter access to the beautiful river’s edge.

Hood River


Hood River is an oasis for outdoor enthusiasts of all types. Whether you enjoy windsurfing, canoeing, fishing, hiking or boating, you’re bound to find an adventure in the area. The town is surrounded with farmland, letting you take your pick of fresh fruits and veggies to take home to your vacation rental.

Local Tip: Grab a beer at a brewery, then head to the Hood River event site to watch the kite boarders rip across the Columbia Gorge.

Wine Country

Steven Madow/Shutterstock

If you’re a wine enthusiast, no visit to Portland is complete without a retreat to the Willamette Valley. Williamette Valley’s total geographic area expands for over three million acres, but two cities within the region have the best wineries near Portland: Newberg and Sherwood. This wine region produces excellent pinot noir and pinot gris wines, and it’s much quieter and laidback than big-name wine producers like the Napa Valley. The Willamette Valley is also a wonderful place to sample gourmet meals filled with quality produce.


Jess Kraft/Shutterstock

The port town of Astoria gives you the opportunity to spend your days fishing, sampling seafood or taking in stunning views of the ocean. Its many Victorian houses offer you plenty of ways to get up close and personal with history as you walk around and explore.


Sue A Dunning​/Shutterstock​​

Movie buffs can find plenty to rejoice about in Brownsville, as this small Oregon town was the filming location for “Stand by Me.” Even if you’re not a fan, you can still find lots to do. Brownsville has its roots in the Oregon Trail, so there are lots of historic buildings and sites to visit.


Joshua Rainey Photography​/Shutterstock​​

This college town has no shortage of learning opportunities, from the Oregon Air and Space Museum to the Museum of Natural and Cultural history. Eugene is also a great city for exploring by foot, as it has charming streets and stores galore.


Hills Outdoors​/Shutterstock​​

Golfers, horseback riders, hikers, sport fishers and mountain bikers alike all flock to Sisters, as this town offers outdoor activities for almost any taste. If you’re visiting in the summer, be sure to check out local listings, as Sisters also hosts a variety of festivals and events in the warmer months.

Local Tip: Come into town during the quilt festival, seriously, it’s amazing!

Mount Hood

Josemaria Toscano​/Shutterstock​​

There’s just something relaxing about retreating into the mountains after spending a lot of time in the city. Mount Hood is a ski and snowboard haven, so it’s a popular choice for a winter weekend retreat. If you’re visiting in the summer, you can find lots to occupy your time from golf to hiking around the ridges, and tremendous lakes.

Local Tip: At sunset some of the lakes offer a magnificent reflection of the Volcano looming on the horizon.


Dee Browning​/Shutterstock​​

If you have a beach retreat in mind, head over to Newport for your getaway from Portland. This town gives you access to sandy beaches, where you can relax on the sand, splash around in the waves or play a game of beach volleyball. The town also has a charming harbor, where you can take a pleasant stroll in the evening.