Portland's appeal doesn't end at the city limits. Within a few hours' drive in any direction lie crashing waves, snow-capped peaks, rolling vineyards, and high desert wonders. Pack light but dream big—these Pacific Northwest escapes deliver adventure without burning precious vacation days. Ready to transform an ordinary weekend trip into something legendary? Read on.
Featured vacation rental: Machouse
Tuscany's got competition in Oregon's wine country. Dundee's red-soil hills and McMinnville's boutique tasting rooms offer sophisticated sipping without pretension. Navigate rolling hills dotted with over 700 vineyards and dine at farm-to-table eateries where local produce is the highlight of dishes that complement your new favorite bottle.
Featured vacation rental: Salty Shore
This unassuming beach town serves up vintage Oregon coast—think crabbing off the jetty, beachcombing for agates, and boardwalk ice cream cones eaten to the backdrop of crashing waves. The showstopper? Twin Rocks, iconic sea stacks that punctuate the horizon.
Featured vacation rental: Chinook Chalet
Massive Haystack Rock anchors miles of walkable sand, while the compact downtown packs a serious punch with galleries, boutiques, craft beer spots, and upscale restaurants (where you can still wear a hoodie). Hunt starfish in tide pools, hike Ecola State Park's rainforest trails, and roast s’mores around a beach bonfire.
Featured vacation rental: The Jewel of the Nye
Newport juggles two personalities—working fishing port and tourist haven. Wander the historic bayfront where sea lions bark for attention, then dine dockside on just-caught Dungeness crab. Cross the bridge to explore Yaquina Head's lighthouse and tidepools, before sampling coastal-inspired brews.
Featured vacation rental: Skiing Bear Chalet
Carve through powder at Meadows or Timberline, hike the legendary Timberline Trail, or paddle across Trillium Lake with the mountain reflected perfectly in its waters. Historic villages like Government Camp offer après-adventure fuel, like massive breakfasts and microbrews.
Featured vacation rental: Union Lofts 310
The Gorge delivers nature at its most colossal—80-mile-long canyon walls plunging toward the Columbia River, dozens of waterfalls cascading over basalt cliffs, and winds that create world-class conditions for kiteboarders. After hikes with panoramic views, rest up at Hood River's brewpubs.
Featured vacation rental: Ottertail Cabin
Requiring a longer weekend commitment (and a much longer drive), Wallowa Lake rewards the journey with Oregon's most dramatic alpine scenery. This glacial lake sits at the foot of the Wallowa Mountains—affectionately called "Little Switzerland"—offering crystal-clear waters for kayaking and beaches meant for soaking up the sun.
Featured vacation rental: Gorge View Chalet
This high desert playground delivers 300+ sunshine days annually alongside an endless list of adventures: volcanic cave explorations, world-class rock climbing, paddle-boarding, and mountain biking through ponderosa forests. In between, dive into its legendary craft beer scene.
Featured vacation rental: Golf Home 53
This resort community delivers postcard views of Sisters and Mount Washington from stunning golf courses and tennis courts. Swim in outdoor pools with mountain vistas, then retire to timber-framed lodge vacation homes where floor-to-ceiling windows frame ponderosa pines.
Featured vacation rental: Wildwood Wonder
This planned resort community offers everything from observatory stargazing to white water rafting, horseback riding to craft cocktails. Miles of paved bike paths connect vacation homes to pools, restaurants, and the nature center. Even better: 300 days of sunshine make Portland's rain feel like a distant memory.
