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The highest-performing listings in The Dalles.
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Challenging to Investors
STRs are legal but currently constrained: a moratorium blocks new non‑owner‑occupied licenses in residential zones and proposed amendments would impose a cap, a lottery, 300‑ft proximity rules, and enhanced tax compliance. Together, these create significant permitting friction and investment risk despite a modest fee and straightforward process.
Local STR Agent
STR specialist · The Dalles, OR
The Dalles is a small city in north-central Oregon that serves as the county seat of Wasco County, with a population of roughly 15,000 residents. Straddling the Columbia River about 80 miles east of Portland, the town has long functioned as a regional hub for agriculture, river commerce, and travel through the Columbia River Gorge. Its name derives from the French word for the flagstone-like basalt rapids that once roared through the river here, and the city today carries a blend of historic small-town character, working agricultural roots, and a strong outdoors-and-wine-country identity. It is best known as a gateway to the Columbia River Gorge, the surrounding wheat country, and the wineries of the Columbia Valley.
One of the most visited destinations near The Dalles is the Columbia River Gorge National Scenic Area, which begins just west of the city and stretches for more than 70 miles along the river. The scenic area is famous for its towering basalt cliffs, dozens of waterfalls, windsurfing beaches, and the famous Historic Columbia River Highway, all within a roughly 15- to 90-minute drive depending on how far into the gorge visitors travel. A more compact but compelling stop is the Columbia Gorge Discovery Center and Museum, located just west of downtown, which interprets the natural and cultural history of the gorge through interpretive exhibits and an adjacent nature trail. The center is about a 10-minute drive from the city center and serves as a useful orientation point for travelers arriving from the east.
A short drive east of The Dalles, near the community of Maryhill in Washington State, sits the Maryhill Museum of Art, an eclectic museum housed in a former mansion overlooking the Columbia River, about 45 minutes from the city. The surrounding Maryhill State Park and the nearby full-scale Stonehenge replica memorial, a World War I monument built by the same entrepreneur who created the museum, draw additional visitors to the area. Closer to town, the historic downtown core of The Dalles includes well-preserved late-19th and early-20th-century buildings, riverfront walking paths, and a small but active arts and dining scene, while the nearby Fort Dalles Museum and surrounding park offer a glimpse into the region's pioneer and military past.
For short-term-rental owners and guests, The Dalles offers an appealing combination of small-city amenities, walkable historic streets, and quick access to some of the Pacific Northwest's most recognizable outdoor destinations, including Mount Hood, the wineries of the Columbia Gorge, and the waterfalls of the scenic area. Its position as a halfway stopover between Portland and eastern Oregon also gives it a steady flow of road-trippers, cyclists, and outdoor travelers who appreciate a comfortable base within reach of waterfalls, vineyards, and river vistas.