Find hotels in Ashland, OR from ₩67,162

Step back in time to Ashland's Skidmore Academy Historic District, where Victorian-era buildings stand as elegant witnesses to the past. Tree-lined streets lead to ornate homes with wraparound porches and bay windows. The historic academy anchors this charming neighborhood, offering a glimpse into 19th-century architectural heritage. This peaceful residential haven sits just steps from the renowned Oregon Shakespeare Festival venues. Theater-goers appreciate the intimate local cafes with seasonal Pacific Northwest cuisine. Visitors can easily explore the district's preserved period homes while enjoying the distinctive atmosphere created by creaking wooden porches and rustling mature trees.

Ashland's Historic Downtown District combines 19th-century charm with world-class theater. The Oregon Shakespeare Festival anchors this walkable neighborhood where Tudor-style theaters stand alongside Victorian storefronts and cobblestone plazas. Art galleries, independent bookshops, and farm-to-table restaurants create a culturally rich atmosphere. Lithia Park borders the district with 93 acres of gardens and walking trails. During festival season, the streets buzz with theatergoers and performers. Most attractions sit within a three-block radius, making exploration easy without a car. Mountain views frame this intimate district where history and performing arts thrive together.

The Siskiyou-Hargadine Historic District showcases Ashland's architectural heritage through well-preserved Victorian and Craftsman homes. Tree-canopied streets and manicured gardens create a peaceful residential haven just steps from downtown. Travelers will appreciate the authentic small-town Oregon atmosphere while staying close to cultural attractions. The neighborhood sits within walking distance of the renowned Oregon Shakespeare Festival and Lithia Park. Historic bed and breakfasts offer intimate accommodations in restored Victorian homes with period furnishings. Despite its quiet residential character, downtown's diverse dining scene and artisan shops are just a short stroll away.