Hotels in Ashland
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Prospero's Flagship Inn
Prospero's Flagship Inn
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
Stratford Inn
Stratford Inn
Plaza Inn & Suites at Ashland Creek
Plaza Inn & Suites at Ashland Creek
Best Western Windsor Inn
Best Western Windsor Inn
The Bard's Inn, BW Signature Collection by Best Western
The Bard's Inn, BW Signature Collection by Best Western
Compass by Margaritaville in Medford
Compass by Margaritaville in Medford
Timbers INN and Suites
Timbers INN and Suites
Ashland Springs Hotel
Ashland Springs Hotel
Rogue Regency Inn Medford Airport
Rogue Regency Inn Medford Airport
Lithia Springs Resort
Lithia Springs Resort
Comfort Inn & Suites Ashland
Comfort Inn & Suites Ashland
McCall House Boutique Inn
McCall House Boutique Inn
Winchester Inn
Winchester Inn
Holiday Inn Express & Suites Ashland by IHG
Holiday Inn Express & Suites Ashland by IHG
Palm Cottages
Palm Cottages
Arden Forest Inn
Arden Forest Inn
Abigail’s Bed & Breakfast Inn
Abigail’s Bed & Breakfast Inn
Country Willows Inn and Estate
Country Willows Inn and Estate
The Peerless Hotel by WanderLodges
The Peerless Hotel by WanderLodgesGet last-minute hotel deals in Ashland and save more
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Go beyond your typical stay in Ashland
Top neighborhoods in Ashland
- Historic Railroad District
- Skidmore Academy Historic District
- Historic Downtown District
- Siskiyou-Hargadine Historic District
Historic Railroad District
Ashland's Historic Railroad District captures Oregon's cultural heart with Victorian charm and artistic soul. Tree-lined streets connect 19th-century buildings where theater and history share the spotlight. The Shakespeare Festival brings brick walkways alive with theatrical buzz. Art galleries in former rail buildings showcase local talent amid cobblestone plazas adorned with bronze sculptures. Farm-to-table restaurants serve Pacific Northwest cuisine in converted Victorian spaces, perfect for dining with regional wines. Boutique inns and historic bed & breakfasts offer intimate stays with period furnishings and modern comforts. The pedestrian-friendly design makes exploring a joy, with attractions within an easy stroll through this walkable cultural haven.
Skidmore Academy Historic District
Step back in time as you stroll the tree-lined streets of Skidmore Academy Historic District, where Victorian architecture meets theatrical flair. Ornate 19th-century buildings, including the original Skidmore Academy, tell the story of Ashland's rich heritage. The district sits conveniently close to Oregon Shakespeare Festival venues, where world-class performances bring creative energy to this peaceful neighborhood. Intimate cafes and bistros cater to theater-goers with pre-show dining featuring seasonal Pacific Northwest ingredients. Charming bed-and-breakfasts in converted Victorian homes offer cozy accommodations with period furnishings. The walkable streets connect easily to downtown Ashland, making exploration a breeze without the need for public transportation.
Historic Downtown District
Historic Downtown District brings Shakespeare to life in Ashland's charming center. The renowned Oregon Shakespeare Festival anchors the neighborhood with Tudor-style theaters surrounded by Victorian storefronts. Lithia Park offers a peaceful escape with bubbling mineral springs, while art galleries and boutiques fill historic buildings beneath colorful awnings. Farm-to-table restaurants showcase local Oregon wines, though reservations are essential during festival season. Accommodation options include Victorian bed & breakfasts and boutique inns within this highly walkable neighborhood. Most attractions sit within a three-block radius, making cars unnecessary for exploring this theatrical paradise.
Siskiyou-Hargadine Historic District
Siskiyou-Hargadine Historic District offers a step back in time with pristine Victorian and Craftsman homes lining tree-canopied streets. Take a leisurely stroll through architectural history while enjoying the peaceful vibe just steps from Ashland's cultural buzz. The Oregon Shakespeare Festival and Oregon Cabaret Theatre are an easy walk away, making this neighborhood perfect for theater enthusiasts. Accommodations range from charming bed & breakfasts in restored Victorians to boutique inns with period furnishings. Downtown Ashland's diverse restaurants and artisan shops are just a 5-10 minute walk away. The neighborhood's uncrowded sidewalks and proximity to Lithia Park create an ideal base for exploring Ashland without a car.
Learn more about Ashland
Between Shakespeare and the sublime, this artsy enclave captivates with its cultural punch far beyond its size. The Oregon Shakespeare Festival transforms three theaters into worlds of drama nearly year-round, drawing theater lovers who linger after standing ovations. Main Street's independent boutiques and farm-to-table restaurants showcase local creativity without pretension. Lithia Park unfolds like a living painting—creek-side paths wind through 93 acres where picnickers claim spots beneath ancient trees. Southern Oregon University adds youthful energy to this intellectual haven. After hiking nearby trails, soak tired muscles in Lithia Plaza's mineral-rich fountains (warning: the water tastes terrible). For a perfect day, catch a matinee, browse gallery-quality crafts, then toast the sunset with local wines.
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