Ashland Winery Hotels

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 storey 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 area. 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 cosy accommodation with period furnishings. The walkable streets connect easily to city centre Ashland, making exploration a breeze without the need for public transport.

Historic City centre District brings Shakespeare to life in Ashland's charming centre. The renowned Oregon Shakespeare Festival anchors the area with Tudor-style theatres surrounded by Victorian shopfronts. Lithia Park offers a peaceful escape with bubbling mineral springs, while art galleries and boutiques fill historic buildings beneath colourful 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 area. Most attractions sit within a three-block radius, making cars unnecessary for exploring this theatrical paradise.

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 area perfect for theatre enthusiasts. Accommodation range from charming bed & breakfasts in restored Victorians to boutique inns with period furnishings. City centre Ashland's diverse restaurants and artisan shops are just a 5-10 minute walk away. The neighborhood's uncrowded pavements and proximity to Lithia Park create an ideal base for exploring Ashland without a car.