The Best Hotel in Ashland, Southern Oregon

Background Illustration for Hotels

The Oregon Shakespeare Festival has stimulated one of the most extensive networks of B&Bs in the Northwest—more than 30 in all. High season for Ashland-area bed-and-breakfasts is June–October.

The Winchester Inn

$$$ | 35 S. 2nd St., OR, 97520, USA

Rooms and suites in this upscale Victorian have character and restful charm—some have fireplaces, refrigerators, and wet bars, and private exterior entrances, and most are well suited to having one or two children in the room. Not only are the meals smashing, the location is smack-dab in the center of Ashland's hopping theater scene. The celebrated restaurant, Alchemy, relies upon locally grown produce, fresh fish and meats, including liberal use of herbs from its own garden. The breakfasts are works of art. 

Pros

  • Posh yet unpretentious
  • One of the more child-friendly B&Bs in town
  • Surrounded by lush gardens

Cons

  • Among the more expensive lodgings in town
  • Downtown location can feel a bit busy in summer
  • Some rooms are reached via steep flights of stairs
35 S. 2nd St., OR, 97520, USA
541-488–1113
Hotel Details
24 rooms
Free Breakfast

Quick Facts

Something incorrect in this review?