Located in a charming Oregon town, just a five minute walk from the Shakespeare Festival complex, the Winchester offers a fine mix of comfortable accommodation, superior cuisine and top-line Oregon wines. Rooms are spacious, not overburdened by the twee Victoriana so common in East Coast B&Bs. Staff and owners -- all personable and helpful -- operate the Winchester as a boutique inn so there's no forced interaction with other visitors, and the restaurant attracts guests from the Inn and from without.
Rooms, of course, vary. Ours was well-maintained and comfortable but perhaps not one of the best in house.
I can't say the Winchester is the best in Ashland, because this was my first trip. Given that I'll almost certainly stay there again, that's a judgement I'm happy not to make.