We were in Ashland, OR at the beginning of the month to see some plays and managed to get in to the Winchester Inn. Managed is the operative work as one must book a room selection well in advance. This place is just that popular.
We stayed in our favorite, the Sunset room. It is well-appointed, comfortable and has a private balcony for relaxing in the morning, in the evening, or at any time one needs a break. The bed is a great old frame that, with a comfortable bedding set, raises the sleeping surface to waist level--a portable step is provided for climbing in at night. The Sunset room is accommodating, nicely decorated, and just right for size (not spacious). Other, larger rooms are available, but the prices rise sharply.
The staff is very hospitable and friendly, eager to assist the guests and always available. We felt like we were really appreciated and welcomed to the inn. Breakfast comes with the room. It is served in the dining room and the service staff acts like you are paying $35 for breakfast for two, not enjoying a complimentary breakfast. Seating is in the dining room, and the service is superb. We enjoyed the Belgian waffle, the fruit cup, the scrambled eggs, etc.--all presented very excellently.
The Winchester Inn presents a grand experience for the avid Oregon Shakespeare Festival participant.