Winchester Inn

35 South Second St., Ashland, 97520, OR

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1 Room / 2 Adults

1 rooms,
2 adults
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This historic old Victoria home in the heart of downtown is a wonderful B&B alternative to the usual hotel stay. The spacious rooms are beautifully decorated with antiques. Many of the rooms can accommodate a small family of three or four, with king and queen beds, plus twin beds or sleeper sofas. The hotel has a larger family suite in a building next door, if you need to sleep up to five people comfortably.

The family that runs the Winchester Inn obviously puts all of their love and attention into the place. That includes the on-site restaurant, Alchemy, where guests eat a free breakfast. Parents will love the quiet luxury of the inn, while older kids will be enthralled by staying in what seems like someone’s old mansion. Other amenities include jetted tub, fireplaces, air conditioning, bathrobes, free homemade cookies, and a coffee bar.

Our Editor Loves

  • Free gourmet breakfast
  • Historic Victorian home
  • Free Wi-Fi

Family Amenities

  • Family Room 5+
  • Free Breakfast
  • Free Wi-Fi
  • Onsite Dining



by AngusDad

We have been coming to the Ashland Shakespeare Festival for years and always stay at the Winchester Inn. The rooms are spacious, the beds comfortable, and there is never any deferred maintenance. It’s an easy walk to the Festival venue. The included breakfasts are gourmet.

Charming luxury!

by crosscourtforehand

Ashland is a charming town, and The Winchester Inn is a wonderful b&b - beautiful grounds and rooms, nice location, and delicious breakfast with menu options for the main course (with quantities that are not overwhelming). We enjoyed the private patio outside the door to our Patio Room. The whole place has a very luxurious feel, and there is ample staff to assist. The town is very walkable and we went to and from for shopping and later, to dinner (we enjoyed dining on the patio of the nearby Pie and Vine). You have to be a bit of a mountain goat for parking at the inn, but there are several options available. We would love to return to this inn if ever in the area in the future.