Winchester Inn

The staff provides attentive, welcoming service. Guests appreciate the inviting, spacious rooms and convenient location with free parking. The breakfast is praised for its quality and accommodating dietary preferences.

This quaint little Inn is in a great location for all things Ashland. We have stayed there numerous times and enjoyed every visit. Each room is unique and it is fun to experience them all. Amenities abound, including a great little treat as you enter your room with a personalized card from the staff. The stay includes a wonderful breakfast at their on site dining area. The food is 5 star!

Ashland is known for fine B&Bs, and the Winchester is maybe the finest. It's really more of a boutique hotel, because it also has a restaurant that serves dinner and a bar. It is located in a well-kept old Victorian house and carriage house, only a few short blocks from the Oregon Shakespeare Festival theaters. We stayed in the Courtyard Suite, in the separate carriage house. It's one pretty spacious room with a sitting area. There are french doors facing on the garden, which is also a seating area for the bar. We'd been a little worried it would be noisy, but other than some ambient conversation at happy hour time, it was quite peaceful. The bed was supposedly queen size but it seemed more like a double bed. That said, the two of us slept very well. The bed is very high but a step stool is provided. (I'm 5'2" and was able to climb in without the step stool. Your mileage may vary.) The sheets were the softest, thickest, smoothest I've ever slept on. Just blissful. I wish I knew where they got them. Excellent pillows and a down comforter. Being a hot sleeper, I exchanged the down comforter for a nice cotton blanket I found in the chest under the TV. The bathroom was spacious, clean, and well-appointed. There is a huge bathtub and a decent-sized glass-enclosed shower. Nice soaps. Ordinary hotel towels. The water took a little while to get hot, but did not run out. There is a flat-screen TV with Roku. This is unusual for Ashland B&Bs that often don't have TVs. Good wi-fi too. You schedule your breakfast time the day before, so the dining room is not crowded and there's no wait. First course is pastry and a few pieces of fruit. The pastries were rich, buttery, and delicious. You can choose the second course from a broad menu: omelet, veggie frittata, eggs any style, french toast, pancakes, steel-cut oats with fresh fruit. Everything we had was freshly made with quality ingredients. A neighboring table needed gluten-free which was graciously accommodated. Each afternoon around 3:30, someone brings to your room a "treat" and a bucket of ice. We got different kinds of delicious cookies on two days, and chocolate caramels on another day. We didn't try the onsite restaurant. The staff were pleasant and friendly, but this is not the kind of B&B where your hosts chat you up. Again, more like a small hotel than a conventional B&B. The Winchester is not cheap but it is a very classy and high quality place, with a perfect location.