Winchester Inn - Hotel in Ashland - 35 S 2nd St, USA

Fantastic experience top to bottom from check in to an incredible breakfast. The property is immaculately maintained with first class amenities and so many thoughtful touches like freshly ground coffee in the fridge, a bucket of ice and truffles delivered on arrival. The bed was ultra luxurious and comfortable. An extensive breakfast menu of gourmet selections was offered including juice and a starter course of fruit and a warm pastry. I then enjoyed the smoked salmon benedict. This is one of the best B&B/Inns I've enjoyed.|A bonus is The Alchemy, one of the finest restaurants in Ashland on the premises.

We enjoy staying at the Winchester Inn when we come up to Ashland. The staff are very attentive. The breakfast is excellent, with many options. The setting is very relaxing. The location is ideal. It is close to the Oregon. Shakespeare Festival and several excellent restaurants. Lithia Park is just the other side of the Festival. From the Inn it is one block down to the Main Street where one can explore many of Ashland’s unique shops.

I lucked out when I got this room! It's amazing here. So comfortable and clean. Beautifully furnished. Nice touches during your stay. Your room is made up while you're at a really delicious breakfast! And if you're going to spend time at Oregon Shakespear Festival, all plays are within about 2 blocks away. Really great location in the heart of historic downtown Ashland.

First visit to this inn and loved it! Impeccable room (Catherine M.) with everything you need. Super friendly staff. The gourmet breakfast had great options and food was superb. Highly recommend, especially due to the great location to downtown.

Breakfast is amazing! I stay at the Winchester inn every few months for business. Travis is very helpful and always makes me feel welcome!

Very grateful for the empathetic owners of this fabulous place. I had booked it thinking it was in another state when I realized I had booked the wrong place. The owners were very gracious to give me a refund. My only regret is that I didn’t actually get to stay at the place and will go out of my way to go there

We booked the two bedroom cottage with two king beds and two bathrooms plus a pill out sofa. The cottage is a separate small building off the parking lot alley. Although it doesn’t look like much from the outside the inside is a 5 star hotel. Comes with small fridge, coffee maker, microwave and all the amenities you’d expect from a top notch hotel. The area is surprisingly very quiet. No one above or near you. The best part is the complimentary breakfast which is gourmet! It begins with a scone with fruit curd and cream then you get a great selection of breakfast plates - French omelette or eggs Benedict or gravlax. Very impressive!! Easy free parking in the alley. Very knowledgeable and efficient house staff. Everyone was friendly. I would definitely stay again. We have zero complaints.

We really enjoyed our stay in the Eleanor Rose Suite. It was on the top floor of a Victorian house with dormer windows, so had lots of charming changes in the roofline. The room was large, with lots of space to move around and a sofa and comfy armchair for reading. We enjoyed looking down on the town of Ashland and the beautiful mountains beyond. ||||The location was a few minutes from the Oregon Shakespeare Festival and downtown Ashland so we walked everywhere.||||We splurged in getting this suite and part of the reason was because of the extra convenience of EV charging at a nearby sister property. Upon our arrival, we learned they no longer leased that property, so no charging included…a bit of a disappointment. But there were so many thoughtful touches, the staff was so friendly, and the breakfasts so wonderful that we thoroughly enjoyed our stay.