Winchester Inn

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.

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.

We stayed there and found fleas in our bed!!! We woke up with flea bites all over us. Not only was it not clean, but the people that run the Red Tail Inn are horribly rude, inconsiderate and honestly cruel. They refused to work with us on any type of accommodation and were bullying us through the whole process of the situation, telling us we were liars, and minimizing the fact there were fleas in their property. Absolutely do not waste your time or money.

We love the Winchester Inn for several reasons. The employees are friendly, caring, and professional. We’ve become friends with several of them and have remained in touch with them during these past years. The rooms are spacious and quaint at the same time. The breakfasts are always tasty and diverse. The Winchester Inn is in close proximity to the OSF theaters, nice restaurants, shopping, and coffee shops. In addition to staying here every year, we also always go to it’s restaurant (Alchemy)!!! Great food and service!!

The Winchester Inn Is so beautiful, comfortable, and luxurious! I stayed in the Belvedere room for 5 days and it was unbelievably comfortable and beautiful. The bed is ultra Lux with a soft and cozy feather bed and down comforter and the bed is triple sheeted so it felt all the more luxurious because it's all clean and fresh for each new guest and that is something special! I wish every hotel did this! It also had a jacuzzi tub with a separate shower and big soft and fluffy towels, a comfy couch, a small dining table and a window seat with a view of the beautiful courtyard. The location is the best that Ashland has to offer because it's two short blocks to Shakespeare and dead center for everything you could want in downtown Ashland. Breakfast is as excellent as everything else here with a breakfast menu that changed every single day that I was there and everything was made fresh, perfectly prepared and delicious. To say that I was impressed is an understatement. The staff here is just lovely as well and nothing seems too much trouble! They were charming and accommodating at every turn and very well informed about where to go what to do and where to eat, really impressive! If you are trying to decide where to stay in Ashland then book here because you won't regret it.

The room was charming, the food delicious and the customer service was exquisite! Easy walk to both the Oregon Shakespeare Festival and Lithia park. We stayed for 3 nights and had a really cozy rest, good bay window for reading over the twinkle lights of the garden.

We have been to Ashland many times and have always stayed at another well known hotel. This time we chose the Winchester Inn and we were very pleased with our stay. A very comfortable, spacious room with a large bathroom and an excellent on site restaurant, The Alchemy. Everyone on staff was very friendly and helpful and we really enjoyed everything about our stay. Highly recommend!