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Luxurious Accommodations
Winchester Inn, located just 300 metres from the Oregon Shakespeare Festival, offers elegantly appointed rooms with 600 thread count sheets, down feather bedding, and private balconies or patios. The rooms are equipped with modern amenities including flat-screen TVs and air conditioning, ensuring a comfortable stay for all guests.
Gourmet Dining Experience
Guests at Winchester Inn can indulge in a 2-course gourmet breakfast included in their stay, prepared with fresh ingredients. The on-site bar and restaurant with an outdoor patio offer a perfect setting to unwind and enjoy delicious meals. Additionally, a coffee bar is available for guests to grab a quick pick-me-up throughout the day.
Concierge Service and Convenience
The hotel provides concierge service to assist guests with any inquiries or bookings, ensuring a seamless and enjoyable stay. With free parking on-site and proximity to Southern Oregon University and Rogue Valley Airport, Winchester Inn offers convenience and accessibility for all travelers.
Book your stay at Winchester Inn now for a luxurious and memorable experience!
Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
Please inform of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation.
A deposit may be required at the property.
Free private parking is possible on site (reservation is not needed).
WiFi is available in all areas and is free of charge.
Pets are not allowed.
Children of any age are allowed.
Children up to and including 2 years old stay for free when using an available cot.
Children up to and including 8 years old stay for free when using an existing bed.
Children up to and including 8 years old stay for free when using an available extra bed.
People 9 years old and over stay for US$45 per person per night when using an available extra bed.
Any type of extra bed or child's cot/crib is upon request and needs to be confirmed by management.
Supplements are not calculated automatically in the total costs and will have to be paid for separately during your stay.
This is a top-notch property in Ashland, we've visited multiple times before. It's close to the theatres. The breakfasts are very good. The furnishings are largely in an antique style.
The breakfast, while free, is full of premium offerings that are not. You are presented every day with a strangely computed bill (with a credit for a free breakfast) to which you are asked to add a tip. I would prefer being asked to add a cumulative tip at check-out. Rooms haven't been updated in a while.
Nicely served breakfast ordered from a menu. Wait staff was excellent. Didn't expect the $5 charge for the coffee at breakfast.
Although it was not an issue for me, I would advise anyone that has mobility issues that there are stairs and hills on the property (no elevator).
Great location and staff. Comfortable room and amazing breakfast. They even left ice and a treat in the afternoon, which made a huge difference.
Charming place with wonderful staff.
So convenient and comfortable.
Rooms exceptionally well done and nice amenities.
Dinner at chateaubriand 36 disappointing.
Very slow service, uncooked food, just can't risk going back.
The English Gardens, the dining area, the rooms, the location-they were all stunning!
The property has a quaint, historic charm, yet offers up to date comforts (great bedding, nice bathroom, comfortable sitting area). Lots of nice little touches in the room, and the gardens are lovely. Our stay included a delicious breakfast with a variety of options. We were only here for one night, and I have a feeling that more nights would have made it even better, to have more time to settle in and really take advantage of what the inn has to offer. This is an ideal location for attending the Shakespeare festival -- the theaters are a five-minute walk from the inn, as is the rest of the main shopping/dining area of Ashland.
Possibly nitpicky, but there were instruction sheets and signs on practically every surface of the room -- what to touch, what to use, what not to do, etc. It was too much! Also, the honor bar in the room isn't clear enough -- we first went to put our drinks and supplies in the fridge and were happy to see cold bottled water already there. Took us a minute to find the sign with the prices. Good thing we looked around before helping ourselves!
The inn is gorgeous and incredibly well maintained. The little flourishes-like delicious hand made treats from the pastry check left at the room every day—bring it a level of luxury and refinement far above its price point. From the incredible included breakfast every morning to the fabulous happy hour bar, the vide is serene and the venues are exceptional.
Nothing at all to complain about!
Incredible location, gorgeous large comfy rooms, insanely good breakfasts
Everything great!
We stayed at the Winchester Inn for one night and thoroughly enjoyed our visit. The location is perfect—within easy walking distance of downtown Ashland, restaurants, and shops.
Our room was very comfortable and had a lovely old-world charm that gave the inn a warm and welcoming atmosphere. It was a wonderful blend of historic character and modern comfort.
We would definitely stay here again and highly recommend the Winchester Inn to anyone visiting Ashland.
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This our second stay here. We will be back. It is awesome B&B. The location is great, easy walk to the theaters. The breakfasts are very good with variety of choice.
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