Members-only rates
4.7 / 5 Excellent

Winchester Inn

Winchester Inn
Winchester Inn – Ashland, OR
Winchester Inn – Ashland, OR
Check in 4:00 PM
Check out 11:00 AM

About Winchester Inn

Located in Ashland, a 2-minute walk from Oregon Cabaret Theatre, Winchester Inn has accommodations with a garden, free private parking, a restaurant and a bar. Among the facilities at this property are a concierge service and luggage storage space, along with free WiFi throughout the property. Certain accommodations at the property have a balcony with a mountain view. The rooms come with air conditioning, a flat-screen TV with cable channels, a fridge, a coffee machine, a shower, free toiletries and a closet. Rooms have a private bathroom with a hairdryer, while certain rooms come with a terrace and others also feature city views. At the hotel each room has a seating area. Breakfast is available, and includes à la carte, Full English/Irish and American options. You can play tennis at Winchester Inn, and the area is popular for hiking. Popular points of interest near the accommodation include Ashland Library, Oregon Shakespeare Festival and Lithia Park. Rogue Valley International-Medford Airport is 24 miles from the property.

Amenities

  • Meeting space
  • On-site dining
  • Bar / lounge
  • Concierge
  • Dry cleaning
  • Self-service laundry
  • Luggage storage
  • Family friendly
  • Smoke-free property

Reviews

4.7 / 5
Excellent 451 reviews
  • Engine customer May 2026

    Limited parking

  • Engine customer May 2026

    Beautiful property and gardens. Friendly staff. Delightful breakfast and atmosphere. Super comfortable and quiet rooms. Close walk to Shakespeare festival and fun restaurants and lounges. N/A

  • Engine customer May 2026

    We had a nice lower floor room which was pleasantly decorated. Staff was friendly and helpful. Location is good... Quiet but close enough to OSF and downtown to walk everywhere. Hearty breakfast included. Although comfortable enough, the bed mattress had a soft surface. I prefer a firmer one but it did not detract from our visit.

  • Engine customer May 2026

    Breakfast was wonderful and the location of the inn was perfect for the Shakespeare Festival and looking around Ashland. Staff were very helpful and the bar was particularly good. Would stay here again without hesitation and would recommend to our friends. Unfortunately construction was going on close to our room which produced a lot of noise. This was completely outside the control of the inn, so we discounted this inconvenience. Would stay here again

  • Engine customer May 2026

    A lovely place to land. Beautiful Victorian with a garden to relax in. The room was so comfortable (even had a window seat) and the food was great. As was each member of the staff.

  • Engine customer Apr 2026

    Fabulous breakfast and a great room. Location is right in town, can't really get a better location for the theatres and downtown restaurants. I stay here often.

  • Engine customer Apr 2026

    Beautiful inn, rooms with wonderful, thoughtful amenities and lovely garden. Great location if you are coming for the Oregon Shakespeare Festival--can leave your car and just walk to the theater. very close proximity to downtown/shopping district yet feels far away (car and foot traffic). The complimentary breakfast was excellent and nice to have a happy hour even on weekends (with superb bar menu food and reasonably priced drinks). We would definitely plan to stay here again when we come back for the Oregon Shakespeare Festival. Not much--everything was great. The only minor complaint is our room was directly below the parlor so could hear people walking due to boards squeaking but this was only an issue before dinnertime and not an issue to interfere with sleep or morning hours.

  • Engine customer Apr 2026

    Clean, quiet, spacious. Good location; great breakfast and delicious in room cookies!! That we had to leave!

  • Engine customer Apr 2026

    Location was super, hotel was lovely to look at but ur room was near a great deal of outside noise from other guests. The wash basin in the room was not helpful and the bathroom though lovely was tight. Breakfast was a real treat. Dinner at happy hour in the bar was good but service was a bit variable. Too many people for the number of staff. Food was good. Room could have been better. An elevator would have been good.

  • Engine customer Apr 2026

    Warm, cozy and super inviting! Literally can’t think of anything.

  • Engine customer Apr 2026

    Lovely establishment, made to order breakfast, easy walking to theaters.

  • Engine customer Apr 2026

    Location, location! The property is very clean, the staff are very nice. The included breakfast was amazing! Nothing

  • Engine customer Apr 2026

    Ambience, period attention to detail Torn sheet, speciality coffee machine broken

  • Engine customer Mar 2026

    Loved it! So cute!

  • Engine customer Mar 2026

    Breakfast is pretty good. Room was dingy, and had a very uncomfortable 53" bed while it was advertised as a queen. Staff was rude when we asked about this and denied the issue. They charge a very $100/night pet fee which was not listed during booking; while pet fees are common, $100 is high to the point of being predatory. They also hit us with an additional $72 fee without saying why.

  • Engine customer Mar 2026

    The location was amazing - downtown restaurants, theaters and parks are all walkable. The gardens are beautiful and the free breakfast was delicious. The staff members are all super friendly and helpful as well.

  • Engine customer Mar 2026

    Location. Parking on site. Fantastic included breakfast. Nothing not to like.

  • Engine customer Mar 2026

    Good central location. Great breakfast

  • Engine customer Mar 2026

    Grand home with lovely room and bath. Delicious 2 course breakfast. All perfect

  • Engine customer Mar 2026

    Lovely Inn with truly amazing staff and services! Alchemy restaurant is located on the property and quite good.

Frequently asked questions about Winchester Inn

Does Winchester Inn have free Wi-Fi?
Yes, Winchester Inn offers free Wi-Fi for all guests.
Does Winchester Inn offer parking?
Yes, Winchester Inn offers free parking on-site.
Does Winchester Inn have meeting spaces, conference centers, or conference rooms?
Yes. Winchester Inn offers meeting spaces for business and group use.
Does Winchester Inn have a fitness center?
Winchester Inn does not list an on-site fitness center. Some properties partner with nearby gyms — check directly with the hotel.
Where is Winchester Inn located, and how walkable is the area?
Winchester Inn is located at 35 S. 2nd St., Ashland, OR 97520. With a Walk Score of 90, the area is rated Walker's Paradise. Most daily errands can be done on foot — ideal for travelers without a car.

What's nearby

Map of points of interest near Winchester Inn
  • Southern Oregon University 1.1 mi

Why no public rates?

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