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Reviews of Winchester Inn 5 stars

35 South 2nd Street, Ashland, OR 97520, United States

#1 of 22 hotels in Ashland

Guests' Choice

Review score

Based on 378 hotel reviews

9.5

Score breakdown

  • Cleanliness

    9.6

  • Comfort

    9.6

  • Location

    9.9

  • Facilities

    9.5

  • Staff

    9.8

  • Value for money

    9.3

  • Free WiFi

    9.1

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Showing 1 – 25

  • Reviewed: 27 August 2025

    9.0
    Superb
    • Leisure trip
    • Solo traveller
    • King Room
    • Stayed 2 nights
    • Submitted via mobile

    The staff was very friendly and professional! The food was spectacular.

    Stayed in August 2025

  • Reviewed: 16 August 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • King Room with Balcony
    • Stayed 1 night

    The breakfast was absolutely fantastic! The bathroom with all the products, the lush sheets and balcony, in room coffee - all were wonderful. Thank you!

    Stayed in August 2025

  • Reviewed: 15 August 2025

    10
    We absolutely loved our stay! We will definetly return on our next trip to Ashland.
    • Leisure trip
    • Couple
    • Deluxe King Suite
    • Stayed 2 nights
    • Submitted via mobile

    Can’t think of a thing!

    The staff see to every detail. We felt as though we were living in luxury! Location was perfect and the grounds are beautiful.

    Stayed in August 2025

  • Reviewed: 12 August 2025

    9.0
    If staying in Ashland, the Winchester Inn is the only place to stay.
    • Leisure trip
    • Couple
    • King Room
    • Stayed 1 night

    We did not like our room this last time & will choose one we have stayed in before. This room was smaller & difficult to get around.

    We love this inn & have stayed there many times. The staff is wonderful & food exceptional.

    Stayed in August 2025

  • Reviewed: 10 August 2025

    10
    Perfect for theater goers.
    • Leisure trip
    • Couple
    • King Room
    • Stayed 4 nights
    • Submitted via mobile

    Central location with easy access to OSF theaters. Very comfortable room, lovely breakfast. Would stay here again.

    Stayed in August 2025

  • Reviewed: 6 August 2025

    9.0
    Beautiful and charming Victorian-style inn right in downtown Ashland.
    • Business trip
    • Solo traveller
    • Double Room with Garden View
    • Stayed 2 nights

    I received a great last minute discount from Booking.com for this room. It would have been out of my price range otherwise.

    Beautiful property, charming room, great location, tasty made-to-order (not a buffet!) breakfast. Easy and safe parking.

    Stayed in August 2025

  • Reviewed: 6 August 2025

    8.0
    Beautiful dreamy inn with beds that are just too soft
    • Leisure trip
    • Couple
    • Queen Room
    • Stayed 1 night
    • Submitted via mobile

    The bed is simply too soft and not supportive. If people traveling have any back issues and need a supportive bed this may not be the place for you. We stayed here two years ago (when my back wasn’t as bad) and I recall the bed being quite soft. This time I had to make the pull out sofa in the middle of the night to fall asleep

    The room was beautiful (bright and spacious and great location) and the breakfast is far beyond what any normal breakfast at a hotel is.

    Stayed in August 2025

  • Reviewed: 5 August 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Triple Room with Bath
    • Stayed 1 night
    • Submitted via mobile

    There was nothing to criticize. I will stay longer on my next stay.

    This was the most beautiful hotel! The owners and staff paid attention to elevate every detail.

    Stayed in August 2025

  • Reviewed: 27 July 2025

    10
    Will happily stay there again
    • Leisure trip
    • Couple
    • King Room with Balcony
    • Stayed 2 nights

    Everything was great!

    enjoyed sitting in the bar and having delicious drinks and a light dinner

    Stayed in July 2025

  • Reviewed: 27 July 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Triple Room with Bath
    • Stayed 1 night
    • Submitted via mobile

    We love to stay here. It’s close to downtown.

    Stayed in July 2025

  • Reviewed: 19 July 2025

    10
    I would recommend it for it has a lovely historic ambience with modern conveniences.
    • Leisure trip
    • Solo traveller
    • Queen Room
    • Stayed 1 night
    • Submitted via mobile

    It’s location and its setting.

    Stayed in July 2025

  • Reviewed: 13 July 2025

    9.0
    A great place for an Ashland visit. Walking distance to at least one of the theaters. In the heart of the downtown shop
    • Leisure trip
    • Couple
    • Standard Queen Room
    • Stayed 1 night
    • Submitted via mobile

    We were not there long enough to discover anything not delightful!

    The staff was very friendly getting us checked in and situated in our room. They were helpful pointing to a good restaurant as it was Monday and many restaurants are closed, including theirs. The breakfast was wonderful…made me wish we had an extra night to try their restaurant!

    Stayed in June 2025

  • Reviewed: 3 July 2025

    9.0
    We really enjoyed our stay and plan on coming again.
    • Leisure trip
    • Couple
    • Standard Queen Room
    • Stayed 1 night

    My wife has a bad hip so going up and down stairs to the room was difficult. A ground floor room would be nice.

    The breakfast was excellent and the service was exceptional.

    Stayed in July 2025

  • Reviewed: 3 July 2025

    9.0
    Comfy!
    • Leisure trip
    • Couple
    • Queen Room
    • Stayed 1 night
    • Submitted via mobile

    Stairs are steep & narrow, so ask for a ground floor room if climbing with luggage is difficult for you.

    Comfy room, friendly staff & yummy breakfast!

    Stayed in July 2025

  • Reviewed: 26 June 2025

    9.0
    Slept like a princess
    • Leisure trip
    • Solo traveller
    • Standard Queen Room
    • Stayed 1 night
    • Submitted via mobile

    Parking was challenging

    Quiet. Comfortable bed

    Stayed in June 2025

  • Reviewed: 25 June 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Comfort Triple Room with Shower
    • Stayed 1 night
    • Submitted via mobile

    Great little Bed and Breakfast We had to leave before breakfast, but the menu ( free!) looked delicious!

    Stayed in June 2025

  • Reviewed: 14 June 2025

    10
    Exceptional
    • Leisure trip
    • People with friends
    • Standard Queen Room
    • Stayed 1 night
    • Submitted via mobile

    Charming, clean, comfortable…excellent breakfast!! Great location, walking distance to everything

    Stayed in June 2025

  • Reviewed: 23 May 2025

    10
    Excellent choice for Shakespeare Theatre
    • Leisure trip
    • Couple
    • Queen Room
    • Stayed 3 nights

    bed was worn, had body indentations, upon checkout hotel said it was because of plush covering, maybe so, maybe not

    Central location, walk to Shakespeare Theatre, large comfortable room, well designed, plenty of cabinet and closet space, great shower, breakfast cooked to order was great, enjoyable dining room

    Stayed in May 2025

  • Reviewed: 23 May 2025

    10
    Next time in Ashland, Winchester Inn will be where we stay!
    • Leisure trip
    • Couple
    • Standard Queen Room
    • Stayed 1 night
    • Submitted via mobile

    Sink didn't drain properly.

    Beautiful property! Large room with comfortable bed. Excellent breakfast.

    Stayed in May 2025

  • Reviewed: 1 May 2025

    9.0
    Lovely spot in central Ashland with great breakfast.
    • Leisure trip
    • Couple
    • Standard Queen Room
    • Stayed 1 night

    Bed was way too soft: lovely to look at, but difficult to sleep in. Also a minor complaint: Inn's lawn service starting doing noisy maintenance (weed eating, etc.) right outside our window at 7am.

    Lovely property with ideal location in heart of downtown Ashland. Really excellent breakfast: choice of hot main courses cooked to order by in-house restaurant. Friendly and welcoming staff. Smallish but nicely furnished room. We stayed on a slow night (Monday; no OSF plays) and paid a very reasonable price of $160 (especially considering the breakfast); I imagine prices can get a lot higher.

    Stayed in April 2025

  • Reviewed: 19 April 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • King Room with Balcony
    • Stayed 1 night
    • Submitted via mobile

    Fantastic vintage hotel with spacious room, nice balcony and a fabulous restaurant (Alchemy) just downstairs. Will definitely stay again!

    Stayed in March 2025

  • Reviewed: 28 March 2025

    10
    great location, clean, classy, great breakfast
    • Leisure trip
    • Couple
    • Standard Queen Room
    • Stayed 1 night

    nada

    great location, clean, classy, great breakfast

    Stayed in March 2025

  • Reviewed: 25 March 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • King Room
    • Stayed 1 night
    • Submitted via mobile

    Heavy luggage up staircase

    Garden breakfast

    Stayed in February 2025

  • Reviewed: 3 March 2025

    9.0
    Beautiful!
    • Leisure trip
    • Couple
    • King Room
    • Stayed 1 night
    • Submitted via mobile

    Breakfast, service, cozy and comfortable bed. Convenient location ! Alchemy restaurant was superb.

    Stayed in March 2025

Showing 1 – 25

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