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“Great Home Base for the Shakespeare Festival” 5 of 5 stars
Review of The Winchester Inn

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The Winchester Inn
35 South Second St., Ashland, OR 97520   |  
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Hotel website
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Hotel amenities
Ranked #10 of 37 Ashland B&B and Inns
maryland
Contributor
18 reviews 18 reviews
9 hotel reviews
Reviews in 12 cities Reviews in 12 cities
17 helpful votes 17 helpful votes
“Great Home Base for the Shakespeare Festival”
5 of 5 stars Reviewed September 2, 2013

Located in a charming Oregon town, just a five minute walk from the Shakespeare Festival complex, the Winchester offers a fine mix of comfortable accommodation, superior cuisine and top-line Oregon wines. Rooms are spacious, not overburdened by the twee Victoriana so common in East Coast B&Bs. Staff and owners -- all personable and helpful -- operate the Winchester as a boutique inn so there's no forced interaction with other visitors, and the restaurant attracts guests from the Inn and from without.

Rooms, of course, vary. Ours was well-maintained and comfortable but perhaps not one of the best in house.

I can't say the Winchester is the best in Ashland, because this was my first trip. Given that I'll almost certainly stay there again, that's a judgement I'm happy not to make.

  • Stayed August 2013, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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182 reviews from our community

Traveler rating
    157
    18
    2
    2
    3
See reviews for
20
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Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (36)
Date | Rating
  • English first
  • French first
  • Any
English first
Palo Alto, California
Senior Contributor
44 reviews 44 reviews
18 hotel reviews
Reviews in 27 cities Reviews in 27 cities
29 helpful votes 29 helpful votes
4 of 5 stars Reviewed August 31, 2013

This B & B is only one and a half blocks from the Oregon Shakespeare Festival theaters. The room we had was spacious with a living room and bedroom. Happily, it had a refrigerator and makings for coffee and tea. The bathroom has been updated, though the shower does not have a grab bar. With quite a few older people staying here, it would be a good addition. The bed is very comfortable with lovely linens. The other furniture, though, is a bit tired.
The turndown service was not as consistent as it should be. One night, only the bed was turned down, but nothing else was tidied.
The staff is very pleasant and helpful.
The breakfasts are visual and taste treats, with attentive service.
Though a person with a cane or walker could manage, there are stairs to the bar and restaurant and to a number of the rooms.

  • Stayed August 2013, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Portland, Oregon
Top Contributor
58 reviews 58 reviews
13 hotel reviews
Reviews in 14 cities Reviews in 14 cities
16 helpful votes 16 helpful votes
4 of 5 stars Reviewed August 14, 2013

There were a number of nice touches in the room. It is an older property, so I think they've done pretty well with it. A bit of an awkward walk to the dining room in the rain. We lucked out in being able to park near our room, but I could see that we easily could have had to walk quite a distance had we not. We ordered a cheese plate in our room. I thought it was lovely, nice cheeses.

  • Stayed April 2013, traveled as a couple
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Redding, CA
Senior Reviewer
9 reviews 9 reviews
7 hotel reviews
Reviews in 6 cities Reviews in 6 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed August 13, 2013

We stayed in the Catharine M room. Second story in the heritage bldg. The room & bath were very spacious and super clean. It had a balconly (however, it's shared with the room next door, so not private, if that matters to you). The queen bed was very comfortable and the linens were very high quality. The hotel was full, but you never heard anyone from the room. Great insulation. Very attentive, nice staff. They deliver sweets to your room in the afternoon, and also offer turn down service. The hotel bar is top notch. Say "hi" to Owen the mixologist. The included breakfast was unique and very delicious too. They truly take everything to the next level at the Winchester Inn and still maintain that friendly, unpretentious atmosphere. We've already booked our next stay!

  • Stayed August 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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Houston
Reviewer
4 reviews 4 reviews
Reviews in 3 cities Reviews in 3 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed August 12, 2013

We stayed in the Eleanor Rose suite and were very happy with our choice. Very nice room that is on the top floor, wonderful bed and large quarters. Loved the bar for early reading and late drinking and visiting. The staff was attentive to our needs and very helpful in our daily plans. Everything was within walking distance and so the car remained parked. The breakfast was fabulous with multiple choices, beautifully presented and delicious. The Alchemy was a wonderful experience and supported by a wonder staff. We loved the boutique inn feel of this property and felt part of the company and yet able to retreat to our quarters for privacy. We will stay here again.

  • Stayed August 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
San Francisco, California
Contributor
11 reviews 11 reviews
6 hotel reviews
Reviews in 7 cities Reviews in 7 cities
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed July 20, 2013

This was a wonderful stay in Ashland, Oregon and a few short blocks away from the Shakespeare Festival. Our room was wonderfully appointed; The Patio Room. It did include a flat screen TV as I understand that some rooms do not. The bed was super comfortable with soft linens. There is a wet bar, sink, and fridge in the room stocked with water, drinks, and wines. I also enjoyed the shower as it had duel heads. The breakfast (included in the stay) was WONDERFUL!! We sat in the courtyard and enjoyed coffee, fresh fruits and a wonderful take on eggs Benedict served in an artichoke base. I would recommend this inn for those attending the Shakespeare Festival. If you walk down the block, there are also various shops and it is quite charming. We had a very lovely stay and plan a return. We might check out some of the other rooms. You will also love the courtyard!

  • Stayed July 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Portland, Oregon
Reviewer
5 reviews 5 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed July 8, 2013

We have stayed here many times over the last 10years. True , warm hospitality, delicious breakfasts, great wine selections and welcoming bar, Lovely, comfortable rooms, well kept, charming gardens. Walking distance to theater. The owners really care.

  • Stayed July 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Additional Information about The Winchester Inn

Address: 35 South Second St., Ashland, OR 97520
Phone Number:
Location: United States > Oregon > Ashland
Amenities:
Bar / Lounge Beverage Selection Business Center with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Restaurant Suites
Hotel Style:
Ranked #10 of 37 B&Bs / Inns in Ashland
Price Range (Based on Average Rates): $
Number of rooms: 20
Official Description (provided by the hotel):
The Winchester Inn offers luxury accommodations, affordable excellence, the restaurant features local ingredients with global inspiration, craft cocktails and boutique wines. We are the only Wine Spectator Award Winning restaurant in Ashland as well as the only restaurant with a Certified Sommelier on staff. Top Chef of 2012 - Pamela Lanier's B&B Guide. ... more   less 
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