The Winchester Inn

By far the best B&B we’ve ever stayed at! We stayed in the Catherine room and we so happy with everything. They thought of all the details and created such a beautiful retreat for us. Breakfast the next morning was phenomenal and the staff were beyond welcoming. The Innkeeper’s cat, Robert, made our night, too :)

We have been here three nights in The Courtyard Suite traveling with our daughter and in town visiting our other daughter and sightseeing. The room is beautiful with a queen bed and a sleeper love-​seat that they make-​up for us daily with a very comfortable air mattress.
I love the air conditioning, which is quiet and gets the room cool in a hurry. We also have a nice minibar area with a sink and fridge. A real coffee pot and fresh ground coffee are thoughtful touches too.
The grounds are lovely and we are a 5 minute walk to the plays. Breakfast is perfect and we have been able to include our daughter who is not staying here, which is very convenient.
My only negative would be in the bathroom where they jammed a huge jacuzzi tub and left room for a just tiny shower.
We would definitely stay here again.

After 30 years if having an annual Sunday Brunch here, we find that the new owners of the restaurant «doesn’t want to do that anymore»
We had 8 in our party and we are now looking for another restaurant yo celebrate the end of out trip.
4 of the people were going to book room reservations but are now staying at the Ashland Springs Hotel. It looks like they have a nice brunch
Very dissapointed.

Another wonderful stay at our very favorite place in Oregon!
We have stayed here for over 25 yrs and it just gets better !!
The rooms are all so very special .
The breakfast is the best and the wine bar is really special with the bar bites!
Friday night they had a wonderful guitar player .
We are so happy to always have Winchester Inn to look forward to!
I have a wine country retreat in Sonoma and have used Michael and Lori’s same designs to make the cottage as nice as the Winchester Inn …
Thank you Gibbs family you are all the best!

Stayed in the Barbara Howard suite, one of the most expensive rooms. It’s from the 1980s … which is likely why there are no pictures on the website, save the bed. In the website picture, there is a nice drapery behind the headboard of the bed — no such luck during our stay.
The bed, itself, is a dark green, extremely squeaky hollow metal bed. The linens are clean and comfortable. Mattress is fine, as are the feather pillows. The furniture is dated, cheap, and some (like the loveseat) are dirty and worn; the one exception is a dresser with a marble top and lovely mirrors opposite the bed — it’s beautiful and in good shape (and there is a cute, small glass vase with some fresh flowers). Carpet is a bit worn, but clean enough that I went barefoot.
The wall paint is light green … the bathroom floor tiles are teal green, with dirty-​looking dark grout. The jetted bathtub surround is banged up and has light green tiles around the top. The separate shower is 1980s pinkish and light green tile (some cracked) with dark grout). The toilet is old and the bowl seems to be stained or dirty (I thought there were sand granules in the bowl but they don’t go away upon flushing). The door to the bathroom is cheap, plastic material. An ensemble of shiny brass — from light fixtures and door knobs, to electrical plug and switch plates — are throughout.
There is a gas fireplace, about 3 feet from the aforementioned loveseat, flanked by a cheesy faux-​silk fern. There is no table in front of the loveseat — so in order to drink our champagne and eat our cheese plate, we had to take one of the end tables from beside the bed.
There is a small refrigerator with water and few other beverages (wine, beer, coffee and tea), and small coffee maker. There were also two not super fresh coconut (not French) macaroons. No other snacks in the room. Ice bucket was filled upon arrival.
The layout of the room is odd and uncomfortable to hang out in. The «front» door opens right into the side of the bed. Privacy is only garnered by closing the drapes as the bed looks over the building next door (which has the restaurant in it) and a back door which shares a landing with the room next door and the alley way (3 flights of stairs down). The bathroom is overly large and a waste of space. There are no elevators.
When they say this suite has a separate living room area, know that there is no way to close off the two rooms — so the rooms are not completely separate.
Upon check-​in, around 5:30 pm, no one was at the front desk. They were busy with dinner service and I caught the attention of someone who was very friendly and did apologize and promptly checked us in and provided someone to assist us with our luggage. There is parking in back for overnight guests. They do have turn-​down service.
The hallway carpet in this building seems new (er) and is nice. However, there are faux silk flowers throughout — just a bit tacky. The first floor entry is odd — in that there is a piece of furniture blocking what used to be a door. And, the stained glass window in the front door (to the outside) is literally about to fall out (they know about it and have been trying to find someone to fix or replace it – meanwhile there isn’t any sign (that I saw) telling guests about its precariousness).
Overall — would not stay here again; I don’t book accommodations based on «value» (it’s okay when that happens serendipitously), but I just think this place is terribly overpriced for what it is … I get that the pricing is largely for folks who come to stay for theater … however, that’s not us … we typically stop around here on our way between the Bay Area and Seattle … so it’s not a good fit for us. Still like the cabins along the river at the Weasku Inn in Grants Pass/​Rogue River City better. Were the room updated and better furnished and laid out, I’d feel better about paying almost $ 400 for the room (with taxes, etc.) — and, my husband feels the same way (which is somewhat validating, as I’m super picky … and he’s less so).
This review is not for the restaurant … I will post that review, separately.

This place is Great. Outstanding customer service. The breakfast food is amazing. I had the best valentines day ever. The owners were particularly kind and accommodating.

Best dinner we’ve had in Ashland in years. We come here annually from the SF Bay Area for many years and find most of the local restaurants to be quite ordinary and a bit over-​priced for what you get. This restaurant is special and worth the price. We shared the foie gras (which you can’t get in California) and the portion was small but delicious. The flank steak was excellent as were the side dishes and the duck was also outstanding. The apple tarte dessert was fabulous. We’ll be back next year for sure.

I’ve been here a few times with a large group. We sit in the wine cellar and get personal service. The food has always been good, but they surpassed themselves tonight. They had a special cream of mushroom soup that was heavenly. The short ribs were so tender that they felt apart and melted in my mouth. The BBQ sauce was tangy and sweet. It was complemented by sweet potatoes and blue cheese. They have a fantastic wine selection.
We arrived early and ordered a couple cocktails. I asked for a hurricane on a whim and they made one but it tasted odd. When they found out, they took it back and fixed it.

We stayed only one night, but were able to experience the delightful hospitality the Winchester Inn offers it’s guests. It’s in a perfect location just off of Main St and walkable to everything. Our room was beautifully appointed and very comfortable. The included breakfast was spectacular and the staff went out of their way to accommodate my dietary restrictions. Highly recommend.

Had a wonderful supper with my wife, son and future daughter-​in-​law. We were walk-​ins but accommodated with a table at the bar which was quite nice, not a compromise. Food throughout was fantastic, with a simple gnocchi appetizer standing out as the big surprise, but all other mains very good as well. Service was first rate with our Irish bartender. Would have merited 5 stars but the portion size of the black cod was smaller than I would give a 6 year old (all other portion sizes were normal), and the pricing is over the top even if the food /​ambience /​service was solid to excellent.

This is our second night of dining this weekend. Another good meal.
We had a lovely foie gras couple with a nice, inexpensive Limoux sparkling wine. We shared a nice butternut lettuce salad. This was a nice starry to the evening.
Rebecca ordered the ribeye; the meat was fabulous. However, her vegetables were too salty. My duck was equally fabulous. It was served with a huckleberry reduction. My vegetables were good.
We asked our server about wine choices and he admitted he could not answer our questions. He found someone very quickly who made a wonderful recommendation. We had great service.
Our only complaint is price. We had an equally good dinner last night for half the price. We will come back. However, we will go to the other place more often.

Stayed for two nights in early November and had a wonderful time. Our room had a magnificent view of the gardens… which were full of the beautiful fall foliage. The bed was amazingly comfortable and the linens were sublime. The fireplace kept us nice and cozy. The shower was huge and so was the jacuzzi tub. We enjoyed drinks at the Alchemy Bar one night and Dinner at Alchemy the second. We had such a great experience we’re thinking of making this an annual getaway!

Not only is this place an amazing place to stay, with staff that bend over backwards to make sure you have everything you need, but the food at the restaurant is amazing. The poached eggs over sourdough toast with black pepper sauce was one of the best breakfasts I have ever had. This place has to be one of the best things about Ashland. Say hi to Sarah. She’s awesome.

We’ve stayed at the Inn two times now. Our favorite B&B with regards to room choices, room quality and service. The complimentary breakfasts are one of the highlights of this excellent B&B. Creative, tasty, great texture and beautiful on the plate. Their home fries are the best anywhere. We’ve also eaten dinner here many times, as well as gotten appetizers from the same kitchen served in the bar. Easily one of the best places to eat in Ashland. Not cheap but worth it. As with the inn, we’ve never been disappointed by the food and the service is excellent.

Owen is truly an excellent alchemist. Try the Death in the Afternoon. Great experience!

We had an excellent time. Thanks to Drew and the rest of the staff. Also, prepare for a wee bit of silliness in this review.
Butter. Soft and seasoned with sea salt and parsley. Easily spread and very tasty. 5 out of 5.
Ambiance. Very posh. Beautiful jacquard table clothes, fancy push button salt shakers, comfy chairs, well apportioned seating. They moved us from of first table to one overlooking the patio and gardens of the inn. Fabulous. Best table ever. 5
Bonus point; neighbor cat in the yard and all the staff loving it. Meowser/​Robber likes to curl up in the bird bath right in front of the window and also to visit with guests. We are told he has expensive taste and often accepts handouts of scallops and fois gras from guests, and still manages to be trim.
Food. Excellent. Chef’s appetizer was a crostata mounded with crab, micro greens and candied bacon. Mini beef wellingtons: yes, please! Delicious beet and endive dish. Don’t forget dessert; espresso pot du crème with truffle and pear tart were delectable. 5
Service. Excellent. Drew got us out to the play on time. All the staff were smiling and seeming to enjoy themselves. All were very friendly and team oriented. 5
Beer list. Short but decent. Extra points for having two Russian River sours on the menu.
Might be our new favorite special dining spot.

Gayle and I had drinks here in the bar one late afternoon after an OSF performance. It was a bit rainy and grey and our window seat was a perfect place to look out, relax, and enjoy each others company. The bar was small, rustic, and comfortable. The Service from our Irish waiter was friendly and engaging, Gayle’s Bombay Sapphire Martini was made just the way she liked it, and the bar bites were tasty (especially the beer battered fries and the Mini Wellingtons. My only quibble is that beer is available in the bottle or the can only.
We dined at the Restaurant (now called Alchemy) the next evening. Gayle and I try to have one «fancy schmancy» meal during our annual Ashland trip, and our experience here was second only to the Peerless Restaurant. We ordered a bottle of Rose, and proceeded to enjoy a nice (albeit rich) sequence of appetizers, main courses (Lobster Tail and an amazing vegetarian dish), and a version of «chocolate death» (and coffee) for dessert. Yes, the meal was a little dear, but for the Oregon value, it was money well spent. We had a window seat again, and were able to linger over our food and each other as we had no play to attend. As a Date Night, it would be hard to do better than this.

— Another great place to dine in Ashland. Based on other favorable reviews, we decided to go for fine dining here, and we weren’t disappointed.
— Our experience with the service was great. Although the waitress didn’t seem to know about the Unilocal check-​in appetizer offer, she looked into it, and gave us a delicious chef’s appetizer. Definitely remember to do this; they might still be offering it, and it was a good freebie!
— Winchester Inn maintains what seem to be much lower prices on local wines, which we really liked. We were able to get a local favorite (Quady North) at a great price. I should note that Winchester is also a recipient of the Wine Spectator Award of Excellence, and from browsing their tome ‘o wine, I can see why. But — definitely go local and save.
— The entrees… great to excellent. Wifey ordered the filet mignon and I ordered the rack of lamb. We were very happy with both, but would recommend the filet. We are usually advocates for ribeye, but in this case the preparation for the filet described on the menu was too hard to resist, and the results delivered. They also mentioned that they do some sort of immersion technique on the filet that is unique.
— Overall, we were extremely happy with yet another fantastic Ashland restaurant find. I am sure we’ll be back and will be salivating until then. I am close to 5-​stars, but save that for my elite super-​echelon of all-​time mega-​greats. Maybe next time, it’ll get there, but not just yet…

Had a wonderful dinner in the very cozy bar. We started with corn chowder and roasted beet with duck breast salad and finished with a trio of yummy sliders and mini beef Wellingtons. Topped it all off with a deconstructed lemon meringue pie. Friendly bartender also made a great recommendation on a lovely white wine. We will definitely go back again.

Just wanted to offer a quick update: my sweetie and I went back for dinner here two months back and I never got around to writing about our fabulous time here.
First and foremost, the two Drews who work as waiters here are awesome. We had «dark» Drew, the brunette, this past visit, although I’ve had light (blonde) Drew before. They are not only best friends, but they are both truly fantastic waiters who offer impeccable, memorable service, perfect wine recommendations, and fun banter. We very much enjoyed chatting with dark Drew about where he likes to eat locally. He’s a very cool, intelligent guy and I respect his food/​wine opinions and really liked having him as our waiter.
How was the food? Stinkin’ amazing, what did you think?! Winchester is still my favorite upscale dining destination in the valley. My bf, who is a veggie, had the most incredible, fluffy, pillowy gnocchi that either of us has ever had the fortune of devouring. WOW. These can’t be ignored! The chef then whipped up a vegetarian entrée just for him and my bf absolutely loved it.
I had the Duck Confit and Humboldt Fog stuffed Endive leaves with honey thyme glazed walnuts and pickled radish appetizer and boy did I savor every last bite. Fantastic.
We both adored the sweet potato and marshmallow soup– how creative is that? It was divine.
For my entrée, I got the pork chop with mustard greens and French triple cream brie mac n’ cheese. It was delicious, especially that mac n cheese. Yum!
Winchester has an extensive, intimidating wine list. Don’t be afraid to ask your waiter for a recommended pairing– they know their stuff and will steer you in the right direction and will take your price range into consideration.
Overall, this was a wonderful dinner out in Ashland. This is THE place to go around here for a special occasion. Yes, it’s pricey, but it’s worth it. You won’t be disappointed, and you will enjoy the two Drews as much as we do– we ran into them both at Taste of Ashland and I felt compelled to give them props here because they are both so deserving and my bf and I were so happy to see them again, that’s how cool they both are. So go eat here, give them nice tips, and enjoy a spectacular meal in an intimate, quaint little eatery.