My husband and I stopped to stay a night in Ashland on our way home from Eugene. We love Ashland…read moreand decided to stay somewhere different than we normally do and chose Country Willows Inn and I am so glad we did! This is a stunning property. It has a huge Willow Tree in front, a pond with ducks, a gazebo with a beautiful garden area and pond with fish, and is just so well done. We watched deer in the morning while we ate our breakfast! Lisa was so nice and took good care of us! Cookies when we arrived, a handwritten note, truffles in our room. Super friendly and helpful when we arrived. Every detail was so wonderful. There is a pool also but it was closed due to the weather being too cold but I'm sure it's amazing in the summer. Parking is good also. The inn is not too far from downtown and they offer a delicious breakfast as well. We had apple cider crème brûlée and sweet potato hash with chicken apple sausage. Good coffee too! Overall we really enjoyed our stay and will definitely be back to this lovely and charming place!

I cannot say enough about the Country Willow Inn…read more Our stay there was absolutely perfect. The accommodations staff and breakfast we're 5 stars all around. We stayed at the cottage. Which has one king and and one twin bed. Perfectly appointed. The grounds are breathtaking. The pool and gardens are absolutely stunning. The cottage is situated next to a small pond with the cutest ducks quaking away., We loved it. The breakfast was off the charts delicious, fresh., perfectly made with care and love. Quiet, peaceful. You could not ask for more!

What a special place to stay while you enjoy your time in Ashland. We arrived past 5pm so we…read morechecked in by ourselves. It was a seamless experience with the keypad and our room was gorgeous. We stayed in the Captain & Lizzie McCall Suite. It is simply stunning. The king bed was wonderfully comfortable and the furniture and decor was lovely. We thoroughly enjoyed the delicious chocolate chip cookies and milk too. Breakfast was yummy too and right on time. The coffee was strong and food arrived promptly (perhaps the bacon was a little dry- but otherwise very well executed). I appreciated their communication in the days approaching our stay. Everything was seamless, comfortable, and relaxing. Exactly as we expected. highly recommend!

Our Victorian/Edwardian group, The Belles & Beaus Victorian Society of Jacksonville just had a…read morewonderful luncheon tea here. It included an exquisite frittata, the best Waldorf salad I've ever tasted, cucumber & creme cheese sandwiches, scones with clotted creme & jam, macarons, chocolate-dipped juicy strawberries, & an array of delicious loose leaf tea steeped in four different teapots. The table was set beautifully with a heavy linen tablecloth and sterling flatware. The 1883 Victorian mansion has been exquisitely restored & filled with lovely antiques. The service we received was warm and considerate. The various two pots were kept refilled with hot water and fresh water was poured for those who wished. This was so exquisite that we intend to check out their Christmas tea as well.

Sweet couple running a very clean and cute bed & breakfast…read more They have home baked cookies and delicious breakfast every morning. The rooms are pretty small and you can hear other rooms constantly but people were respectful and quite after sleeping hours so it wasn't a problem for us at all. Definitely worth the money!

Lovely Inn by charming and gracious innkeepers Anna and Brian. Every amenity provided, delicious…read morehomemade breakfast, lush garden, plush linens and bathrobes, lovely common areas. There's a reason why this inn always gets 5 star reviews and is the # 1 hotel in Ashland. Highest recommendation.

We had a great stay. The place is beautiful, we had a private entry which was so nice, and…read morebreakfast was great. I'd come again!

This is a fantastic bed-and-breakfast. The rooms are really clean, comfortable, and well outfitted…read more It is in a perfect location to walk to downtown. It is fragrance free, something that is almost impossible to find. You can find more info about that on their website. I think some of the products in the bathroom have natural fragrances, like the soap. The towels and sheets smell like no fragrance or perfume was involved in their washing. I am very sensitive to fragrances. They're very friendly and flexible about check-in. Breakfast is delicious, and they are flexible for allergen needs. I love staying here.

Everything is top notch first class here! Lovely gardens sparkling clean rooms comfy beds…read more Great people Laurie Michael and Drew do it right! Our all time fav in Ashland for pretty close to 40 years! Thank you all!

TLDR: overpriced, bad rooms and they will rip you off with hidden charges…read more The morning after checking in here, I was summoned to the front desk and very rudely informed I was being charged a $100 per night pet fee. This was not disclosed during booking, even though we specifically informed them we were traveling with a dog. While pet fees are common, $100/night is frankly predatory. My fiance and I found the bed to be uncomfortable and extremely small. The room listed a queen bed. When my fiance asked if was actually a queen, the hotel staff was rude and dismissive. We finally measured the bed with a measuring tape and found that it was a 53" full bed, not a 60" queen - very difficult for two people to sleep in. The hotel staff refused to acknowledge their error, though they did eventually move us to a vacant room with a larger bed for our last night. However, they also charged me another $72.80 for this pleasure without telling me why. At no point did they apologize or offer any other compensation or offer to waive their unreasonable fees. Beyond this, the rooms were dingy and not what I would expect at this price point. Winchester does make a good (though not amazing) breakfast, but it is not worth dealing with low quality rooms, rude staff and predatory hidden fees.

Lovely! Just lovely! Jacqui and Billy are wonderful hosts…read moreand have a beautiful home. I felt very welcome and very very well taken care of!

Every time I travel to Ashland my favorite place to stay is the Bayberry Inn. This was the first…read morebed and breakfast I'd ever stayed at in my entire life (for the first time a few years ago) and I absolutely adore it! Don't even think about staying in Medford at a chain hotel or anywhere else in Ashland because the Bayberry Inn is the nicest bed and breakfast! Now if you're not feeling social, you can pay a tiny bit extra to have your breakfast served to you on a tray in your room. As a busy Mom, who seldom travels alone, when I come to Ashland I'm alone and getting my breakfast delivered to my room is AMAZING and the epitome of the ideal relaxing vacation having someone cook a gourmet meal for me and I get to eat it alone in my room! The breakfast is truly top notch delicious! I consider myself a 'foodie' who loves to eat and if the Bayberry Inn was a restaurant I would go there just for their breakfast - it's that good! Also, like I mentioned since I'm a female traveling alone I feel sooo safe staying at the Bayberry Inn as opposed to an impersonal hotel. The Bayberry Inn is located in the North part of Ashland and it is easily walkable to everything in town or there's plenty of free parking in the town you can drive too. The rooms are clean with all the comforts of home and they have personal AC and heater too to customize the room temperature to your comfort level which I appreciated! The owners, Jacqui and Billy, are super friendly and nice! They truly care about all their guests and want you have a fantastic stay. I will continue to stay at the Bayberry Inn every time I come to Ashland - which hopefully will be soon!

This is the best place to stay in Ashland! Beautiful house, amazing breakfasts, super clean, close…read moreto downtown, kind and caring owners -- honestly one of the best places I have ever stayed in my many years of traveling.

I was lucky enough to visit briefly. Immaculate house and…read moregarden! The owners are truly great at their craft! Also their dog was so sweet

Super pretty room with double claw foot tubs. Really well appointed, could use a comfortable chair…read more No chairs in the suite. Great WiFi no tv but we brought our own little smart tv. 2 day getaway was very nice . Super flawless check in. Looking forward to staying again

We have stayed several times at the Peerless and love it each time. The rooms are all different,…read morewell appointed and quiet. We had a small issue with a stuck armoire and the owners reacted quickly and were very helpful with this small issue. You share the old Victorian with other guests but it felt very safe at all times. The downstairs has some fun history of the building, the owners are lovely and the housekeeping staff did a great job with clean rooms before checkin. Note cleaning is not provided during the stay. Coffee and tea are out downstairs as well. It's a 10 minute walk in to town, which we enjoy, so there is no need to repark the car.

I absolutely love this bed and breakfast so much. The ambiance is so charming, with such a…read moreperfectly and clearly lovingly crafted and maintained grounds and rooms. The host/owners, William and Corbet, are two of the most friendly and witty people I have met, the food is delicious, and the breakfast conversations are truly wonderful. I am already thinking of my next trip to OSF and will definitely be staying here when I do, I can't imagine staying elsewhere. It is located a pleasant 10-15 minute stroll from downtown Ashland and all it has to offer, including the Oregon Shakespeare Festival theatres.

What a wonderful place to stay in Ashland! I highly recommend booking this B&B for a unique and…read moreclassy experience. I noticed little touches that should not be missed: The sink, located outside the toilet room, had a bench you could sit on and apply your makeup ( if that applies to you). This turned a sink into a dressing table. There were also packaged makeup remover wipes... Which probably keeps their towels, washcloths, and sheets from being stained. I am very guilty of makeup covered towels in hotels...which are always white, maybe so they can bleach the hell out of them. There was a small radio turned to news. (B&Bs typically do not have TVs). And lots of lighting options. The door unlocked by code...which meant not keeping up with a key. The pool was so lovely. The garden was absolutely gorgeous. And the breakfast was very good. I can not have tomatoes or tomatoes sauces ( sadly) and they had planned a Mexican breakfast dish with salsa. Somehow, they whipped up a yummy green sauce for me instead, so last minute. ( I arrived in the evening, so not a terribly convenient time to rethink the next day's breakfast). Due to Covid, breakfast was served outside at separate tables, but we were still able to socialize. The hosts were both lovely and had a nice sense of humor. They are located very near the downtown area and we're knowledgeable and could make recommendations of restaurants. I was only there one night, but it was a perfect final stay of my fantastic 10 day vacation!

We stayed in the Oak Lawn cottage for the weekend with our dog and had a fabulous time in Ashland…read more The manager was so helpful. The cottage is well appointed, there is nothing we needed (coffee, tea, large bath towels, great bedding). Beautiful garden entry, picket fence, shaded patio with a bbq grill. Space for our pup to enjoy the outside. Within a block of downtown, restaurants, shopping, a dog park and 2 miles from the wineries. We parked our car and walked everywhere. We will definitely be back and can highly recommend for anyone visiting Ashland.

We stayed in the Studio for one night in order to catch "The Tempest" playing at the very walkable…read moreShakespeare Festival. The pictures on the website don't do this little gem justice. The space is so much more than a "studio." There's a sitting area, a small living room, a dining table, a "kitchen area" with coffee, microwave, and full sized refrigerator, plus a bathroom. The bedroom has its own doors that close, which we love because we never sleep at the same time. Anyway, this spot is amazing. And Donna treated us just like upscale Airbnb guests; always available by text. I'd stay here again in a heartbeat.