My family (including 4 kids) and my parents rented the Cottage and the Garden studio for several…read moredays. We had a blast. The owner is friendly and always accommodating. The sitting on horses, feeding chickens and trampoline were big hits with the little kids. The location of the ranch is just south of town, but still very accessible to Ashland and Medford (and the winery next door!). The owner was great about cleaning the grill for us and responded quickly when we had an issue or a question. All and all, a great trip, and beautiful ranch.

Beautiful country ranch with warm and gracious hosts. The ground floor apartment slept the three of…read moreus very comfortably. It even got chilly at night and the little electric fireplace warmed us right up. Just minutes from town and sooo beautiful, peaceful and quiet. The stove, microwave, and fridge were a great bonus. Would highly recommend it. Debbie and Jeff are amazing!

We have been coming to Ashland every summer since 2012 to take in a play & enjoy the city. This is…read moreour first stay at the Wesinger cottage is our new favorite.My daughter and I stayed here for 2 nights and wished that we had booked one more. The cottage is cozy, elegant and private. We appreciated the attention to details: from a comfortable bed with high quality linens, organic ground coffee, welcome bottle of Wesinger wine, local cheese + crackers, helpful notes explaining how to operate gas stove, hot tub & TV/Roku, to the night lights set up so you can find your way to the bathroom at night . You are less than 10 minutes from Ashland's downtown core, yet the cottage feels like a rural oasis, surrounded by acres of vineyard with a view of the Ashland hills. Welcoming staff online and in person at the tasting room. If you need a pool to cool down, use the city pool or Emigrant Lake day use county park, both are a 5 minute drive from tbe cottage.

Such a wonderful experience! Cozy atmosphere, friendly staff, and great award winning wines. Thank…read moreyou Marcie for being so accommodating, it was a great tasting!

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.

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.

We stayed in the High Street Cottage, #358, with another couple. They had the queen bed and we…read moretook twin platform beds in what may at one time have been the back porch but is now fully enclosed. It's very quiet and everyone slept well. The facility and its garden are impeccably maintained, part of a compound of houses, rooms and a lovely private deck with a koi pond. We were the only guests for the week, a couple weeks before the Festival began.

The columnist Herb Caen wrote of the San Franciscan native who died and went to Heaven. Saint…read morePeter met him at the Pearly Gates and gave him a tour of his new eternal home. When they finished, Saint Peter asked, "Well, what do you think?" "Nice, but it ain't San Francisco." For fifteen years, we have stayed at vacation rental homes throughout the west and overseas. We have had no bad experiences. All our hosts have been friendly and helpful. All the homes have been pleasant and homey. And our judgment never varies. "Nice, but it ain't the High Street Cottage." Each year, we arrive at the cottage to find something new. Understated and subtle, or major. Landscaping, interior upgrades, porches. Always changing yet never changing. The comfort of the familiar. We walk through the door and we're home. Back at our cozy High Street Cottage, with Mark and Elizabeth.

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!

Quiet. Secure. Incredibly comfy bed, pillows, and bedding. Bathroom completely remodeled and…read moreamazing.

This place is so beautiful and very cozy! Thankfully they also have rooms for dog owners, as we had…read moreour sweet dog with us as well. The rooms are well equipped and very comfortable! The front desk manager was very helpful & welcoming. I would definitely stay here again :)

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.

Had a lovely stay here at the Ashland Commons. The hostel was incredibly clean and welcoming and…read morewell-decorated: feels like a real home, not some anonymous hotel. Nice bathroom with shower, big kitchen and common area, lots of room to hang out. During my stay there was a minor crisis involving another guest but the staff and owner handled it very promptly and graciously. Would be happy to stay here again next time I visit Ashland!

The people who work at the hostel trade work and cleaning to stay. Do NOT give them your debit card…read moreor personal information ! Pay CASH only! I am a seasonal Firefighter /EMT and have stayed at the Commons since 2023 , never a problem and a great cheap place to stay. They have a new person named Tracey working there who has ran my debit card , that I know of, at least 2 times unauthorized last week. The first time she said she forgot to add service charges and the second time 15 minutes after my checkout time .I have been working nights this time at the local hospital, and it was very difficult to sleep there during the day with all the noise staff makes during the day. I payed on my card and extended for another day even though I was getting no sleep there and my checkout was at 1 pm , and Tracy called me at 1:15 and was upset and for the 2nd time had said she ran my card unauthorized. It did not go through so I needed to leave promptly , that I did. Tracy seemed to want to argue with me regarding their " house rules " and the cleaning. She is very aggressive and bullish and lacks respect for people. I got a text message , acting on behalf of management she claimed, that I was banned, and I still owed for a night stay ? I thought well maybe extra for a late checkout but a whole night for like 15 more minutes of sleep.I am assuming that she will continue and keep running my card unauthorized. This is why she said I was banned , and staff safety. BE CAREFUL AROUND THESE people.