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.

place is fantastic, nary a complaint... recommend Room 2, the sleeping porch............read 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!

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.

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.

Also immeasurably wonderful is the service!!! Our brunch waitperson Monica always delivers the…read morejuices of choice and then comes the extraordinary cuisine. Each brunch a delightful experience in the most beautiful setting and scenery:-) Even the creative folding of the beautiful linen napkins and the creative, playful salt & pepper shakers on each table. The coffee/tea service is just the beginning of the day w/ huge, warm Buttermilk Biscuits or Scones! Happy to be home safely, but missing this fine Inn.

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!

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

Lovely, Lovely establishment. Comfortable beds. Fantastic kitchenette. Peaceful surroundings…read more Gorgeous bathroom. Great Wifi. And wine glasses?!? Who does that? Incredible staff: helpful, kind, responsive. Linda, the GM, is on top of things. Front desk gentleman (Mason?) is top notch. Mere steps from Southern Oregon University. If you haven't stayed at The Palm yet.....I forgive you. But please do better! (For your own sake). I will certainly be back here again. The ambience is just what you'd want.

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.