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 absolutely loved our stay here- in fact, we begged them for another night! The yurt is…read morebeautifully furnished and cozy. It's tucked up on a hill surrounded by trees. The deck outside was a great place to eat lunch, and the starry view from the skylight made it oh so romantic. If you are into earth friendly camping, you will enjoy this place- it has an outdoor shower and composting toliet. We loved these amenities, but some may not. :) Another note is that it can really only accomodate two. Perfect for a couple's getaway. It was just private enough, since it is a bed and breakfast type setting, the owners live in a house far enough away for you to have privacy, and close enough to be able to ask questions. They recommended an awesome hike close by, provided everything we needed to be comfortable, and were easy to communicate with prior to our trip and during. It was amazing and I can't wait to go back! VERY affordable too. Our trip to Ashland wouldn't have been half as cool if we had stayed elsewhere.

An amazing experience ---- lovely, accommodating, super friendly and more importatnly very clean!…read more We loved showering outside and using the no flush toilet. You can't beat enjoying coffee on the beautiful deck.

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.

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.

Stay here! You won't regret it…read more The setting and the hosts are wonderful. The rooms are great and comfortable. The grounds are nice and peaceful and even have a koi pond. Everything is within walking distance.

We resist the urge to so highly rate a place such as this, because it usually means we won't be…read moreable to get in again, it becomes so popular! But here goes... The innkeepers are ttruly charming folk who provide a beautiful experience with simple yet perfect accommodations. The setting couldn't be better and the location is ideal, situated almost downtown, half a block to the shops, bookstores, bars, and restaurants of the village. We rented a lovely one bedroom apartment for the most reasonable price. Best of all, walking distance to Caldera Brewery tap house! We loved doing laundry at Henry's laundromat, where we would visit the Book Wagon used bookstore next door. One has to drive to the laundromat, and the adjoining bookstore, but it's not a long drive. The location is also ideal because it's on the Northwest part of town closest to the town of Talent, where we enjoyed shopping for books, antiques, and other items.

I would have given this 5 stars but was disappointed in the communication and parking. We were told…read morewe would receive a text with information to get into our room at 3pm. I had to reach out to the number I found at almost 4 to ask what we needed to do to get in. She did apologize but if you put in your email your going to do something you should follow through not wait for your customers to call you. Jasmine room was beautiful and bed was comfy. Centrally located for walking to downtown.

I was on a 5 week road trip across country from Chicago and found myself here in October 2019. I…read morehave to say, from start to finish I had a very pleasant experience. The garden was lovely and the suite I was in was so comfortable, warm and so convenient. The unit had a kitchenette for cooking meals in, although walking to local restaurants and cafe's was easy and so close. Communication was easy and effortless, email or text. The easy in and out of the unit with a code on the door, so no keys to potentially loose! lol. The porch my unit had was a lovely place to meditate each morning. The fresh scones and coffee each morning are a lovely treat. And an opportunity to chat with others if desired. The cat on the grounds is well taken care of and, like most animals, will meow as if no-one-ever-loves-me, lmao! I had no problems with noise from neighbors or the street, (and as a seasoned traveler i pack ear plugs just in case, right?!), and parking in the back lot was a breeze. I stayed for 5 days and loved the magic and serenity of the Carlisle Garden Suites. If my travels bring me this way again I would stay here! Enjoy!

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.

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 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!