Oak Street Cottages in Ashland - Hotel in Ashland - 171 Oak St, USA

We stayed in the Oak Lawn cottage for the weekend with our dog and had a fabulous time in Ashland. 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.

Great experience! We were nervous about so many beds in so few bedrooms but six adults worked just fine. Perfect location!

This place was amazing! We stayed in the "Studio" but the space was actually huge! There was a bedroom with doors that closed, a sitting area, a living room with couch and TV, and a small kitchen area with a full sized refrigerator, microwave, and coffee making machine, a full sized dining table, and a nice sized bathroom as well. Free parking. But mostly, the location is to die for! It was an easy walk to town, shops, restaurants, and the Shakespeare Festival. So, I would highly recommend this place. And Donna was a wonderful host.

The Oak Street Cottages are an easy stroll away from the theaters and downtown restaurants. We had my 76 year old mother-in-law with us and she was able to walk the couple of blocks to the theater with ease. The only thing to keep in mind is that the theaters are on a hill, so a final incline or stairs will be required. We stayed in the Oak Tower and it was very comfortable. We were also so thankful that the cleaning staff let us enter our rental early even though they were still making the beds. They were so kind and accomodating. I will stay here everytime we visit Ashland.

Nice and convenient cottage that was very spacious and a two minute walk to the theaters. Right in the heart of downtown Ashland. We came without a car and had no trouble at all. The cottage is well-equipped if you want to cook and there’s plenty of room for everyone. We will definitely come back

We very much enjoyed our stay at the Oak Street Studio (really, a one bedroom). It was spacious and comfortable. The floor plan had some quirks - for example, all of the windows are on the side of the rental that faces the public parking lot with none in the dining room/living room, kitchenette or bathroom areas. This meant that the lights had to be on in the back part of the rental when in use - even during the day. The kitchenette has a full-size refrigerator, a microwave, and a coffee maker. This worked very well for us because we mostly eat out when we're in Ashland and just needed someplace for reheating leftovers and having snacks. There's a dining table and service (dishes, glasses, flatwear, etc) for four. There's no kitchen sink, but the bathroom is off the kitchenette and has a dish rack and basin for use. The location can't be beat - just a couple of blocks to the plaza in one direction and a few blocks to the Co-op in the other. We really look forward to staying there again!

We stay every year at the Oak Street Cottages for a reason. It's within walking distance of the Shakespeare Festival which is very convenient. The place is always well kept. Plus, there's enough space for me and my family along with a kitchen so we don't have to eat out every day. This year we were in Sherwin Cottage and there were some changes to the furniture and bedding that helped modernize it a little bit. I highly recommend them.

Just spent a lovely (albeit too brief!) weekend at Oak Tower with family (son, daughter-in-law and granddaughters). It was our third stay - we keep returning because its comfortable, homey, and well-located to the Oregon Shakespeare Festival - as well as to other activities in the downtown area. The bedrooms are downstairs, and were a bit dark - and chilly, which is really the only drawback; on the other hand, its great having a place to "chill" in hot weather! The upstairs living area was lovely - very comfortable for lounging, dining (we didn't cook "in" but easily could have - the kitchen is very well equipped!) and, in the case of my nine-year-old granddaughter who called "dibs" on the daybed - sleeping. The deck was lovely as well - I managed to eat one breakfast out there but, on a longer stay, it's perfect for lounging or enjoying a relaxed glass of wine. Speaking of which, a bottle was thoughtfully provided by our hosts - as was the freshly baked bread, whose aroma permeated the house when we arrived (the wonders of breadmakers!). We will return!