Have you ever heard of Mcmenamins? They are kind of an Oregon phenomenon that should definitely not remain secret. Mcmenamins has about seven or so hotels, each inhabiting an historic building. Most of them are schools converted into hotels, but the one we stayed at, The Grand Lodge, was built in 1922 as a Masonic and Eastern Star Lodge (no idea what that means either). Our hotel was 30 minutes outside of Portland and in the midst of a slew of wineries and farms, which was made for a perfect weekend getaway!
These hotels are pretty kooky...with a lot of artwork everywhere, but it totally fits Oregon. If you are looking for a clean aesthetic, this hotel is definitely not for you!
The prices are fantastic! They try to stick towards a European way of hoteling, meaning shared bathrooms but pretty affordable prices. The room we stayed in was great and only $60/ night.
Another unique feature of these hotels are the layouts. Since they are all old buildings, they tuck bars and restaurants into ever corner. During our stay, we spent the evenings trying to find new little bars (most had cozy chairs and roaring fireplaces). There is also a sweet Japanese style soaking pool that got plenty of use from us!