Dockside Charters out of Depoe has a good reputation for producing fish. Not sure on the dates but May/June is probably good weather depending. I'd be calling them soon to book a trip dates fill up unless you go mid-week its easier to get on.
There are some good ones out of Newport also but not any I know that well.
Newport personally Yaquin Bay Charters. Went last year on a full boat of 12, caught our limit in 3 hours once we made a 30 mile trip off shore, got crab on the way back, on our way home by 1pm