Before you get to Crater Lake, I suggest exploring Ashland and the greater Rogue Valley.
Outside Ashland, I highly recommend spending some time in the Siskiyou Mountains. Whether you have kids or not, Willow Witt farm is a wonderful retreat. Stay the night in a lodge room or ‘glamping’ style in a canvas tent. In Ashland, I recommend Ashland Hills Hotel or the downtown Lithia Springs hotel. You can take in a Shakespeare show or just enjoy the culinary scene here.
Outside Ashland, the Rogue River is one of the most beautiful spots in the valley. See it in multiple places: head up to Shady Cove when you’re en route to Crater Lake and check out the lava tubes up by Prospect and Union Creek, or watch the whitewater rafters north of Ashland at Galice. You can even hike part of the river on the Rogue River Trail there.
If you’re into winery tours or wine tasting, check out the Applegate Wine Trail or Upper Rogue Wine Trail. Applegate Lake is a wonderful place to hike and swim (past Ruch and Jacksonville), and historic Jacksonville is charming as well!