Here's several ideas!
The Ashland Mountain House B&B is actually the closest B&B to Callahan's. It's a splurge. Eddie and I stopped by this place last week on our way up to Callahan's, because I wanted to show him what's left of Barron, OR, just south of Ashland, which was listed on the1920 census as the home of Eddie's great great grandfather. It was just a stagecoach stop and post office. Now it's a B&B. Turns out the owner is a huge fan of my radio show, which we found out when we got out of the car, introduced ourselves, and he got excited and hugged me! It's an amazing place. Wish they did weddings. $180-$220.Ashland Springs Inn ($125-$150) This is the old Marc Anthony, smack in the middle of downtown. 7 story white building, can't miss it.
Village Suites at Ashland Hills ($125-$130) This is the old Ashland Hills Inn, at the south Ashland I-5 interchange, 8 miles from Callahan's.
The Super 8 (also at the south Ashland I-5 interchange) is $75.
The Cedarwood Inn (on Siskiyou Blvd on the south end of town) is also about $75.
The Palm Motel is across from the university & is very cute, with a pool.
The Columbia is also owned by the same people. It's right downtown on the main drag. And it's very European. Which is code for shared bathrooms, but also very cool.
The Ashland Hostel is a few blocks from the center of town right next door to my former house back in my college days, and rates range from $29 (for a bunk) to $40, $60 & $89 (they even have private rooms!). And it was featured in the book "Wild" by Cheryl Strayed!
There is also the opportunity to camp at Emigrant Lake. They have both tent and RV sites ($20-$40).And then of course, there's always the option of sleeping in your car. But you're on your own there.