Don't know about Portland but for Bend, stay at the Entrada Inn off Century Drive, good rates, 5min from the venue, close to dinning & shopping, You just can't go wrong there. We stay there a couple of times a year & they are great!!!! Give them a call 541-382-4080
It sounds like you're trying to do this hotel-free, which could be hard this close to the events (many folks arranged lodging months ago). However, there's a Motel 6 about a tenth of a mile from PIR (USGP-Portland race site):
Motel 6 Portland North #4198
1125 N Schmeer Rd
I-5 N Exit #306-b, S Exit #306
Portland, OR, 97217
Phone: (503) 247-3700
FAX: (503) 247-8001
I'd say you should be prepared to pay for a motel room if you can't arrange for a homestay by the middle of October.
Perhaps you and a buddy could share costs.