Accomm in San Sebastian, Leon and Santiago de Compostela

I'm living in Leon right now so I can just try to give you some advice there. The majority of the tourism in Leon comes from people on the pilgrimage, the "Camino de Santiago," and in October I think the only fellow travellers you're likely to meet are these, also on their way to Santiago de Compostela (but usually on foot or by bike).
They usually stay in low-cost accommodation offered especially to people doing the pilgrimage. In October there will be a lot less demand so if you're not planning to be a pilgrim, this accommodation should still be available to you, but I'm not sure if it's available with individual rooms.

Never the less, every tourist visits the cathedral, and the plaza in front of it always has people sitting on the benches or going in and out of the tourist office, so even if you don't meet people in your accomm, you should have the opportunity at the tourist office. When I came here for a few days last Summer I stayed in a hostel in the centre called Hostal Alvarez and I thought it was nice and secure. The owner was very nice and helpful too, and you might get the price (around 25-30€) down if you ask. The phone number is (0034)987072520

Great choice going to the North of Spain, there are lots of interesting things to see here; let me know if I can help with anything to do with leon, i think i'll be here until mid-august

By the way, I disagree with your "friendly, helpful staff being pretty much a given in Spain" comment because (and i'm sure there are many exceptions) having lived in spain for a year now, my friends and I find it very offputting how uninterested & unwilling to serve the customer (chatting for ages on the phone or with other staff members) the staff are in general here.

Hi,
Just joined today ! I am looking for accomodation advice for Leon and Madrid, mid range price. My girlfriend and I will be spending five nights in Leon and two nights in Madrid in early September, any info re hotels etc gratefully accepted.