Iceland Trip - Help Needed

Where have you looked? Booking.com? Bungalo.com? Also, you can try zooming in on Google Maps until a "bed" icon appears, then click on that. That's how we found guesthouses that weren't listed anywhere else.

You are encountering what is becoming more and more the norm, especially for Iceland. Outside of the three real cities, there is not much in the way of lodging choices. Some of your listed activities can be done as day trips from Reykjavik, but then you have the problem of backtracking as you go back and forth.

Have you considered a camper van and sleeping at campgrounds?

Yees, that sounds normal for that time of year. Things have changed so much in Iceland even just over the last couple of years. Tourism numbers have gone through the roof. The camper van suggestion is good. You could do a ring road that way, or you could focus on the Westfjords. Another option would be to push this out to next year and book things for that time frame now.

Another suggestion would be to buy or rent camping equipment and just camp for the nights where lodging is hard to come by. I don't know I would completely change your whole trip just for this. We did 3 weeks by campervan last summer and loved the flexibility- were also glad we did the whole ring.