Well, the obvious answer is "Der...yes" but we're on Skye for a few days and then may do ToC weather dependent. Are B&B's limited or anyone just winged it and kept lucky?
The [i]real[/i] answer is no, you do it in one day 😉
Or, if not, the answer is... depends.
More usefully, there are quite a few hostels around and will be likely to find you space, especially if riding midweek. My advice would be to google a load of numbers and give them a ring on the morning if you decide to give it a go.
If you do it in the Scottish school summer holidays (earlier than England's) then booking might be essential. I tented it on approved campsites in their summer hols and had trouble getting a pitch at Blair Atholl and in the Spey Valley nr Aviemore. Wild Camping would have been no probs obviously.
Cannot harm to phone a few venues and sound them out.