Personally I would go for Late September (depending on where you're headed) - nice and quiet (but room prices don't really plummet until October) - the sea's nice and warm.
If you want deatiled info - drop me a personal message!
This applies to every standard of accomodatiom, however on the smaller islands there just is not any 3-5 star at all, it is either a small hotel 1 star or 'rooms for rent' places.
The times you suggest yourself are perfectly OK times to go.
Easy islands groups to start with would be the Cyclades, Sporades(ex Skyros), Dodecanese. You can fly direct to one of the islands within the group of islands or of course start in Athens.
There is no stigma attached to having a look at any rooms offered and then politely declining to find somehwre else.
If you arrive somehwere late just take a room for one night then look for another the next day. Most Islands have a small tourist room office and even those that don't, just ask at the ferry ticket office.
Go for it and have a lovely time.
For a first time, my start would be from Rhodes where you have a choice of Tilos, Kos and Symi. They are all a short hop from Rhodes. You'll get plenty of choice of accomodation in those places at both times of the year.
Good luck anyway.
Parky
been island hopping for years now. may/june is a nice time to go as its still low season so rooms will be cheaper. you will easily find accomadation when you arrive at a port. i think the cyclades is a good route to take.
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