1

No and yes.

Third party booking sites have only a small number of rooms they can use. The hotel gives a few rooms to booking.com (for example), a few to some other site, and keep the rest for themselves.

The "only 2 rooms left" is a gimmick the sites use to encourage people to panic-book a room with the site. Possibly, their 3-4 room allotment is indeed booked up and they have nothing left to offer.

This isn't a theory I cooked up. On a recent trip, for example, I asked at three different hotels on two continents precisely these questions, and I received the same answers from all three places. Chats I've had with hotel/pension owners in some other European countries, Greece included, is consistent with this.

Do what you normally do. In September, no problems.

2

And most rooms in booking.com for example have free cancellation so people might book up to be sure and then cancel the ones they don´t want!.That´s what I did myself for apartments in Madrid for October!

Ingela

3

I agree with BthDth but i would like to add that the accommodation owners themselves decide how many rooms they put on Booking.com.
One should also be aware of the fact that hotel owners have a love hate relationship with such booking sites, in Greece even more than in other countries. Knowing that Booking.com charges a commission of 17% minimum explains enough*.

For your destinations and that time of the year i wouldn't pre-book. It doesn't hurt to write down some price quotes from the booking site and you may end up with even cheaper rates if you just walk in. Also, many of the cheaper (but sometimes excellent) rooms in Greece still have no web presence.

*I usually book for the first night(s) only (where i will be staying after my flight into the country) and nowadays i tend to contact the hotel directly which is highly appreciated.
For example, on my last arrival in Chania, Crete i had found a place on Booking.com for €48. When i contacted the hotel directly they have promptly offered me the rate of €40 through mail and i didn't have to give my cc number nor did i have to pay anything in advance.
What i have experienced with that booking has happened many times (not always) but expressing to the owner that you prefer to avoid them having to pay a steep commission is always very much appreciated and in our case it has sometimes resulted in 'something special' like an upgrade of the room, a free breakfast, or a welcome drink.

Only in big chain hotels this will not always work as the staff at the desk can't make any decisions, but i think we are not discussing such type of accommodation here.

4

Lovely advice and thank you. A fairly normal practice that works well for us is that described by artemis2 - checking sites to get a sense of accommodation style and then telephoning the hotels etc directly. With the time we have we can easily adapt our plans.

Love the suggestion regarding the owner avoiding a steep commission - I'll now add that to my repertoire