Thomsons are the main operator who do this.
The hotel I have just returned from was full according to Thomson and First choice but Hays managed to get me a holiday.
Last November I booked a hotel to go this May.
This is not something I normally do but as there were not as many flights from our airport I decided to book early.
I checked the price every week and they were showing the message 1 room left or 2 rooms left right until a week before we departed.
I was happy with the price I paid and it came down £50 with Thomas cook but I was happy flying with Thomson.

I don't really know the answer to your question, but I have seen this myself. Personally, if I want to holiday in a specific month, and I see a price that I'm happy to pay, then I book it. If it comes down later on, then so be it, I was happy to pay it in the 1st place. I would hate to hang on and then find that what I wanted was no longer available.

Thomson/TUI group also do this on their airline sites, you see "2 seats left at this price" - it's a ploy to liven up bookings. Nothing to say they won't reduce the price later - although you can't bet on it.

I think Thomson do this all there time on their web-site. Goodness knows why as you can keep checking the holiday over a period of months and they will say 'only two rooms left'. It's quite insulting to the travelling public really and kind of smacks of sharp practice.

Yes, I like to browse destinations and hotels etc., but I have no intention of booking until hub and I have got the time off work confirmed, not to mention the money for the holiday..........
Mind you, some of the ones I've saved in my "shortlist" for early next year do say they're sold out now