It really depends on when you are going during each of those times. Art you traveling around a holiday time? If so it will always be more expensive than during a non-holiday period, and even though memorial day isn't a huge holiday I have seen prices go up around that time. They haven't released prices for 2021 yet so it is really hard to say if the price will be a whole lot different for May vs. your already booked November trip at this point. I would hope so since that is a really high price for a moderate, I'd rather upgrade to a deluxe for that amount. Do remember that there are usually discounts too as you get closer, and POFQ has started to get some discounts so it's not impossible to get a cheaper room.
Depending on when in May you go there might be a discount. I'm staying at POR on the gift of Magic discount this May. Couldn't tell you what the nightly rate is though because I added tickets to the stay.
We booked room only for April/May 2021. Gran Destino Tower water view - $315-$329 per night (rates differ on weekends!). That was about the same rate for the same room during early May of 2020. Obviously with no discounts. So I don't think it's actually true that if you book for next year before next year's rates are available, you are charged the highest rack rate of this year.
We booked now because I have a funny feeling Gran Destino may become way more expensive next year.
And our room price won't change as long as we don't change anything - make a package, switch dates, etc. We will just buy tickets separately. And I know the price won't change because we booked room only for 2020 trip before prices came out and price did not change when 2020 rates became available. It was pretty great actually! But then we switched hotels, bunch of stuff, yadda yadda yadda - cancelled and going next year!
Not true, see my post above.
I actually had guest services call me (last year) because I kept getting conflicting information and they guaranteed me that the price that I was quoted and booked would not change regardless if new pricing was higher, UNLESS I made any changes to my reservation. And that is exactly what happened.
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