Book now or closer to September?

I would book now if you will go regardless of discounts if you are willing to pay whatever the current rate is for where you want to stay book it now and know you already have it booked and can be making payments. If you won't go without a discount then I would wait to see if/when discounts are available and book once those are out for your dates.
 
OP you didn't say what resort but POFQ is rarely included anymore. Plus with the work going on at both CBR and CSR Disney may not feel the need to offer discounts at POR either.
If you are going without the discount book now so you can get what you want.

I am planning on staying at POP.
 
There are 2 trains of thought on this subject. If you're going to go regardless of them offering FD or room discount, book now. If you absolutely have to have a discount or you're not going, then wait. As another poster said, Disney will most likely release discounts based on occupancy rates, if they release them at all. Rooms tend to go fast once the discounts are announced. Keep in mind, when Disney does announce a discount like that, they limit the number of rooms eligible for the discount. I'm going regardless so I booked my room. I'm going the last week of September and am staying at POP also. It seems like they keep cutting back the discounts and making it harder to get. Seems like I read on another thread you had to have a preferred pool view at POP to get the discount last year. I went ahead and booked a preferred room. I'm hoping for some kind of discount but, like I said, I'm going regardless.
 

I suggest you get several quotes from different travel agencies. Then, look at past historical discounts and see if any of the agencies have a deal that is better. If so, I would book. I used the 'travel agency that shall not be named' for our upcoming trip in May. We will be at POR for $165/night including tax.
 
I went ahead and booked. We are going Labor Day and staying at POP. I am using a travel agent and she will be the one to make my reservation changes once free dining is announced. I let her know what changes I am willing to make and she will take care of the rest.
 
Book NOW!!! September usually has free dining and big room discounts. I always use a travel agent when booking during Fall as most will automatically update your reservation with the discount code. Good travel agents will check the math and tell you if you get a better discount using the free dining or the room discount and adding the dining plan. Surprisingly i have had time where it was cheaper to pay for the dining plan and take the room discount. However once discounts are announced rooms fill quickly. If you have a reservation you do not need to worry about your chosen resort not being available. Exclusions tend to be the same year to year so ask the agent if the room you are looking at typically qualifies for these promotions.

When do they usually release the specials for September? I have heard around May or so.
 
If you go to the Dream about Free Dining post on the Restaurants board...there is some concern that specials will be released VERY late and Free Dining may be much more limited this year or not offered at all for fall...you'll get more info there, but if you are counting on free dining to go to Disney, you may want to check that thread out...they stay up to date with all the travel agent rumor feedback (some are more optimistic, but all seem to think bifurcated release - only early fall at first - or all later)...
 














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