Now that I know that there are discounts available, I try not to pay rack rate. Last year we got the Disney Visa Discount on our room and saved a bundle. (that was at POR I think it averages about $73 a night). We also used a code that came in the mail and booked our honeymoon night at the boardwalk Inn, the rate was $220. It was a little more than what I wanted to spend, but was worth it in the fact that we had a late night at Atlantic Dance hall and it was really convenient to just walk up to our room afterwards at 1:00 am. It wasn't worth it in the fact that we didn't check in till 7:00pm that evening and didn't really take advantage of all the resort has to offer.
This September we are staying at the GF for $379 anight with AP. I normally would NEVER pay this much for a room, but this is for our first anniversary, so I am trying to justify it to myself. We stayed at a MOD the week of our wedding to keep costs down, so I feel we owe it to ourselves to splurge a little just this once. We are also spending a few nights at POP at $59 just to counteract the cost of the GF. We are the kind of people who really enjoy relaxing and spending time at the resort, so I do not think I will be dissappointed with the amount of $ I am spending to stay there. I don't want to look back and wish I would have stayed some place different.
Now on any other trip, I will not pay over $300 for a room. I would probably not pay more than $200. And again, It would depend on where it was, how much I wanted to stay there, and if it was going to be an in the parks-on the go type of trip, or a relax at the resort type of trip.