I have found most if not all places will work with you in low season for a deal, even those who are highly rated on travel sites. Better results usually if you are willing to pay cash.
One's discount will differ from another's. Loyalty is rewarded and if you make yourself a regular at a certain spot you surely will get rewarded. Also consider your on property spend as a factor. I have received free nights at a couple properties simply based on my bar tab!