It’s simple: book early cancel by 12/28/2019*
Spending NYE in NYC is an experience we all should have at least once. If NYE in the big apple is not your thing, the advice still applies. For instance you can book your NYE with points by the end of January and if your plans change you can cancel without any penalties as late as 12/28! I regret not doing that this year, some relatives were planning to come visit and since we could not take them to one of the Times Square area hotels, we did not book our stay. The relatives ended up changing their plans and heading to Punta Cana instead of cold NYC. Last year, I booked our 12/31 stay in April and also booked 12/30 about a month before. This time around, my recommendation would be to book as early as booking becomes available since this year last minute room availability is none exist! If you can’t make up your mind, you can also book 2 or 3 different locations, once you have secured your rooms you will have at least 10 months to decide where you will welcome 2020.
* Check your chosen hotel’s cancellation policy. For instance, the Marriott Marquis’s no penalty cancellation deadline is 12/10.