If I was staycating in NYC, I'd be tempted to book at the bougie hotels along Wythe Ave in North Williamsburg (unless you live there, of course). $350 is definitely possible over less-than-peak periods, even at the Wythe Hotel, The Williamsburg Hotel or the The William Vale You'll be in a different neighborhood that always feels like a different treat from Manhattan. Obviously, once you're in Billyburg, you can just walk to your steak rez at Peter Luger Steak House (ribeye for the win). Even though it is in every tour guide, they've never done us wrong. We also have a die-hard Wolfgang's Steakhouse (founded by a former headwaiter of Luger's) fan in our group , so that would make up our 1-2 punch for steak.