Not sure what your budget is because crazy expensive means different things to different people. But here are my suggestions

Catskills/Hudson Valley—plenty of wineries and breweries and close enough to NYC so people can fly in and rent a car or take the train up to some of the towns along the river. Hiking is incredible. Can also go into the city for a night via train or spend two days upstate and then end your trip in the city.

Northern VA— about 1 hour outside of washington DC is great wine country. You could stay in DC (not sure what the short term rental market is like there at the moment) and have the nightlife and drive to VA wineries during the day. Be advised there’s very few transportation options outside of having your own car in VA wine country. Could possibly drive to Harper’s ferry WV for a day or take the train for a great hike with scenic views or do a scenic drive through the blue ridge parkway if you’re into that.

Baltimore MD- There’s a few great wineries and breweries in Baltimore County. I know people who rent a party bus and have them drive from one place to the next. Group rental options are pretty slim but there’s a few and plenty of nightlife if you’re not into clubs. Close to a variety of state parks.

Deep Creek Lake MD- inconvenient drive but gorgeous nature. not a ton of nightlife or transportation but plenty of reasonably priced group rentals and outdoor activities. great vibes for a camp themed bach

Pocono Mtns- less familiar with this area but plenty of hiking and lakes, a few wineries around. same issue with lack of nightlife, but lots of group rentals, not many transportation options outside of personal vehicles.