IMHO, Cleveland is a very underrated city. I say this having grown up in a much larger city. It has all the amenities of a larger city, it just doesn't have two dozen of each. The biggest downside having lived there is that public transportation is not helpful for anything other than trips to the airport (for which it works great). The city is very neighborhood-centric, each neighborhood having it's own quirks, shops, and independent restaurants. Basically everything is about 10min from everything else, but there's a ton to explore. Fortunately there's very little traffic outside of the 4-5p hour, so getting around in a car is simple (just watch out for the traffic cameras which outnumber the entire Ohio state population).
Also look at the climate, housing, cost of living vs salary, entertainment and direct flights (for vacation and fellowship interviews) in each area. A day in New York is more than doable from New Haven (two hours by train). Also there are beaches close. I can't tell you about Cleveland; I haven't visited Ohio. Does it snow enough there so that one needs winter tires, or at least AWD?
It's rather cloudy from Nov-March, and while it snows frequently, it also melts frequently, so rarely do you have more than 6in of snow on the ground at any given time, although AWD wouldn't hurt
😛 (and hasn't New England already received like 6ft of snow in winter 2015?

). Like I said above, depending upon how far you want your commute to be, you can live in dozens of different communities, none of which fit the mold of stereotypical "cookie-cutter suburbs." Many attendings live in Pepper Pike, Shaker Heights, or Lakeview, all of which can get you to the hospital in under 25min
on a bad traffic day. Most residents live closer in either Cleveland Heights or the emerging downtown district. If you know you'd be miserable if you weren't within a train ride of the 3rd most populous city in the Western hemisphere, then by all means go to New Haven. As far as the beaches, there is a fairly large pond on the northern boundary of the city.