Anyone have any thoughts on a nice comfortable hotel (around $250/night) in Midtown Manhattan near Penn Station or Times Square?

There are dozens of "nice" hotels in midtown, but whether they will be $250/night depends on when you're going (both day of the week and month). Prices during the summer are generally lower. Right now there are specials on travelzoo.com for the Millenium Broadway, Grand Hyatt, the Time, the Mela, the Mansfield for $169-199/night, but some are only good for weekends. All of these are near Times Square except the Grand Hyatt which is near Grand Central, still in midtown.

The area around Penn STation is really not terribly attractive nor is it a great location for dining, but I think the nicest options near there are the Chandler, the Metro and the Affinia Manhattan. The Affinia Dumont on east 34 st. is not far from Penn station and in a much better location. www.affinia.com

Check prices on quikbook.com too which are sometimes better than the hotels' sites. The Michelangelo is a lovely hotel north of TS and is sometimes available for $200-250 on quikbook.

We stayed at the Benjamin Hotel in Midtown and it was lovely..
It is an Affinia hotel.
Best to you OldTrout!

We are most interested in the Michelangelo, which seems to be a fit for us price wise, as well as looking beautiful on its website. However...is this a hotel that you could check-in wearing shorts and a t-shirt? Hard to be dressed up when we're going to be walking around Manhattan seeing the sights...

i should add...in the middle of July!!!

Not sure where you found the rates - but for random datse in July the Michelangelo isn't shopwing much below $500. do you have reservations there already at a better rate?

And I don't reco touring New York City in shorts and tee - it isn;t Orlando - or a resort. You would be much better off in capris or a thin skirt - or even light weight trousers - but definitely with good comfy walking shoes - unless you're positive you don;t want to do a decent restaurant or theater.

As a man, I'm guessing I wouldn't look good in capris or a thin skirt. Wouldn't it be hot in July walking around New York (ie Central Park) in a pair of trousers?

I don't recommend walking around Manhattan in shorts and a tee shirt either.

Many places have dress codes.

Drawstring linen pants would look much better and be cool and comfortable. Even khakis would be an improvement.

We'll be travelling from Long Island and staying in Manhattan for the night. We'll be taking the LIRR so we wanted to pack lightly, that's why I asked about the shorts/tee. What would you suggest about packing?

...and dressing?

I suppose nice walking shorts and a NICE tee shirt would be ok if you're just going to be walking around to casual tourist places. But it's not the proper attire for a decent restaurant at night and it's not a good way to go to the theater. Summer slacks and a regular shirt or polo shirt is what you need.