Chris - I'm a fan of The Crosby Street Hotel

The Bowery Hotel 

and the The Mercer.

My favorite restaurant at the moment is Kyo Ya. 

Close by, and a great spot to grab amazing cocktails, is Dear Irving.  

Of course, get your caffeine fix at the upstairs Blue Bottle Coffee(the Siphon Bar is open from11:00 - 3:00)

and then head over to Brooklyn to the newest Blue Bottle Coffeeon Dean Street.

I highly recommend trying the The NoMad Hotel, right around the corner from Ace Hotel New York.  

Ace can get extremely loud, which sometimes bugs me, as does the requirement to look like a lumberjack-cum-brogrammer.

NoMad is a little snootier in vibe, but the rooms are great (ensure a larger room), and my favorite aspect is the food.

Eleven Madison Park Restaurant is always booked for weeks out.  It's one of the most famous restaurants in NYC.  Unbeknownst to many, Daniel Humm (exec chef from 11 Madison) does all the food at NoMad.

I highly recommend brunch or lunch -- less crowded than dinner -- and getting the duck or slow-cooked egg.

Definitely worth a test drive.

Smooches,

Tim

The cool kids are still staying at Ace Hotel New York as far as I could tell when I was there a few weeks ago.

Since budget doesn't seem to be holding you back, I would get down to Soho and stay at the Crosby Street Hotel. Great design, nice vibe (honor bar in the lobby), central to all things soho, and the room was so quiet I slept like a baby (unlike many NYC trips).One other option I would try, and will on my next trip there, is The NoMad Hotel. Daniel Humm is associated with Nomad, and after eating at his Eleven Madison Park Restaurant on my last trip and being wowed,

I want to check out Nomad. If you stay there, let me know how it was.  

Crosby Street Hotel has good Soho location and nice vibe.  It's elegant without being stuff or pretentious.  Location is in Soho, but Crosby St isn't crazy busy.  And walking distance to PUBLIC, Balthazar Restaurant, and Prune.

Also, if I may shamelessly self-promote, forward your confirmation email to checkin@checkmate.io to use our mobile check-in service before you arrive to get a better room, avoid a wait at the front desk, etc.

I concur with Tim's recommendation of The NoMad Hotel above (restaurant does the best roast chicken in the world, has to be sampled). For serious comfort (and if budget is not an issue) I recommend the Crosby Street Hotel down in Soho. Companion hotel to the hotel I always stay in in London, the Haymarket Hotel - great rooms, great bar and restaurant, outdoor terraces, nice loft vibe: http://www.firmdalehotels.com/new-york/crosby-street-hotel

My go-tos are the Crosby Street Hotel, Bowery Hotel, Greenwich Hotel or Trump SoHo Hotel. They're chic and cool without being overly trendy. 

Lot of good recommendations already, but I'll add a couple of items:

• the Greenwich Hotel is a great spot, more mellow and laid back than some of the hipster joints mentioned in other reviews, but old school cool, New York.  Great Italian restaurant, Locanda Verde on ground floor.  Interesting fact, the hotel is owned by Robert DeNiro.
  
  
  
  
• The The Standard New York has incredible views over the Hudson to Statue of Liberty, etc., and a great bar on the top floor.  Bonus points for having the High Line Park run right through the bottom of the hotel.
  
  
  
  
• In addition to being a cool hotel, the room service at the The NoMad Hotel is insanely good.  
  
  
• I've never stayed at The James Hotel New York, however, I have drank at the rooftop pool bar and that is a nice spot.  

I would try Hudson Hotel. It's a little off the beaten path but it's cool without being too self-conscious and has a very classic yet of-the-moment vibe. It has a very Tom Ford-y kind of feel to it. 
If someone told me I could stay anywhere in New York and not have to worry about the money, I wouldn't be able to resist staying at least a night at The Mark Hotel. It's a very old school, classic New York vibe--don't expect a lot of hipsters wearing pork pie hats in the lobby, but it has a very fresh feel both literally and figuratively. Beautiful, beautiful rooms and a lot of really fun little amenities (like bikes and Laduree macarons in your room). It's the kind of place you can see a Katherine Hepburn/Spencer Tracey movie taking place. 

Hey Chris, Check out The James Hotel New York. It's right at the nexus of SoHo and Tribeca. It's a great spot with a Rooftop bar and pool. Also 60 Thompson-A Thompson Hotel or the Thompson LES (a little more E Village/LES but in your wheelhouse style wise).

Update: I just remembered: The McKittrick Hotel for your Chelsea/UMPD (Upper MeatPacking District) activities. Plus the Heath there is an incredible night.

And Bowery Hotel is my hands down favorite hotel in the city.

Tribeca Grand Hotel is surprisingly interesting. Not full of "cool" kids, but thank god, right? Downtown LES very cool but more the Lower East Side. Hôtel Americano VERY cool but more Chelsea-esque. Crosby Street Hotel (Soho) and new Mondrian SoHo are to die for. Even if cost is no object, start with Hotel Tonight at 9AM the day of your stay for amazing deals at many of the places listed above.

High Line Hotel at 10th and 18th is very hip, very creative restoration. Neighborhood around the Highline is wonderful for exploring these days. And finally, Maritime Hotel at 9th and 16th never disappoints. And this is not to mention the amazing places you could get on AirBNB at these prices, but that's another story.

Have a good one!

I really like The Standard - East Village - beautiful views of lower Manhattan and a charming little cafe for breakfast before heading out for the day.

My favorite is eating at Bohemian.  A modern Japanese restaurant (not focused on sushi), that feels more like you're eating at a chef's living room and less like you're having another sushi / roll outing at Nobu.  Getting the "secret" number is a bit tough if you're not used to this sort of thing, but a little digging and it shouldn't be too hard to get.

Obviously, in Brooklyn, more precisely Williamsburg. I like to look for AirBNB listings in this area, the apartments are often surprising or creative, like those lofts in old Industrial buildings. Plus, if you find a way to get on a rooftop, you'll envoy this incredible view of the Island of Manhattan.

My two cents ;)

On the Island, I recently tried the Howard Johnson Soho hotel, in Chinatown. Nice place, the view on the Manhattan Bridge is crazy if you ask for a room up there, nice staff...

Hi there! I live in Williamsburg, Brooklyn and If you haven't yet explored here, i would highly recommend doing so.  I would definitely stay at the Wythe Hotel.  You'll be in the heart of Williamsburg, and have amazing city views.  The restaurant Reynard in the hotel has incredible food, and one of the best burgers in the city.  

Still can't beat the Ace Hotel New York.Ferriss is a tad grumpy on it because of the occasional noisy / crowded lobby, but it's still a great mix of casual + cultural.  Adjacent restaurants are the bomb.

Dream Downtown They have a good vibe with a nice lobby bar. They have a rooftop lounge that becomes a nightclub..pretty good scene on a Tuesday/wed night, steps from the Maritime Hotel, and new Bungalow 8, now named simply No. 8 is right next door.

Depending on what time of year you're visiting. In the summer, the Meatpacking District is cool because the restaurants and clubs/bars are all near by. If you're into that, The Dream Downtown has a crazy pool party every saturday and sunday. If you want more low key cool, then 60 Thompson-A Thompson Hotel is in a nice hood. 

Williamsburg would have been the answer a year ago. Although it is getting a bit crowded these days. I'd still look for a place in Brooklyn. I like Brooklyn Heights myself. It's only one stop into Brooklyn from Manhattan, and the rates will be substantially cheaper. Go with AirBnB.

Gansevoort Hotels (Gansevoort Park in midtown and Hotel Gansevoort in Meatpacking district). Both has lovely rooftop places with pools. You'll enjoy either of them. I personally enjoy the Meatpacking district - the place that never ever sleeps as, in fact, the whole city... Try Dream Downtown close by as well.

Try The Standard New York hotel (website) in the Meatpacking district. It's pretty hip, has a rooftop bar and a nice restaurant on the first floor, both of them are very frequented. and also near the new TAO Downtown.

The High Line Hotel in West Chelsea is in a cool spot. great renovation of an old seminary. Small, quiet, but cool. It has an Intelligentsia Coffee located in the lobby. 

Have a look at Belvedere Hotel which is located in the Theatre District. Beautiful rooms, and extremely well located to all the sights and sounds of NY. We had a lovely stay there!

http://www.belvederehotelnyc.com/

I'm a fan of the Yotel New York - 10th Avenue and 42nd St. A little west, but cheap, cool bar, and relatively inexpensive. Also, if you fly in through EWR, you're five feet from the lincoln tunnel.

Hotel Gansevoort in the Meatpacking rocks!

Crosby Street Hotel may be one of my favorite hotels in the city but my judgement on cool and hip is a touch outdated.

It's quiet (which is unheard of in NY), elegantly decorated, the rooms are spacious, and it's in Soho.

Bowery Hotel - hip, quaint, but get the one bedroom or suite.  Can't go wrong.Also, in LES, I like The Thompson LES or Hotel On Rivington, the latter has got more of a scene.In Soho, I like Mercer Hotel for its hotel bar and The Mercer Kitchen downstairs, and Lure Fishbar across the street.

Nice side, Trump SoHo New York is my go to.  I hear Mondrian SoHo is pretty nice too.If you're into a super sceney scene, then check out Dream Downtown - its got two hot night clubs in it, a fun hotel bar, and adjacent to the new TAO Downtown.

The Mercer

Royalton Hotel

Soho Grand Hotel

Tribeca Grand Hotel

Morgans Hotel

The Nolitan Hotel. Bowery Hotel. Mondrian SoHo. All nice, and great areas.  

The James Hotel New York http://www.jameshotels.com/new-york has a rooftop pool and is down in the tribeca area.

I'd stay with Airbnb in a $500 apartment, since paid expenses, so I'd experience a true interesting NY experience in a really cool apartment..

Many of the hipsters stay Hotel Gansevoort. It is near The Standard New York in the hip Meatpacking District.

Hi Chris S.

I just learned about this great hotel in New York City. 

1. Affinia Gardens (website)

It is a hotel located on the Upper East Side near Central Park home of the Rockfellers, Kennedys, Roosevelts and Carnegies. The area offers high real estate, quaint restaurants, designer boutiques plus tranquility.

This hotel has spacious rooms which can be difficult to find in New York City.

Things To Do Nearby

Tony's Di Napoli  for famous New York City Pizza

Felice 64 for a drink

Central Park Central Park Zoo

United Nations Plaza

Museum of Modern Art

Solomon R. Guggenheim Museum

Upper East Side is a peaceful location for art, fashion and shopping. It is a great place to stay for one night that is active/cool/hip. Let me know if this helps.

Regards,

Janice Temple

The Skychi Travel Guide

Hudson Hotel in the Columbus Circle area & Mondrian SoHo

I would say stay at Hotel Gansevoort, you'll be in the mix, and they have a great rooftop bar.

Yikes. These suggestions are good but a little tired. TheNoMad is a good one but it's not downtown. I'd suggest The Marlton Hotel or The Ludlow Hotel New York, Sean Macpherson's newer hotels, if you are wanting '"the latest" thing :) 

Kimpton hotels never disappoint, so I'd recommend any of those.  They have a great happy hour daily from 5-6, great hospitality and nice rooms.  If you are a loyalty member you also get money to spend on the mini bar and other customized perks. 

Bushwick neighborhood in Brooklyn.