Hilton HHonors - Best option for NYC using Points as Diamond - Upgrades?

Hi,

I've done a lot of reading and searching and have read a lot of what folks have said on the various NY properties. Most of the info is a bit outdated, and as we all know, hotels and services can change overnight.

My wife and I have an opportunity to have a 'honeymoon'. We never had one and it looks like December 4th-7th is our chance to have no kids and a little break.

I'm going to use my points and would like to know your opinion on the best option for us in the NYC area? I'm a Diamond and have been taken care of at a lot of properties around the country, but usually when I don't care (i.e, on business travel). I'm really looking forward to a property that has taken care of Diamonds in the past and offers us a quick way into the city (if in NJ).

I've stayed at the Doubletree at 55 & lexington, Hampton Inn times square (prefer full service for this trip), Hilton on 7th, Hilton Times Square. All were decent properties, but I can't speak about them regarding upgrades. I was not Diamond at the time.

Thank you in advance for your time and your opinion!!

Jeff

Do you want to be in Midtown or Downtown? If it's the former, I'd go for the Doubletree Guest Suites Times Square; if it's the latter, my personal choice would be Hilton Millenium. Both treat Diamonds (and often Golds) quite well.

I've stayed at many of the NY properties as Diamond using points and Diamond paying.

The only place I've been upgraded when using points has been the Doubletree on Lex. At the Waldrof, at the Millenium, at DT Suites, and the Hilton Times Square, even though I was running close to 100% upgrades when paying for a room, I got zero when using points.

Of course, everybody is different.

As for easy into the city, if you are driving there really isn't much of a difference once you get into the city to get to any of the properties.

If taking the train, there's a PATH station right across the street from the Millenium. Both the Waldrof and the Millenium have some very very nice rooms we have been upgraded to, just never on an award stay.

I would go for the DT Times Square, there you are guaranteed a suite and their regular suites are quite nice space wise.

The only place I've been upgraded when using points has been the Doubletree on Lex. At the Waldrof, at the Millenium, at DT Suites, and the Hilton Times Square, even though I was running close to 100% upgrades when paying for a room, I got zero when using points.

Of course, everybody is different.

Just to give another reference point, I've been upgraded at both Millenium and DT Guest Suites TS (in both places, to quite nice corner rooms, and given full breakfast coupons), both when staying on points. Upgrade at DT Metropolitan on Lexington (paying with points) was to a room on Executive floor, with access to the lounge. At the Waldorf (also on points), no upgrade whatsoever (fairly tiny room, that looked like it's seen its better days), but full breakfast coupons.

YMMV, as usual.

Thanks guys...

We prefer downtown, but have not ruled out jersey city or hoboken. I've never stayed at the DT timesquare - went in there once to pick up a tin of cookies for pregnant wife. Seemed nice, but obviously can't talk to the rooms.

We'll take the acela out of Boston. Less hassle than the drive. We were looking at 12/4 but may shift that to 11/27, looks like a better choice as far as availability goes.

I think the goal is breakfast in bed, a few movies, little shopping, etc, but absolutely no hard core agenda.