How We Choose What Hotels To Stay At In Times Square (And Why We Wound Up Staying Somewhere Way More Expensive Than What We Would Usually Pay)

We had managed to acquire tickets to see Hamilton and I scored some great airfare to New York. Now it was time to decide where to stay. In this post I’ll be going over my usual procedure to find hotels around Times Square. We left on a Friday morning and returned late Sunday night. I’ll break the trip up into segments because I think each one is interesting on its own merits. I’ve listed the other posts about our very quick trip to NYC below. The one in boldface is the one I’m focusing on today.

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Why yes, I do have a Google Maps set up for all the hotels we’ve stayed at before.

When booking a hotel in Times Square, we need to make sure it meets certain criteria. Since we always seem to visit New York in the winter, Sharon insists that the hotel MUST be within short walking distance from the shows we are seeing, “because it’s too cold out to walk very far” (she’s a wimp when it comes to cold [Edit by Sharon: True story! That’s why I moved to Florida!]). Preferably we should be somewhere between 42nd and 50th and from 6th to 8th Avenues. So you see I have a lot to work with. 😉

I find New York to be one of the most frustrating hotel markets in the country to work with. Every chain hotel is usually way overpriced because everyone from all over the world knows what a Marriott or Holiday Inn is and feels safe booking a room there. However, many of the hotels in New York City are not major chains but individual properties. Picking hotels is even more difficult because places will be bought, renamed and otherwise changed to keep people from knowing where they are staying (Did you know the Row NYC hotel is actually the old Milford Plaza?).

We’ve stayed in our share of hotels in Midtown Manhattan and have developed our list of  hotels where we have stayed in the distant past, like the Casablanca Hotel (they were nicely priced when they first opened) and the Marriott Marquis (we’ve occasionally seen a good deal on it), but the prices are almost always too steep for us. We also have our go to hotels. I’ll always look to see what rates are at the Crowne Plaza Times Square Manhattan or the Distrikt Hotel. The prices there are usually competitive and we’ve had pleasant stays at both of them.

Booking a room for this trip was vexing me to no end. The Distrikt Hotel had some good rates (around $500 for 2 nights) but Sharon still isn’t thrilled about staying there as it is on 40th St and a little further than we (well, she [edit from Sharon: shut up, Joe ;-)]) like to walk in the cold. I found another hotel on my go to site for hotel reviews, TripAdvisor, which I determined would fit our needs and would only cost us around $400. Heck, we had already spent enough money on tickets for Hamilton; I didn’t want to drop a whole lot of money on a hotel. Then it happened. I saw this headline on one of the blogs I read:

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OK, Deal of the year is major clickbait to me. What is this offers to end all offers.

compnight
The offer that was so good it only lasted 24 hours before it was pulled.

Wait a minute. Does that say that when you book a stay at any Waldorf=Astoria hotel that you’ll get a night free? Everyone seemed to think so. Book one night and get the second one free. Well, I had a stay for 2 nights coming up in New York City. They have a Waldorf=Astoria there. They have THE WALDORF=ASTORIA there; the original! The grandaddy of all Waldorf=Astorias! I went to the Visa Luxury Hotel Collection website and found a room at, not only the Waldorf=Astoria, but at The Towers of the Waldorf=Astoria. This is the hotel within the hotel that consists of only the upper floors. The standard rooms here start at 600 sf (which is MASSIVE for New York). I’m interested.

Not only do you get the fancy hotel within the fancy hotel but because I’m booking through the fancy hotel website I also get:

  • Room Upgrade, subject to availability
  • Free in room internet
  • 3PM late checkout, Subject to availability (FWIW, it wasn’t available)
  • Complimentary Continental Breakfast
  • $25 food and beverage credit

I checked the rate on the website for the nights we were looking for. The total for the 2 nights after taxes came to $1000. Wow. That’s why we’d never stay there. However, with this offer we would only be paying half of that. $500 for 2 nights at the Waldorf=Astoria tower. Not counting the $25 food credit and free breakfast. Oh, I also forgot to mention the other offer which Visa had where you might get a $75 gift card REBATE after your stay. For the regular price it would be the same as the hotel we liked but was too far away. For the price after rebate, it would cost the same as the hotel we’d never seen before and had “good enough” reviews.

I took a deep breath and got ready to make my presentation to Sharon. The hotel is on 50th and Park. Way out of our usual neighborhood. I need to book this now because a deal too good to be true usually is and won’t last (as it was the deal was pulled after 24 hours). “Um, honey? How would you feel about staying at a fancy hotel? ‘Which one?,’ you ask. The Waldorf=Astoria. There’s this great deal…yeah I know, more miles and points stuff. But I need to book this now. Yeah, I think I heard something about it closing for renovations too. You’d be OK with it? Really?? Thanks!!!”

Off to book, crossing my fingers the whole time that the deal is still there. It is. Now looking at comments of other people who booked and everything looked OK. It’s a refundable reservation and we have several months until our stay. I can see if other people had problems way before we’d be going. BOOK IT ALREADY!! Done.

I hit the “reserve” button and I got my confirmation. I still kept my other two reservations for a while. I read on the message boards how other people had completed their stays and were greeted with the offer and how the last night would be free and received all the upgrades. Eventually people even got the $75 gift card. I finally cancelled my other reservations. There was no turning back now. We’re going to be staying at the Waldorf=Astoria. This is gonna be so cool! Stayed tuned for Sharon’s review of the Waldorf=Astoria…

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