How to Get a Spectacular Hotel Room Upgrade for Free

This Approach Has Worked for Me 9 out of 9 Times

The weekend before last, my wife and I stayed 2 nights at the historic Hotel Del Coronado, just south of San Diego, CA. Using Hilton points, I booked a free stay for us in a standard room, which sells for around $350/night. I wasn’t excited about the room. It wasn’t on the ocean, didn’t have a view, etc. But we were upgraded for free to an Oceanfront Tower Resort Suite on the top floor of the hotel. That room sells for over $1,500/night. It was 900 sq. ft. large. And it had the two features that I wanted: a spectacular ocean view and a balcony to enjoy it from.

View from the balcony of our hotel room upgrade

The view from our upgraded room’s balcony at Hotel Del Coronado

The upgrade was a gratuitous gift from the hotel. That said, I took certain steps to ask for the gift. I’ve now taken those steps to try to secure an upgrade on 9 separate occasions in three different countries. In all 9 cases, I succeeded in receiving a free room upgrade. Some of the upgrades, such as the one my wife and I just received, have been jaw-dropping. Others have been more modest, but still extremely meaningful to me, providing larger rooms, connecting rooms, better views, etc. Each upgrade has added substantial value to my family’s trip without costing a penny.

In all 9 cases, I booked the rooms for free using points prior to asking for, and receiving, an upgrade. Most people might be hesitant to ask for an upgrade on a paid stay and would be downright embarrassed to ask for an upgrade on a free room. But I have no shame in asking. And neither should you. Worst the hotels can say is “no.” But that’s not what they say.

Here’s how to get hotel room upgrades—sometimes incredible ones—for free:

Step 1: Get the Name of the General Manager.

When you book a room, sometimes the confirmation email provides the name of the general manager of the hotel. If it doesn’t, a simple Google search for the name of the hotel and “general manger” should do the trick. You can also search for the hotel on TripAdvisor and then search within the recent reviews of that hotel for “general manager” or “manager.”

Celebrating my daughter Elizabeth’s 2nd birthday in style: McDonald’s lunch—true style!—and the most spectacular free room upgrade I’ve ever received: a huge suite on a high floor of the Sheraton Waikiki Hotel, overlooking Waikiki Beach and Diamond Head volcano in Honolulu, HI

Step 2: Get the General Manager’s Email Address.

Sometimes you can find the general manager’s email address by searching on TripAdvisor as described in the previous step. Another option is to call the hotel and ask for it.

When those methods don’t work, a last resort is to do what I did in the case of Hotel Del Coronado. On the hotel’s website, I found the email address for someone else who worked there, the concierge. His email address was in the format firstname.lastname@hoteldel.com. I then replaced his first and last name with the general manager’s first and last name, which ended up being the correct guess for the general manager’s email address.

free room upgrade at the Westin Denver International Airport

Staying at the Westin Denver International Airport the night before a morning flight to Mexico; I’m not sure how we would have fit were it not for the free room upgrade to a junior suite!

Step 3: Email the General Manager and Ask for the Upgrade.

Based on my experience trying different approaches, emailing the general manager directly to ask for an upgrade is the key to getting a great hotel room upgrade. I think it’s because the general manager has the power to make the upgrade happen. Unlike other hotel employees who might have to consult a supervisor, the general manager can unilaterally say “yes.” And when he or she does, it’s done.

It also seems, from the replies I’ve received from general managers, that they are happy to provide the upgrade. It’s almost as if a person who has excelled in the field of hospitality so much as to be made a general manager enjoys helping guests have a great experience. Imagine that!

What to Say in the Email

Now what you say in the email is important. The best thing you can do is grab a copy of the exact emails I’ve sent that have resulted in upgrades. You can then replace the details from my emails with the details for your trip. You can get copies of several of those emails here:

{{Privy:Embed campaign=331644}}

Looking over the 9 emails I’ve sent that have all led to upgrades, I recommend these elements that are common to most of my emails and generally appear in the following order:

  1. Set a positive tone.

    Start by expressing how much you are looking forward to staying at the hotel. Keep the email positive throughout. I’d guess that a lot of guest emails that cross a general manager’s desk are complaints. We want to set a completely different tone.

    Think about it. Who do you like to help in life? Complainers or people who are grateful, excited, and happy?

  1. Include something you are celebrating.

    Whenever possible, tie your trip to something you are celebrating: an anniversary, a birthday, a new job—something. The two best upgrades I’ve received have been in response to emails I’ve sent involving the celebration of my wife’s and my 5th and 10th wedding anniversaries.

  1. Mention TripAdvisor.

    This is an optional element, but in a couple of emails, I wrote, “I saw on TripAdvisor that you are the general manager of the hotel.” By including a reference to TripAdvisor, you’re subtly suggesting that you might leave a positive review following your stay. And who doesn’t appreciate a positive review?

  1. Include your confirmation number and dates.

    You want to make it as easy as possible for the manager to say yes to your request. Including your confirmation number and check-in/check-out dates allows the manager (or a member of his or her team) to quickly assess whether the hotel has the inventory to accommodate your request.

  2. Mention any status you have.

    For 1 of my 9 requests, I held top-tier status with the hotel. For 7 of them, I held mid-tier status. And for 1 of them, I had no status.

    Status helps, but it isn’t the be-all and end-all of upgrades. In response to one request in which I had mid-tier status, someone from the hotel told me that my mid-tier status didn’t entitle me to an ocean view, and would I like to pay extra for it? I politely declined and was given the ocean view anyway.

    If you don’t have status, I’d actually come right out and acknowledge that. I’d say something like, “Given that I don’t have status with Hilton [or whatever], I know I’m by no means entitled to an upgrade. But it would mean an awful lot to me, and if you could provide an upgrade, I’d be extremely grateful.”

  3. Ask for the upgrade.

    Asking for the upgrade you want is, of course, the most important part.

    I wouldn’t ask for 10 different things. If you know what is most important to you, just ask for that. For my most recent upgrade, I asked for “a room with an ocean view and a balcony.” That is all I wanted. Given that my wife and I were sans kiddos, I didn’t care if the room were big or small. I didn’t need a bottle of champagne or a $100 hotel restaurant credit (which, incidentally, they provided—so thoughtful—and I did not turn down 🙂 ).

    If you aren’t sure what type of upgrade you’d most prefer, I suggest pulling up the hotel on TripAdvisor and then searching the “Room Tips” for that hotel. You will quickly see what types of rooms other guests recommend and why.

    If you still don’t have a specific upgrade in mind, you can just ask the manager for “any room upgrade that you think will make our trip even more special and memorable.”

  4. Include a flattering picture.

    Including a nice picture of yourself sets your email apart from >99% of the emails the general manager receives. It also establishes a personal connection.

    The picture doesn’t need to be a glamour shot. But I also wouldn’t send one that might lead the manager to wonder if you’re the kind of person likely to trash a room. Most of the pictures I’ve sent are of my family dressed up on Easter or Christmas. Probably overkill, but if you’re going to do everything else I’ve written above, you might as well go all-in. 🙂

I want to make it as easy as possible for you to compose an email to the general manager that is likely to result in a free upgrade for you. To that end, if you’d like to receive several of the exact emails I sent, just provide your email address below, and I’ll send them to you right away. You can then just choose an email that you like, replace the relevant information with your own, and send it to the general manager:

{{Privy:Embed campaign=331644}}

Conclusion

Can I guarantee that the above steps will result in a spectacular hotel room upgrade for you? No. Am I certain that every element above is required or even meaningful in securing an upgrade? No. Does this whole approach make my wife cringe? Yes. But when we end up in a sweet room, does she love it? Also, yes.

Bottom line, the above process has worked for me 9 times running. It’s the best process I know of. If you’d like an upgrade, it’s certainly worth a shot.

Oh, and when you get the upgrade, thank the manager. Profusely. No matter how much thought and effort one puts into asking, in the end an upgrade is always a gift.

Question: Are there tactics you use to get free or discounted hotel room upgrades? If so, I’d love to hear them. You can leave a comment by clicking here.

If you liked this post, sign up here so that you won’t miss a future post.

Please note: I reserve the right to delete comments that are offensive or off-topic.

Leave a Reply

Your email address will not be published. Required fields are marked *

6 thoughts on “How to Get a Spectacular Hotel Room Upgrade for Free

  1. Thanks for the info. What’s the best time (relative to the stay) to send the email? Should you send it right after booking, even if the stay is months away? Or should you wait until a few weeks before the stay? I’m guessing the manager will have a better sense of suite availability closer to your stay.

    • Great question, John. I’ve done it both ways and found success in either case. So I don’t think you can go wrong.

      That said, I’d lean toward emailing shortly after booking. If the GM replies warmly, you can then refresh the conversation with another email shortly before your stay when he or she will have a sense of the inventory available. If the GM doesn’t reply or doesn’t seem optimistic, then you have more time to try other ways of securing an upgrade.

      In any case, I’d recommend emailing at least a week before the stay just to ensure that the GM has enough time to read your email and act on it.

  2. Just saw this article, thanks for the tips.
    I have an upcoming reward stay at a luxury hotel chain booked using points. It is my first time staying in this chain. Do you think this will matter?

    • Hi Dave,

      My pleasure.

      No, I don’t think it will matter that you haven’t registered stays at that chain.

      This is a different but possibly related point: As I mention in the post, if you don’t have status, I’d suggest coming right out and acknowledging that in the email. I’d say something like, “Given that I don’t have status with Hilton [or whatever], I know I’m by no means entitled to an upgrade. But it would mean an awful lot to me, and if you could provide an upgrade, I’d be extremely grateful.”

  3. You are awesome! I read this a couple days before leaving for Maui. I’m now sitting on the balcony of my 1 bedroom ocean view suite at the Ritz Carlton Maui. Not only did we get upgraded to an ocean view suite from a deluxe king but the manager sent us a bottle of champagne and some tasty cupcakes . I mentioned my birthday and our 34 th anniversary and sent a picture of us then and now . The manager our picture framed and placed in our room ! Great customer service! Thank you so much! I never would have thought of this on my own.

    • Gail, I’m so thrilled to hear it. Thanks for the success story.

      Happy birthday, and congratulations on your 34th anniversary! I hope your time in Maui is amazing.