Free resort upgrade strategy: Book a premium room for part of your stay

Finding and booking a resort hotel can be a frustrating experience, especially for budget-conscious travelers. Very often you’ll see an appealing room rate only to click on it to discover that it’s for a “standard garden view room” at a beach resort where half the point is to look at the water.

We’ve discussed other strategies to get free room upgrades before, and here’s a new one that has worked for me a few times that I’d like to share. The short version is that you book a cheap room for part of your holiday and a premium room for the first or last few days.

Many resorts frequently upgrade anyway

Again, something that happens at many resorts but the public isn’t aware of is that they’ll sell their cheapest rooms up until the whole hotel is sold out. In other words, if a hotel has 40 cheap rooms and 100 premium rooms, they will keep booking the cheap rooms until they have 140 total reservations. If only 70 premium rooms are booked for a night, they will eventually book 70 cheap rooms and then upgrade 30 of the guests.

The reason they do this is that they make a lot more money by filling up the hotel rather than having 30 empty rooms. Of course many hotels have only a small difference in price, so the premium rooms sell out at the same time, but others try to charge a higher premium, and those are the ones where this works best.

Strategy: Book 4 or 5 nights in a cheap room, and 2 or 3 nights in a premium room

So let’s say you arrive at a resort hotel in Jamaica or Cancun on a Sunday, and you and about 30 other people are checking in for the week. Maybe there are 5 couples who will be upgraded to a premium room. They look at all the reservations, and you will be the first in line because you’ve already booked a premium room for the end of your stay.

This way they are only upgrading you for the first part of the week, and they can sell that standard room again for the end of the stay. It’s an easy decision and your chances of getting the best room for the whole week are very high.

The worst case scenario is still pretty good

Obviously there aren’t room upgrades every day, so you might have to stay in a standard room for at least your first day or two, but eventually you’ll still be at the top of the list when your premium room (that you’ve booked for the end of your trip) opens up.

And the worst case scenario is that you stay in the rooms you’ve booked exactly. On your first 4 or 5 nights you’ll be happy in a tropical resort hotel, and on those last few nights you’ll be even happier when you move into a great room. When you leave you’ll feel like you spent the whole week in that nicer room anyway.