Best strategy for getting room upgrades at resort hotels

Most of us check resort prices on the internet, and are disappointed to find that the amazing promotional rates we are seeing are actually for the worst rooms at a resort. It’s understandable if you think about it, and sometimes the better rooms are only a small extra fee, but other times they are much more expensive.

There are a couple of tricks that experienced travelers know to get the better rooms for a lower price, which I will discuss below. As always, being flexible is the key to getting the most for your travel funds.

Trick 1 – Look for resorts with small numbers of cheap rooms

This might seem a bit complicated at first, but it really works. At most resorts the Ocean View rooms are the most expensive and the Garden View or Pool View rooms are cheaper. What isn’t well known is that many resorts only have small numbers of these Garden View rooms that are used as a Bait and Switch, for lack of a better term.

You might see a resort in Cancun that has rooms for US$199 per night, and when you click you see those are Garden View, while the Ocean View rooms cost US$249 per night. They know that as long as the difference in price isn’t too much, that most visitors will end up booking the Ocean View room. In fact, they might only have 20 Garden View rooms and 100 Ocean View rooms, so it’s important for them to book the better ones.

This is where you can come out ahead. These resorts will almost never actually run out of the cheaper rooms because if they did, their listing on booking sites would show them as more expensive overall. So what they do is they’ll just keep booking the cheap rooms until every room in the resort is gone, and many people get the free upgrades.

So the trick is to find resorts that only have a few of the cheap rooms, and book one of them. You’ll obviously get the lowest price, and there’s a pretty good chance you’ll get upgraded when you check in as well. It might not hurt to tell them it’s your anniversary or something when you arrive.

Trick 2 – Travel just outside the high season

Let’s say a hotel in Jamaica has 400 rooms. In January they will almost all be full every night, but in November or in April they’ll be half full at best. Once again, the trick is to book the cheaper rooms during a time you know they won’t be very full. When you arrive there is a very good chance you’ll get a free upgrade because the resort has a lot more to gain by making you happy.

These resort managers are smart and they know that it doesn’t cost them any more to clean an Ocean View room than a Pool View room, and the chances that you’ll give them a good review and come back the following year are greatly increased.

With both strategies you have to be prepared to stay in the cheaper room, or perhaps pay for an upgrade after you check in if the trick didn’t work.

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