The 6 Biggest Myths About Hotel Room Upgrades (And How to Score One)

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As we know firsthand here at Oyster, not all hotel rooms are created equal. It’s been a longstanding part of the industry that hotels and resorts, at their discretion, can offer guests a hotel room upgrade. However, talking your way into a hotel upgrade requires a lot more than an extra dose of charm as you approach the front desk -- and, as it turns out, getting an upgrade is more of an art than a science. 

While no one is outright entitled to a hotel room upgrade, at the end of the day, “It's in [hotels’] interests to give you the upgrade and take the best possible care of you and create a memory,” says Alex Miller, CEO of Upgraded Points. But there are definitely right ways and wrong ways to go about nabbing that fancy room -- read on for some of the biggest myths about hotel upgrades, plus how to actually score one. 

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Hotel Room Upgrade Myth: Celebrating a special occasion is a sure-fire way to get an upgrade.

The Galaxy Sanctuary at the Jade Mountain Resort
The Galaxy Sanctuary at the Jade Mountain Resort/Oyster

If you’re planning a special trip or staycation to celebrate a birthday, anniversary, or honeymoon, it might seem like a good idea to see if you can get a hotel room upgrade. After all, it’s a festive celebration, and chances are, the hotel has some empty suites anyway. Right? Maybe.

“The bottom line is that hotels want to take care of people who are celebrating,” says Miller. “The nicer (in terms of luxuriousness) the hotel, the more likely they will give a hotel room upgrade.” He gives the example of a mid-range hotel, where there’s just not much available for guests to upgrade to in terms of fancier room types and plush amenities. 

However, as former flight attendant Philip Weiss told Oyster.com, don’t expect an upgrade just because you say you’re celebrating. Instead, it’s likely the hotel might just turn the tables: “The hotel staff will likely try to upsell you on that overpriced ‘romantic’ suite with full-hotel amenities included.” 

Should something go very wrong during your stay, though, definitely inquire about bumping your quarters up a bit. “The only real way to get a hotel room upgrade is if something is broken in the room you paid for or you suffered some traumatic experience or personal loss during your stay,” Weiss says. “I have heard of this happening to a friend that came back to their hotel room at 2 A.M. to find that it had been double-rented and there were strangers sleeping in their bed. They got a lot more than a room upgrade.” 

Hotel Room Upgrade Myth: It’s easier to get an upgrade if you’re only spending one night. 

Au contraire. Even though you might think it makes more sense for a hotel to grant an upgrade request if you’re staying just one night — given it loses less money on not having a paying guest take the fancy room — those who are staying for multiple nights might actually have a better chance of getting upgrade. 

Why? Think about the services a hotel offers in addition to rooms. Is the hotel or resort known for its spa? Bar? Restaurant? Chances are, the longer you stay, the longer you’ll be spending money on those amenities, which more than makes up for the comped room upgrade. 

Miller agrees that the chance of a hotel room upgrade gets higher if you’re not just there for a night. However, “if you’re there for multiple nights, the chances certainly increase as you’re likely to spend quite a bit (of money) at the hotel, especially on a honeymoon where couples tend to throw the usual budget out the window,” he says. “Hotels know that very well.” 

Hotel Room Upgrade Myth: If you check-in to a hotel at a certain time of day you’re more likely to get an upgrade.

One Bedroom Water Retreat
The One-Bedroom Water Retreat at the Soneva Jani/Oyster

“This myth links back to receiving an upgrade for celebrating a special occasion: The more you communicate ahead of time, the more likely you are to get that upgrade,” says Miller. However, he says, there are certain times of the day you might be less likely to get an upgrade. 

“Don’t rock up to the desk Sunday at 12pm at a city hotel and request one, as everyone wants a late check out at that time,” he says. “The best times really depend on the location of the hotel.” If it’s a hotel for business travelers, it might be busy during the week and emptier on weekends. If it’s a hotel primarily for vacationers, it might be more seasonally dependent than day-to-day. “Remember that Saturdays are often change-over days and when lots of groups come in for holiday stays, package holidays, and so forth,” he adds. Think it over, and plan your hotel room upgrade request accordingly.

Hotel Room Upgrade Myth: All the rooms are full.

Not so fast: If the front desk says they don’t have any rooms available for an upgrade, there’s a chance that some might simply be rooms that are “out of service” — and you might be able to negotiate an upgrade with them. And no, this doesn’t mean you’ll be dealing with a broken shower, says TravelFreak CEO Jeremy Foster. 

“Hotels will have rooms out of service for repairs, and won’t list these as available on their website or other booking sites,” he says, citing that these rooms’ issues are “non-essential” to a stay. “Some of these rooms may only have small issues, such as no remote control, a smashed light, or a broken table leg.” 

“Most of these rooms tend to be upper-tier, too,” he says. “I’ve noticed most of the rooms that are cordoned off are premium rooms, as people who pay those prices expect rooms to be perfect, so any issues and they are closed down to save on any complaints or branding issues,” he says. 

He adds you can sometimes even negotiate a whole stay for free by taking one of those rooms: “You can use the fact that you will be purchasing from the hotel — the bar, restaurant, spa, and other amenities — so the hotel will be benefiting financially from you staying.” 

Hotel Room Upgrade Myth: The best time to snag an upgrade is when you’re checking in. 

The Deluxe Room at the Hotel Raphael
The Deluxe Room at the Hotel Raphael/Oyster

Miller says that the decision on a guest’s upgrade is almost always made at the front desk before they check-in, so don’t expect an upgrade day-of — although if the hotel is wide open with rooms, that may be a different story. If the hotel is tight on availability, the decision might have been made a few weeks prior. “The more time and prep they can have, the better chances you’ll have [of getting the upgrade],” says Miller. “[Asking] last-minute, as you check in, will give you the smallest chance possible.” 

“Write to hotels well in advance as soon as you’ve made the reservation — hopefully weeks in advance,” he says. “Make it clear what you’re celebrating, and politely state what you’d like if possible. Some things are way easier for them to organize too, such as a special amenity or a room with a view versus something that may cost them a lot more, like multi-level upgrades.”  

Even if you’re letting them know quite far out, it’s still good to be as specific as possible with your arrival details. “Tell them what time you’re arriving so that they can be prepared for your arrival,” says Miller, giving the example of guests checking in at 11 p.m. only to find a watery bucket of Champagne that’s been waiting in the room since mid-afternoon. He adds, “Giving them a time will potentially stop them from giving away the upgrade to someone else.” 

“The key isn’t so much the time, it’s the prior planning, clarity of what you’re looking for, being clear what you’re celebrating and plenty of notice — and share when you’ll arrive,” he says. 

Hotel Room Upgrade Myth: If you’re asking for an upgrade, you might as well mention your room preferences.

The best way to ask for a room upgrade is to keep things pretty open-ended — the less flexibility you give the front desk, the less flexibility they have to give you an upgrade.  

At 25hours hotels, Chief Brand Officer Bruno Marti says the following rules, in order, apply for determining who gets an upgrade: They’re a “regular guest, those who booked directly with us, and nice people,” he says. “It’s as easy as that.” 

However, he mentions, “There is one thing that makes an upgrade virtually impossible: special wishes. If you have preferences for a room you’ve booked and are paying for? Usually that’s just fine. If a guest wants a room on a high floor, far away from the elevator, with twin beds, and a south-facing window…we are happy to make this possible within their booked category,” he says, before reiterating that asking for all this plus an upgrade at check-in is just too complicated. “The larger suites available will probably not have all features needed — therefore those guests are never considered [for an upgrade].” Stay flexible, get upgraded — maybe.

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