After diligently planning, reserving, and saving up for that dream vacation, it’s finally time to go. And while you’ve worked hard to get there, that upgraded suite is just a little out of reach. Wouldn’t it be nice if you were able to get that upgrade for free? Turns out, you may actually have a good shot at doing so. All you need to do is follow the advice of some professionals and maybe, just maybe, you’ll get that bigger hotel room for free. Here’s how.
Make a human connection.
Steve Griswold from Pixie Vacations knows a thing or two about how to impress a front-desk agent. After all, he once manned the desk at Disney’s Grand Floridian Resort. His best advice? Just ask, but be nice about it. “One thing I always told guests is to check in at the front desk in person,” he shared with Travel + Leisure. “I know you can check in online, go right to your room, and never see or speak to anyone, but doing it in person allows you to connect with the [agent] one-on-one at the resort.” He added, “When checking in at the front desk, you can always ask if there’s anything else available, or drop that hint about a special occasion.”
Have your travel agent give it a try.
Working with a travel agent? Great. According to Griswold, you can ask them to do all the hard work when it comes to securing a bigger room. “A travel agent can contact the hotel directly or speak with the hotel managers about a couple checking in on their honeymoon, or a special event group staying at the resort, which can help,” he said. “A free room upgrade is never guaranteed, but you want to align as many things as you can to get the best opportunity for some extra magic to happen.”
Join a loyalty program.
Being loyal to one hotel brand can work in your favor in the long run, according to Carina Radonich, a hospitality pro and the co-owner of Magic Moment Resort & Kids Club.
“Guests who book directly with the hotel or are part of a loyalty program are more likely to be considered for complimentary upgrades,” she shared. “From a hotel’s perspective, these guests show commitment, and when inventory allows, we love rewarding that relationship.”
That, and as Radonich explained, you can try using points and your elite status to get that room. “Guests who say, ‘We’re flexible—whatever works best for you’ make it much easier for the hotel team to say yes.”
Try booking in the offseason.
We at T+L are big fans of traveling in the shoulder season. Not only can it help you find better deals on flights and accommodations, but as John Kennedy, the general manager of Kenwood Inn & Spa, said, it could help you nab that freebie upgrade, too.
“Booking midweek stays, especially in the offseason, will increase your chances of an upgrade,” Kennedy explained. “And booking in advance is always a good idea. At Four Sisters Inns, we prioritize returning guests who booked further out as we get closer to the check-in date, especially when it’s a getaway for a special occasion, like a birthday or anniversary.”
Don’t book the cheapest room possible.
Louise Belisle, owner of Ottawa Luxury Travel at Trevello Travel Group, wants you to know you don’t need to haggle with the front desk or really try any of these hacks if you don’t want to. These upgrades, she said, are the “outcome of how a guest is booked, profiled, and prioritized before arrival. Hotels allocate larger rooms based on availability, length of stay, booking channel, and the guest’s overall profile—not on ‘magic words.'”
So, how then do you stand out at booking? It’s simple: Just don’t book the cheapest possible option for a room. Go for something baseline, but not basic, because, just like how you become ineligible for an upgrade on many airlines when booking basic economy, the same goes for hotel rooms, too.
“At the booking stage, reserving a reasonable base category, rather than the cheapest room, gives hotels flexibility to move up guests one level if inventory opens,” Belisle said. “Requests like corner rooms or higher floors only help when those rooms fall within the same coded category.”
Additionally, she encouraged everyone to book directly through the hotel’s website, which better allows hotels to recognize the guest in advance. “That’s why travelers who book directly with the hotel or through a trusted travel advisor are far more likely to receive discretionary benefits like better room placement, larger accommodations, or added amenities when availability allows.”
If all else fails, slip them some money.
Brandon Crudup, general manager at Station House Inn, wants you to know if all else fails, “a $20 for the front-desk staff can work, too.” OK, so he shared this as a joke, but you never know, this old-school trick could work. As for his honest advice, Crudup said you can chat up the front-desk associate and ask “what room is their favorite, and then ask for that one. Specific, friendly requests are more effective than vague ones and can potentially lead to that upgrade.”
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