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How to Get A Luxury Hotel for Cheap

Three expert tactics for never forking over even a dime more than you have to for a room.
How to Get A Luxury Hotel for Cheap

“How the hell do I book a hotel room these days?” 

It seemed like such a simple question my buddy was asking me, yet he couldn’t believe he didn’t know the answer. He’d been trying to book a room for a wedding at the last minute. The wedding party’s discount rates at a four-star hotel were long gone, and now he was scrolling through the pricier less-than-four-star places and getting angrier by the minute. Should he book through Expedia, Orbitz, Kayak, or even Trivago (yeah, the one with that guy)? That’s when I realized: Man, has the “simplest” part of Travel 101—booking your lodging—gotten complicated lately. For good or bad, the ever-increasing onslaught of auction sites, online discounts, travel apps, and, the latest trend, money-back sites like Tingo and DreamCheaper has created a bewildering world of choices.

So I told my buddy: No, the sites he reeled off—Expedia, Orbitz, Kayak, etc.—should never be used to book a hotel room. Here’s why: These “OTAs,” or online travel agencies, operate by undercutting the “rack rate,” the official price displayed on hotels’ home pages, by buying up rooms in bulk at a discount, then selling them to regular travelers like you and me at slightly lower-than-rack-rate prices. 

And while that may seem like a deal, the truth is, you can do a lot better. In fact, the wise traveler knows to always aim for a rate that’s not just less than the OTA rack rate but at least 25% less.

When I told my friend, he was relieved but wary. “Two things are not going to happen,” he said. “I will not get ripped off, and I will not stay at a Holiday Inn Express. OK, so what do I do?” 

That’s easy. Here’s the game plan.

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The only person who can truly influence a hotel rate in any meaningful way is the person manning the front desk, so your first order of business is to call the hotel directly. According to Jacob Tomsky, a former front-desk clerk and author of the hilarious service-industry tell-all Heads in Beds, here’s the right approach: 

Check the OTAs for the ballpark rate, then call your hotel of preference directly. Avoid peak times—11 a.m. checkout, 3 p.m. check-in—when the staff is superbusy. In fact, it’s best to aim for later in the evening, when the duty manager, the highest-ranking onsite decisionmaker, will have time to chat.

Introduce yourself and explain when you’d like to stay, as well as the rate you’ve found on an OTA. Most staffers, Tomsky promises, will respond well to a polite, if persistent, would-be guest.

“We find someone who’s trying to get the best deal more endearing than a guy with a Black Amex, because we can’t afford those rooms ourselves,” he says. “Trying to book cheaply puts you on the staffer’s side.” And even if you get a cheap rate over the phone, keep hustling at check-in by sliding a small gratuity over with your credit card. “It’s an act of kindness—even five bucks puts you above everyone behind you,” Tomsky says. 

At the desk, ask about rates once again. They may be able to offer you a last-minute deal, upgrade you gratis, or throw in some extras. Tomsky himself regularly canceled guests’ first reservations on the spot, then rebooked them at the new rate, which takes only 30 minutes or so to appear in most computerized reservation systems. “I tell them: ‘Go to the lounge, get a soda, and as soon as it drops in, I’ll check you in,’” he says. 

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Sometimes there are dirt-cheap rates hiding in plain sight—you just need to know where to look. 

Take Kimpton, one of the better boutique hotel chains: If you join its loyalty program, Kimpton Karma (it’s free), you can book one of the deeply discounted “last-minute” rooms offered right on its home page under “Last Minute Deals.” Or try HotelTonight, an app that offers bargain rates up to seven days in advance on a cadre of cool hotels. 

If you still haven’t found a deal, head over to the “auction” sites—Hotwire and Priceline—which introduced eBay-style deals to travel but come with one unfortunate drawback: Though the deals can be amazing, you don’t know details about your room or even your hotel till you’ve paid up in full, up front. 

But you can dig them up. According to travel blogger “Johnny Jet” (real name: Johnny DiScala), once you’ve found listings for the destination and dates you want on Priceline—the better auction site, he says—head over to the message boards at “It’s where Priceline users share their secrets about what they booked—what city, what hotel, and how much they paid,” he says. “So you can pretty much figure out what hotel you’re getting from that.” 

DiScala also recommends bidding on boutique hotels only for midweek travel—they tend to be full on weekends, as they cater to vacationers. For a weekend, try low-balling big-chain properties like Marriott, which are filled with corporate travelers during the week but otherwise see lighter traffic. 

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The shortest of shortcuts to a cheaper room is through Tingo or DreamCheaper, the new money-back apps that work as insurance against price drops with a simple premise: You book and agree to pay a rate, while they promise to keep checking for even lower rates, then rebook you and refund the difference. Just make sure you initially book a rate marked “refundable.”

On Tingo specifically, all bookings have to go through the portal on its home page, so you’ll pay the full price up front rather than at checkout. Then if anyone, anywhere books the same room for the same night for a cheaper price, it will automatically refund the difference. Tingo claims that around 20% of travelers receive money back, with rebates averaging $50.

Its rival, the German start-up DreamCheaper, promises savings of up to 15% if you book a refundable room on a hotel’s site and forward the confirmation to The firm built a proprietary algorithm that monitors fluctuating rates and automatically rebooks you—as many times as possible up to the day before check-in—if a cheaper price appears. 

In the end, my buddy got a room at a four-star hotel after all, through Tingo. He paid 8% more than the wedding rate—but that was still less than everyone else. 

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