An example of HotelTonight’s New York City offerings. (

A look at the individual hotel display. (

HotelTonight is an app that appeals to a certain kind of traveler — last-minute. It allows out-of-towners to score deep discounts, but at what some would consider a steep price: Reservations can be made beginning a week out, max. We set out to find out what happens when a Procrastinator entices a Planner to book it her “whenever” way.

Andrea: The Planner

It’s 6  a.m. on a Friday in San Antonio. Do you know where you’re sleeping this evening?

I don’t.

It’s noon. Now?

Not yet.

Half past 1?

Getting closer.

3 p.m.-ish.

Yes, finally.

Phew. That was cutting it close — for me.

The travel world is populated by two opposing forces, Planners and Procrastinators. In some categories, such as dining and activities, I embrace my Procrastinator side. In new destinations, I often let the winds of spontaneity toss me this way and that, like a dandelion puff with no set menu or agenda. But for overnight accommodations, the Planner oversees all bookings. I don’t trust the Procrastinator; we might end up sleeping in the bed at a tanning salon. I want — no, need — to know in advance that I have a guaranteed nest for the night.

But then along came a Hotel Procrastinator disguised as a friend.

Alexa is a last-minute booker, and she urged me to join her club, HotelTonight, the app that caters to indecisive, noncommittal, disorganized and/or impetuous travelers — the counter-me. I initially resisted, but then I softened and finally agreed to challenge myself. With Alexa’s encouragement, I invited the Hotel Procrastinator to join me on an upcoming trip to San Antonio. This made the Planner very nervous, but she just had to deal with it.

When HotelTonight launched in 2010, the company took its name quite literally: Travelers could book a hotel only within 24 hours of their stay. About two years ago, the app stretched the booking period to a week. The discounts can rise to 50 percent off, especially with “Geo” rates, which appear after noon on the day of booking. Rates drop even more after 6 p.m. About two-thirds of the app’s users chase the discount rainbow and book on the same day. One potential risk: The rooms can sometimes disappear.

“You want to be strategic,” Tim Lopez, a company spokesman, told me after my experiment. “You are not exactly encouraged to wait till the day of.”

A few days before my departure, and several weeks beyond my comfort booking window, I downloaded the free app and plugged in the destination and date. The preliminary search was encouraging. I noticed familiar names (Wyndham Garden, Hyatt Place) as well as local favorites (Menger, Crockett Hotel). I scanned the mini-bios with pictures and was heartened to see that none of the properties resembled settings for “Cops.” The jaunty write-ups — “Gold (lone) star for the free breakfast with Texas-shaped waffles,” stated the Crockett review — boosted my confidence and resolve. I could’ve booked then and there, but I was curious to see the offerings closer to my night. In the shadows, the Hotel Procrastinator cackled and Alexa beamed.

I began the search in earnest 48 hours before my arrival. I scanned the curated list of hotels described as Luxe, Hip, Solid and Basic. (Total inventory: more than 15,000 hotels in 1,900 cities in 36 countries, all rated above two stars.) I had fewer choices — about 15 properties — than such mainstream sites as and TripAdvisor, but I spent less time agonizing over the options. I mentally circled El Tropicano Riverwalk, for $92 (down from $139); the Emily Morgan Hotel, for the special Geo rate for $149 (vs. $176); and Aloft San Antonio, for $112 (was $149).

On Thursday, the Aloft price dropped to $88 and the Emily Morgan fell to $114. I dispatched the Hotel Procrastinator to fetch me a coffee and motioned for the Risk-Taker to come sit beside me. I was no longer worried about where I was going to sleep; I was now obsessed with the game — or the gamble.

The morning of my stay, I checked the site and gasped with horror: The hotels I had been tracking were gone. Several of the new choices started with La and ended with Quinta, and the rates at a few others had increased. I reached out to Alexa for guidance. She suggested that I book immediately, before the situation worsened. Yet, I had come so far in this exercise. I decided to push it to the brink.

For several hours, I obsessively (and fruitlessly) watched the app for any movement. After lunch, Procrastinator and Planner held an intervention. If I hesitated any longer, they informed me, I could end up at the Holiday Inn out by SeaWorld. And so, I gave in. I clicked on Candlewood Suites and paid $141. At least I had a full-size fridge and free laundry facilities.

The hotel didn’t exactly fit the app’s description. It wasn’t on the Riverwalk, for example. In addition, when I told my San Antonio friend where I was staying, she insisted that I move to a better place. (As motivation, she pointed to Interstate 35, the “drug corridor,” from the parking lot.) She found me a $100 room at the Westin Riverwalk on a site called Angel Buys.

Loyal to the end, I stuck with my HotelTonight purchase. That evening, however, I revisited the app. The hotels I had previously seen had returned. Maybe I shouldn’t have acted so rashly and held out a bit longer.

Postscript: After my San Antonio experience, I have more faith in the Procrastinator but I will still proceed with caution. For an upcoming trip to Philadelphia, I plan to book a week out, a happy compromise for both travel personalities.

Alexa: The Procrastinator

I was about to crash on a friend’s couch in New York City when I took a quick glance at HotelTonight’s selections — just in case. Vivid images of hotel rooms filled the screen alongside prices I could almost convince myself were affordable. Did I really want to squeeze into my friend’s one-bedroom apartment, which she shared with a roommate who slept on the other side of a semi-permanent divider? Or did I prefer the idea of a big, fluffy bed, space to spread out my stuff and my own four walls?

I booked a room at a Hampton Inn for $113.

That was two years ago, and I’ve used the mobile app a handful of times since then, in locations as far-flung as Los Angeles and Portland, Maine. I’ve relied on it for last-minute getaways and on trips when I preferred to have my own accommodations instead of sharing with friends or family. Recently, I used the app for a visit to Philadelphia with my sister. I couldn’t make up my mind about whether I wanted to stay one or two nights, and the app gave me the flexibility to feel out my day — who would be joining us, for example, and when were we planning to leave — before making a decision. I booked once I had all the details.

I’m not looking for a luxurious night at a boutique hotel and spa, which you can find on HotelTonight, but a mid-priced room with an adequate bed and maybe, if I’m lucky, free breakfast. (Yes, I’m a sucker for free food and WiFi.) The app’s mobile design allows you to scan hotel amenities, including parking, which is why I picked the Rodeway Inn Center City in Philadelphia. The $15 overnight self-parking won me over. What my room lacked in windows (zero), the hotel’s location made up for: The property was around the corner from my sister’s hotel and within walking distance of Reading Terminal Market. No free breakfast, but the $176 rate included WiFi.

Don’t get me wrong. I’m not totally at ease during this process. I now check the app ahead of time to get a sense of the possible cost. Sure, I might save a few dollars if I planned ahead and secured a room through Airbnb. But I fit the app’s target demographic: travelers who don’t initially intend to stay at hotels. When I studied abroad in Europe as a college student, I wasn’t fazed by sharing a house or a hostel room with friends. I still crave the spontaneity of cheap travel, but when the idea of a lumpy couch or cramped space starts to become a reality, I log in and start swiping. With last-minute booking options, my failure to commit to overnight getaways, or to switch off the college mind-set, never winds up being a cautionary travel tale.

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