A new feature on, called "WiseAsk," lets people request in detail what they're looking for in a vacation rental.
By contributor
updated 4/15/2011 9:27:05 AM ET 2011-04-15T13:27:05

When Nicole Hockin vacations in Rome at the end of the month, she will breeze to the front of the security line, jump into a private car from the airport and get a free night at her hotel when she arrives.

Hockin is not a high-powered business executive or a wealthy VIP. The Denver travel blogger is a member of ClearMe, which for $179 a year lets members go through a separate, shorter security lane at airports in Denver and Orlando — and soon 10 other cities. She is also a member of’s welcomerewards loyalty program that lets members earn a free night stay at 60,000 hotels worldwide.

Hockin also just took charge, e-mailing her hotel in Rome and asking for a private car to pick up her and her husband at the airport for 50 euros — about the same amount they would pay to take a train and then a cab to the hotel.

In these days of climbing airfare prices, baggage fees, resort charges and tacked-on rental car surcharges, it’s not easy for travelers to feel the VIP love.

But as Hockin proves, it is possible to put yourself in the driver’s seat in what has become a seller’s market. A little persistence and a friendly smile can help.

“All you have to do is ask,” says Hockin, 34, whose blog,, offers travel tips.

Deals on demand
Loyalty programs can give travelers more leg room and upgrades on airplanes, two-for-one deals at hotels and VIP cocktail receptions on cruise lines. But if you look around, you’ll find a number of other services that still want to schmooze all kinds of travelers.

For instance, travelers call the shots at, a vacation rental site. The site’s new feature called “WiseAsk” lets people request in detail what they’re looking for in a vacation rental — such as “Paris, April, $600, 2 bedrooms, bringing my dog and want down pillows.” Those requirements are then sent out to thousands of property owners, who then bid on your business.

Martha Gillette of Fayetteville, Ga., booked her vacation this month using another site, She says she snagged a deal — $255 for a three-day stay at the posh Sandestin Beach Resort in Destin, Fla. But unlike other discount travel sites such as Priceline and Hotwire, Yuupon lets buyers see exactly which hotel they’re getting, and they can even change their minds. Travelers can cancel, save the vouchers for up to a year or transfer them to family and friends.

When Gillette learned that rain was forecast during her planned trip, she asked Yuupon if she could change her dates to arrive three days earlier. They agreed.

“It’s a rare, rare thing to be able to do what I did,” says Gillette.

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What about me?
Another startup, The MeNetwork, caters to the needs of travelers by letting them do the asking with their cell phones and sending them deals on demand via text message. Travelers in any one of 30 different cities can send a text message with keywords like “Las Vegas deals” or “Omaha happy hour” to the number “63638.” The MeNetwork then sends a few offers like 20 percent off their dinner bill at a restaurant or two-for-one drinks at a bar.

Disney, too, will give customers more VIP treatment with an online reservation system now in the works that will let people reserve ride times at its theme parks from home.

Even Delta Air Lines is giving passengers more say on what it takes to get them to agree to be bumped on a crowded flight. The airline holds Priceline-style online auctions in which passengers say how much money they’d take to be bumped from a flight. They bid using their own computers or at an airline kiosk, and the airline starts with the lowest bidder, and gives the winners “Delta Dollars” — vouchers for future flights.

Business traveler Dave Maney found his own way to avoid getting bumped by an airline — not to mention avoid paying baggage fees — on his recent trip between Boston and New York City. He skipped the airplane part.

Instead of booking a $200 flight, he went online to buy a $15 ticket to ride the BoltBus. By taking the bus, he got more leg room and free Wi-Fi Internet access, and the trip took the same amount of time as a flight, without the headache of going through security, waiting for the plane and catching a cab to the hotel.

“I wouldn’t say it’s for everybody,” Maney says. “But it was way more pleasant than an airline trip.”

Story: Guide to being bumped (or not)

Let yourself be wooed
When it comes to accommodations, many hotels are still willing to woo guests, even though demand is up for hotel bookings. Extras like complimentary gourmet breakfasts, $50 spa treatments or complimentary cocktail hours may actually come with your stay, says Gabe Saglie, senior editor of, which publishes travel and local deals. “It’s about looking beyond the room price.”

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At many hotels, the concierges often hold the key to better service for regular-paying guests. They may have free tickets to museums and shows and first-hand knowledge about and discounts for great restaurants, says Hockin.

Hockin has asked concierges to arrange for taxicabs to be on the corner for her and to deliver a bottle of wine and once, a half a dozen cupcakes in her room upon her arrival. Several times, she’s even talked her way out of paying the daily $15 “resort charge” typically tacked on to a bill upon checkout.

“Let the concierge be your BFF and get to know the staff,” Hockin says.

Video: Learn the secrets of luxury hotel concierges

Other perks can be had for travelers who ask. If you stay at one of the 4,000 IHG hotels, they’ll pay for your checked baggage fees. Kimpton Hotels offers in-room massages and facials, and upon request, will even lend you a goldfish in your room overnight.

At the Benjamin Hotel in New York, the “sleep concierge” will set you up with a bedtime massage, a white noise machine, eye mask, lavender turn-down and a menu of 12 pillows —including the magnetic therapy pillow and the water pillow. The hotel guarantees a good night’s sleep or you get a free night’s stay.

The good pillows are a huge hit for Megan Chandler, an Indianapolis TV executive who sleeps poorly and travels twice a month for work. She stays there — with a memory foam pillow — every time she visits New York City. With some tipping, the hotel staff now knows her name and the front desk manager has even fixed her cell phone for her.

“Pick a hotel you like and make yourself a repeat customer,” Chandler says.

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When Chandler travels elsewhere, she will often call a hotel and ask them to beat the price of their competitors. “When I want a better deal, I ask for a sales manager instead of calling the 1-800 number,” she says.

Travelers can also get more attention — and bigger discounts — by vacationing during a city’s off-season or by staying over a weekend at a hotel in a downtown business district, says Saglie.

“With thinner crowds, you’re getting more attention,” he says.

Checking into your room later in the day can also boost your chances of a free upgrade to a larger room, says Saglie. Often no-shows mean more rooms are available, and just being friendly can go a long way.

“I have gotten upgrades merely because I’m nice and I ask,” Saglie says. “It’s amazing, but it does make a difference.”

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