How to Land Posh Hotel Upgrades for $20

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Frugality gets a bad rap. While it's not as bad as being "cheap," frugality is often seen as going hand in hand with a life free of luxury and a disdain for all nice things. And while my husband and I try our best to live frugally, we also like nice things. So when describing our spending philosophy, we prefer the term "money savvy." Money savviness means getting more for our money, whereas frugality often equates to just spending less. And one of our favorite ways to be money savvy is the $20 hotel trick.

What if I told you that you could get a deal on your hotel room, and for a mere $20, you could also get a swanky upgrade? Well, I just told you. And it's as awesome as it sounds.

The $20 hotel trick is geared for hotels with premium rooms (think four- and five-star resorts) in major vacation destination cities. The tactic is most commonly in Las Vegas, but other cities like New York, Los Angeles, Chicago and Atlantic City may have prime hotels where you'll find success. Here's how to score your upgrade:
  1. Search for hotels in your destination city that have great deals on standard rooms and also have upgrade options. Remember, you want to pay for an average room and get upgraded to an awesome room. And if you're really feeling frugal savvy, save a few more bucks by using Priceline Negotiator or Hotwire and use these tips to book your hotel.
  2. Upon arriving at the hotel, prepare your "$20 sandwich." Take a folded $20 bill and slide it between a credit card (on top) and your driver's license (on the bottom). Others prefer to simply wrap their credit card with a $20 bill, but we prefer to be more discreet. After you've constructed your sandwich, place it in your pocket.
  3. Go to the front desk to check in. We do our best to act friendly and warm with the desk attendant to start things on the right foot. During the check-in, we hand the desk attendant our $20 sandwich and ask if there are any complimentary upgrades available.
  4. Now it's time to await the verdict. If everything works right, the attendant will hack away on the computer for a few moments and let you know that today's your lucky day and an upgrade is available -- while slipping the $20 bill in a pocket. And if you're not so lucky? The attendant will slide your card and unaccepted Andrew Jackson back across the desk. No harm, no foul, but no upgrade either.
So why doesn't it work all the time? There are lots of reasons, the most common being that there aren't any upgraded rooms available. You're less likely to succeed on busy weekends or holidays. And while many hotels encourage employees to upgrade guests at their own discretion (compensated or not), others have policies that discourage them from pocketing tips.

We've gone three for three with our attempts in Vegas, averaging over $75 a night in upgraded room savings. You can see how other travelers have fared. While results vary, there are enough success stories that end in penthouse suites to convince even the most timid to give it a shot.

Have you tried the $20 hotel trick? Any pointers or success stories you'd care to impart? Let us know whether or not you have the stomach to serve up a $20 sandwich.

How to Land Posh Hotel Upgrades for $20

Remember what your parents told you to do when you were bored? That's right: Go outside and play. Not only is this an important lesson for kids –- finding ways to have fun using only your imagination –- it's free. It's easy today to get caught in the trap of spending money to entertain our families, whether it's buying an smartphone app, spending money at the mall or the movies or buying new toys. These are fun treats every once in a while, but keep it to a minimum and remind your family of the great outdoors.

Libraries are fighting to stay relevant in today's technology-centric society, so why not help them out while you save money on books and entertainment? Library cards are still free, and your taxes pay for these resources. Borrow books as well as DVDs of movies and television shows and cut back on your digital purchases and on-demand subscriptions.

Before you protest, this is definitely a major lifestyle change if you already use a smartphone regularly, but worth considering if you want to save a lot of money each month. Opting for a phone without Internet access –- or even a pay-as-you-go phone, if you rarely need to use it –- will cut costs; it might offer the added benefit of unplugging from constant connectivity.

Carpooling became popular during a countrywide effort to save gas in the 1970s, and today there are signs of resurgence with technology that allows commuters in the same area to easily find each other. If you don't have the option of public transportation, search in your own community for carpooling groups or talk to your coworkers to figure out a schedule.

Commit to skip the expensive salad bar or lunch spot across the street and pack a bag lunch at least three or four days a week. This can add up to a lot of money saved over time. 

While you don't need to use a pencil and paper to write down every purchase as was done years ago, the routine of tracking everything you buy can be an important habit for more careful spending. If you'd prefer to stay digital with this tactic, use Excel, Google (GOOG) Docs or an online tool that collects your daily transactions and sorts them for you.

This concept is no stranger to those who lived during economically challenging times years ago; if you didn't make enough money, you simply found another job to boost your income. Today, while job availability, familial roles and time commitments differ greatly from back then, you can still look for additional income opportunities. Freelancing is one option for those that need to spend time at home with family; you can also find seasonal opportunities in retail.

Take a tip from earlier generations and make your contributions to savings accounts the same, rather than adding more or less depending on other unexpected expenses. This might mean rethinking the amount you put away each month; even if you lower it, more regularity over time can have a bigger impact.
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