Travel Till You Drop Logo

Play the Timeshare Game and Win: Tips for Getting Best Deal 2023

Play the Timeshare Game

How to Play the Timeshare Game (and Win)

Certain companies, such as Marriott and Hilton, and many others, frequently offer timeshares at resorts that are not typically part of their primary hotel locations. Large hotels frequented by tourists have their division of timeshare affiliations. These big hotels include Hilton Grand Vacations, Hyatt Residence Club, Holiday Inn Vacation Club, Marriott Vacation Club, and Disney. 

A timeshare, as most of us know or have had a bad taste in our mouths as we say it, is a concept where property ownership is shared and where one may utilize a vacation property for a specific period each year. Timeshare properties can include resorts, campsites, and condominiums, among others.  Timeshares can be very effective.  While not for everyone, it could be a very effective solution for individuals or groups with a favorite place to return to their favorite vacation spots every year.

Hyatt Residence Club

What Not to Do!

I will 100% tell you I am not a fan of timeshares, so my advice may be “mildly” skewed.  I believe no matter what the representatives suggest, the “fine print” will always get the best of you if you choose to “invest”.  While I am not a fan (especially of the HILTON HGV time share… DON’T DO IT), I do have a few strategies if you are choosing whether to attend a presentation or even purchase a timeshare.

Traveling USA From Turkey: Unexpected Surprises and Tips for Your Trip

How the Timeshare People Scam You

Over the past several years, I had the experience of visiting several timeshare presentations and making that huge error in judgment to purchase one based upon asking very specific questions and receiving the answers I needed to hear.  Needless to say, once you sign the paperwork, if you didn’t have the salesperson’s lies in writing, they never happened, and then you have to fight for years to get out of them.  

Even when you pay the timeshare off in full, you are still required to pay a serious amount of taxes on the timeshare every single year.  So, while the deed could cost you $7K a year, you still can end up owing $600+ in taxes every year.  So, for a 5–7-day slot for a year, you’ve already paid the total, and you’re going to pay for it again with the taxes.  

Traveling USA From Turkey

In addition to the payment of the deed and then the taxes, you will also find that the quality of the properties offered are nowhere near as nice as the traditional hotel.  Also, they will mention the perk of the fare of the reduced amounts on affiliated properties of which they have a telephone book full of them.  

The problem is, they are generally not in areas that they are needed, they are not the nicest properties, and they add on top of that, you can get nicer hotels for the same rate you would pay their reduced priced on, and there are very few dates. You may even here such things as “There are no black out dates”.  This may be true, but the question is, how often is there availability?  

If you ask them, they will tell you “All the time.”  Let’s just say-that would be a lie. Essentially, I tried to use Hilton’s reduced rate program at their RCI properties.  At most, I could find 5 days together and they definitely were not in the places I needed them to be.  As I travel a ton, my plan was to use the reduced-rate properties in downtown Dallas, where I’m from, and use it as my short-term apartment type of stay until I was ready to go to the next place.  

I was thinking to stay there for 3 months at a time and move to the next spot.  The salesperson with Hilton’s HGV program “guaranteed” me this was not a problem.  Then, after the signing and returning home to try to do so, I found the availability to be so short that there was no way this was an option.  After calling their customer service and my salesperson, I received the “Who told you that you could do that?”

They weren’t willing to budge one bit to make good on their words.  So, the next step, I want to sell it as it had no value to me as a once-a-year property.  Let’s just say, to sell it, after the 3-day window of regret, you will lose 80-90% of the value you paid for it sitting in that preview and purchasing.  When I heard this, my mouth dropped!!!  I was livid!   Not only had I taken the time to write down and ask those informed questions, but I was also not planning on being so blatantly lied to.  So now, what?

Well, if you paid for it upfront, you can’t sell it, and they very politely blow off your calls and tell you how sorry they are that they can’t help you with buying it back or selling it for you, what they can do is upgrade you to something where you have more points.  OMG…did they just offer to put me further in debt for some tiny upgrade on a deed that has $0 value?  

Yep, they do have the audacity to do that.  Then then next step—well, you can try to take them to court, which I’m sure somewhere in that 30-page teeny tiny fine print document it says “sucker, buyer beware and we’re not giving you your money back.  Or you can hire a timeshare lawyer to get you out of it.  

So, now that you’ve already paid off your timeshare, paid the taxes for the first year, now you have to pay the lawyer to get you out of it for several more thousand dollars. What do you end up with in the end, a negative $10K or more in the hole of course with a 1 week stay at one of their crappy properties and years of waiting to see if the company will release you from your contract.  

It may or may not hit your credit, but at least it keeps the company from bothering you constantly to pay, pay, pay.  So, over 2 years into this process, I’m still not released from the contract.  Good ole Hilton can take their timeshare and shove it.

So, here’s for a bit more of the technical information before I tell you how to Win at the timeshare game. 

While, I would 100% recommend saying no to a timeshare in most circumstances.  To help you get through the sales pitch unscathed by learning how to get to the “NO” in the timeshare game, I’m sharing this article on how to do just that. 

There are two main types: deeded-week timeshares and points-based timeshares.

  • With point-based timeshare programs, you earn points every year. These points can be redeemed for free stays at your timeshare.
  • With deeded-week timeshare programs, you get a week that you can stay in your timeshare every year.

Timeshares are also flexible depending on the location you intend to visit. This flexibility is achieved through programs that allow timeshare owners to swap their timeshares for another property in a different destination or at a different time of the year that is convenient to them. 

With these programs in place, you do not have to stay glued to your timeshare property, as these might limit your chances to cost-effectively enjoy your vacations in other locations.  Just determine what type of timeshare you would like to visit before you say yes to anything to know what you would be getting yourself into. 

An excellent way to play the timeshare game is by attending timeshare presentations and previews. Due to the competitive nature of the timeshare market, most timeshare programs and vacation clubs will try to entice you to purchase one of their properties by introducing you to their timeshare program through incentives and other vacation packages. 

These incentives may include tickets to a show, stays at their properties for several days, and bonus reward points from their affiliate hotel reward programs. Accommodation incentives comprise standard room packages that can be upgraded.

swimming pool

How to Win at the Timeshare Preview Game

To benefit from these “perks” you and your spouse, if you are staying together, will have to attend a presentation on the timeshare program while are touring the property.  Single members do not have to bring anyone along to these presentations. If you have 3 of your other girls with you, it’s not a bad girls’ trip when you have one person willing to do the hour-and-a-half preview.  

When offered at stay, you will need to meet certain criteria, such as a certain income, and validate that you haven’t attended one of their presentations in a set period of time (aka past 6-10 months). During the sales pitch, the sales agent will introduce you to their timeshare program, how flexible it is, how easy it is to use, the period of enjoyment that comes with the program, and a tour of the timeshare property.

If you consider taking advantage of a timeshare presentation as a practical travel hack, you should also know how to find them and sign up for the offers.

hotel recently Booking

The best and easiest way to identify these timeshare presentations is by searching and checking vacation clubs’ websites. Most Vacation clubs have an online form or a phone number that you can fill out or call to get more information or insights. Some vacation clubs, such as Hyatt, allow you to book the packages online.  Heck, you’ll get a number of those spammy phone calls if you’ve stayed at their normal hotel recently as well.  

When you are ready for it, take the time to listen to the spiel.  Many times, you can get a 4–5-day vacation for pennies on the dollar. I believe the last time I was called; it was for a 5 day/4 night vacation in Cancun on the water for \$299 to start.  After negotiating, I was able to get that down to $199 for the stay.  The way to negotiate, tell them no on the phone; that won’t work. They’ll ask you many times over what the holdup is and why, and you can tell them.  

They’ll go back to their managers and do the old car salesman deal to “see what they can do”.  Make sure you ask if there are any additional resort fees/taxes etc. in addition to the $199/$299 stay.  The salespeople on the phone will at least have to go research and tell you as the line is recorded.  Also, another important tip ***once the total is negotiated, ask them how many reward points comes with the presentation.  

Many times, Hilton, or Marriott, I can’t say for sure on the other ones, but for these, I know these do offer 10-25K points to do the presentation on top of the cheaper cost of the stay.  So, hey, ask—what can it hurt?   They want your business, and you want the vacation.  Other originations, such as Disney or Hard Rock, may give you vouchers to use at the hotel for a variety of things.  

Vegas is definitely a place where you can possibly get those tickets to a particular show you’ve wanted to see.  So, use the system to its fullest and don’t leave anything on the table. 

How to Win at Buying a Timeshare

Well, step 1: You don’t!  Just don’t.  But if you do… do not buy it direct from the company!!!  I cannot emphasize this enough.  My tip of the day: Go to eBay and type in the timeshare you are looking for, and wait for the magic to happen.  If you know, you want a Disney timeshare. Or a Branson, Missouri timeshare, or a Vegas strip timeshare, just type it in and see what pops up.  

So many people are trying to offload their contracts so they don’t end up having to pay a lawyer to get rid of it or end up with this negative on their credit report that they are selling them, literally for 1 penny!!!   Go look, I dare ya.  Once again, my mind was blown.  

So, my naive self sat through this awesome, outstanding, terrific timeshare presentation where the lady talked about her dying father and how she wished she could have taken him on all of these trips before it was too late, making us cry (she was GOOD, I tell you), so that the emotion took over and whoops, there went $7k.  

It wasn’t just the story.  I thought I did my due diligence and asked all of the questions I needed to, but you can’t fight those willing to lie straight to your face.  So, with that being said, maybe I wouldn’t have felt so bad about it if I had gotten that same 1 week a year deal for 1 penny and then just had to pay $600 a year in taxes.  

Five days in a decent enough place for $600 a year for a vacation seems reasonable, but then you may have to be okay with going back to the same place every year. 


So, to conclude this story of woe, you can win at the timeshare game if you really take the time to learn your facts (now that you have an idea of what information you actually need to know going in).  

Go to the presentations, research which ones you want, really use those specials to your advantage, negotiate them further, and if you choose to buy, never ever go through the property itself; Go eBay it’s your birthday!  Also, make sure to note if the company brings you into an hour-and-a-half presentation and they go over—you can get up and Leave!  

90 minutes is what they told you for the presentation perks. If they try to hold you, find a way to get your slip validated – and get out!  So, if you haven’t tried to utilize the timeshare presentation packages, the good news is that it’s never too late to get into the game-just make sure you know which game you are playing!   Hope that helps you never to get scammed (especially by Hilton).

So, no matter where you choose to go or if you decide to buy a timeshare, always remember to Travel Till You Drop! 

About Jill

Hi, Jill Here

Hi! I’m Jill, a Dallas, Texas girl traveling the world. After a career in the Air Force and touring over 50 countries later, my need to explore keeps going! It’s time to rock & roll and find all those places I never knew I was missing.

Join me to get exclusive travel tips, giveaways and more!

I only recommend products I would use myself, and all opinions expressed here are our own. This post may contain affiliate links that, at no additional cost to you, I may earn a small commission.