Timeshares certainly do have a bad wrap. I am the first to acknowledge that is an often deserved reputation, BUT if you play it right, there are some really good deals to be had. I’ve generally found I don’t spend meaningfully less as a result of timeshares, but I do have meaningfully nicer stays. Once you get beyond the highly effective sales pitches to commit your hard earned money to “an investment in vacation”, that is.
Believe it or not, I am imperfect in my gaming activities, and I will truthfully acknowledge (albeit painfully) that I do fully, wholly, immensely regret the second timeshare purchase. BUT, even with that flawed decision, we have still had good value. Despite being pitched timeshares with just about every company out there (we love the nearly-free travel), we currently own two:
- Hilton Grand Vacations @ 5440 points annually (this is generally 1 week summertime stay)
- Vidanta Legacy @ 2 weeks annually (these are highly flexible)
The reality is there are two components of any timeshare. First is the typically large upfront expense, and the second is any recurring “maintenance” or “usage” fees. Each of the two above is ~$1,500/week for redemption. That stay, though, is typically much nicer/more luxurious, as well as moderately cheaper, than a similar hotel stay.
Let’s start with Hilton Grand Vacations

HGV has quite frankly presented an amazing set of stays over the past five years. We’ve had nice visits in Utah, Colorado, New York, Los Cabos, San Diego, Charleston, Scotland, and in March we’re headed to Maui, and if the redemption gods play nice, Italy in the fall. Half of these stays have been our annual points, and the other half bonus points/perks/upgrades. Unsurprisingly, once you’re hooked in, they always want you to stay more and sell additional points/weeks. But so long as you stay strong, the freebies/benefits of those discussions are worth it.

The redemption for Hilton is generally good, flexible, and self-serve. They have a website where you can see availability, check out different properties (there are many), and manage anything related to the account. Our 11 stays since 2023 have cost us ~$5,600 in dues, and have been ~$15,000 in value. Note, this excludes the actual upfront cost of purchase, which for us was the low-$20k’s range. On average we’ve found a point (we get 5440/year) to be worth ~$0.35.

Would I do it again? Maybe would have played a little harder on negotiating, but yes, we’ve found good value out of HGV.
Next up is Vidanta

First off, what the heck is Vidanta? It’s a “Vacation Ownership” company based out of Mexico. There are a range of resorts, all very good quality, and some version of the same tiered options from basic to ultra luxe.
My family has owned a timeshare based out of Puerto Vallarta (Nuevo Vallarta) for now decades, and I feel like I’ve been going on vacations at Vidanta (Mayan Palace, Grand Mayan, Grand Luxe, Grand Bliss, and now The Estates) for what is my whole life. With my family having the most premium ultra Estates Empire experience, the accommodations are genuinely outrageous and the service is stellar.
That said, there was basically no need for me to buy my own independent ownership, as we already had the best one, and more weeks than we use, ever. Regardless, we had a lovely stay this past month and despite paying *only* $1,500 for the week at the lower tier resort, we were upgraded big time to The Estates experience. Photos below of the room are enough reflection of the high quality, but the perks of private transportation, low (almost no) population pool, and private butler/concierge really adds that extra oompfh. The upgrade was contingent on an “Owners Update”, but we managed that without shelling out big cash.
Vidanta has some varied locations throughout Mexico, including Cabo, Puerto Vallarta, and Cancun areas. Every experience is stellar, and regardless of timeshare ownership or not, they’re great vacations and enjoyable stays. One year I’ll take advantage of the 2-for-1 golf, perhaps.



With all that said, here are a few key takeaways/notes:
- Take the free (or almost free) stuff and enjoy some sponsored travel!
- Do not give in to the salesman pushing, you do not need to buy anything you don’t want
- Do not spend money you don’t have, and never use their financing, even if it seems like a good deal
- If (big if!) you do want to buy, keep saying no, because the best deal will occur as you are walking out the door
- Do not ever waste your time with Wyndham, they will not take rejection well, and there is a good chance they will yell at you (which is quite unpleasant)
