How I’m spending 4 million Hilton Honors points

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Let’s face it — when comparing Hilton, Marriott and Hyatt points, Hilton Honors points are without question worth the least of the three. Still, with more than 6,500 hotels worldwide, it’s hard to go to a major city and not find a hotel where you can redeem Hilton points.

In the last two years, I’ve earned 4 million Hilton points. While the coronavirus pandemic initially limited my ability to redeem points, once borders began reopening and mask mandates started going away, I began cashing in my earnings before they decreased too much in value.

So, how did I map out my plan to redeem my millions of Hilton Honors points? Let’s dive in.

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How I earned 4 million Hilton Honors points

Before I walk you through my grand plans for my points, I’ll first provide a bit of context around how I came upon such a large sum of points in the first place.

As I was finishing up my degree at American University in March of 2020, I found myself in the same situation many college students across the country were facing: the need to immediately vacate dorms and return home to begin remote classes.

Not long into my time at home, though, I found myself missing the engagement and productivity of my in-person classes. Internet bandwidth limitations made it difficult to have discussions with my classmates and professors, and I missed my friends. It also didn’t help that living three time zones away on the West Coast meant that some classes started at the uncomfortably early time of 6:45 a.m.

Desperate to reclaim at least some aspects of my pre-pandemic college experience, I (along with many of my peers) looked for a way to safely return to Washington, D.C. But there was one problem: Lodging was incredibly challenging to find. Dorms remained closed, and most apartments required 12-month contracts.

Recognizing a potential opportunity to help both students like myself and the devastated hotel industry, I reached out to several extended-stay hotels and pitched the idea of welcoming students looking for temporary housing. After some back and forth, most hotels eventually warmed up to the idea, agreeing to accommodate students for roughly half the price of dorms — and to award me points for each booking.

As I began referring students to Hilton properties in the district, plus locations in Seattle and Chicago, the points rapidly accumulated. Before long, I had secured 300-plus student reservations lasting at least three months for Hilton, resulting in a whopping 4 million Hilton points (or roughly $24,000 worth of points, according to TPG’s latest valuations).

My plan for redeeming 4 million Hilton points

Even though points and miles are a bad long-term investment, I decided to stretch my redemptions out so I could enjoy award stays on vacations for years to come. After all, I worked hard to earn these points.

To get the most value out of my points, I applied three key strategies to all of my Hilton Honors award stays:

Since I have Diamond status through my Hilton Honors American Express Aspire Card, I wanted to try my luck at complimentary upgrades at check-in (one of the perks of my elite status) instead of shelling out more points upfront. I was also keen on maximizing the number of award nights I could get for as little out-of-pocket cost as possible.

The information for the Hilton Aspire card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Related: What is Hilton Honors elite status worth in 2022?

With these booking conditions in mind, I began redeeming points for some stays in the U.S. and abroad.

3 nights at the Grand Wailea, A Waldorf Astoria Resort for 190,000 points and a free night certificate

Located on the Valley Isle of Maui, the Grand Wailea‘s lush resort grounds and sublime ocean views make for the ultimate Hawaiian escape. So, I opted to redeem 190,000 points and a free night certificate from my Aspire card to stay at the property in December of 2020.

While its beautiful setting more than justified visiting, I was admittedly disappointed with the complimentary breakfast I received with my Diamond elite status. The cold, limited selections made this version of breakfast one of the most disappointing I’ve seen throughout Hilton’s portfolio. To make matters worse, the breakfast benefit has since been changed to a food and beverage credit.

Still, with cash prices around $800 per night at the time, I was able to get about 0.8 cents of value out of each Hilton Honors point I redeemed. Plus, I didn’t have to pay the $50 daily resort fee, thanks to Hilton’s policy of automatically waiving the fee on award stays.

Related: Pro tip: Here’s how to avoid paying resort fees

5 nights at the Boulders Resort & Spa Scottsdale, Curio Collection by Hilton for 320,000 points

Eager to visit the Scottsdale, Arizona, area to enjoy some time outdoors, I set my sights on the serene Boulders Resort in April of 2021.

Offering spacious stand-alone casitas as standard rooms, my accommodation felt like a cozy oasis in the desert. The decor was inspired by the property’s surroundings and featured natural elements like wooden beams, Southwestern textiles and local art on the walls. I particularly loved the in-room fireplace and the private terrace.

Another highlight was the property’s setting. The tranquil grounds offered jaw-dropping views of towering boulders. I also encountered cotton-tailed rabbits as I walked around the resort.

By booking my stay with points, I avoided spending $975 per night and was able to enjoy my fifth night free. The points value for this stay was impressive, coming in at 1.8 cents per Hilton Honors point spent.

Related: 4 family-friendly road trips you can take through Arizona

2 nights at the Hilton Moorea Lagoon Resort and Spa for 180,000 points

For my first international trip in 18 months, I decided to stay at the Hilton Moorea in French Polynesia in June of 2021 — and my visit couldn’t have been better.

Choosing less-frequented Moorea instead of Bora Bora or Tahiti made it possible to experience this beautiful part of the world without breaking the bank. I was able to pick from a variety of dinner entrees for on-site meals without spending more than $30 per person, a rarity at resorts on Moorea’s sister islands.

Additionally, I scored a complimentary upgrade to an overwater bungalow thanks to my Diamond elite status. It was nothing short of unforgettable.

Since cash prices were around $850 per night when I booked, I redeemed points for my stay. Each Hilton point netted me about 0.9 cents in value — not bad considering how pricey French Polynesia tends to be.

Related: Moorea or Bora Bora — which island paradise is right for you?

1 night at the Baker’s Cay Resort Key Largo, Curio Collection by Hilton for 60,000 points

While I had high hopes for this property on Key Largo, my stay in March of 2021 did not quite live up to expectations.

I booked several nights at the Baker’s Cay Resort hoping to get an authentic taste of the Florida Keys, but despite some recent renovations, the resort felt too commercialized for my liking. The beach was packed with tourists trying the usual water sports activities (think: Jet Skiing and parasailing), and the food and beverage outlets felt like the stereotypical spots you’d find at any waterfront property. I’d much prefer a locally inspired bistro over a Tiki bar.

The award rate of 60,000 points per night was an incredible deal for a room going for more than $1,500 per night, but even the value of 2.5 cents per point wasn’t enough to sway me to stay. So, I checked out after one night and spent the rest of my time in the Keys at the Hyatt Centric Key West Resort & Spa, which gave me the Florida Keys experience I was looking for.

Related: 9 of our favorite points hotels in the Florida Keys

1 night at the Conrad Washington, DC for 80,000 points

As a haven for diplomats, this property is stunning. The Conrad‘s ultra-modern Scandinavian design is cool yet inviting, making it a place to see and be seen in D.C.

In addition to the hotel’s aesthetic, I loved my complimentary breakfast when I stayed here in August 2021. But I have to confess: I didn’t do as well on this redemption.

The cash price for my one-night stay was $425, so by redeeming 80,000 points, I only netted 0.53 cents in value. However, I was eager to try this hotel without paying out of pocket to do so, so I ultimately decided it was best to make an award booking.

Related: The best times to visit Washington, DC

5 nights at the Hart Shoreditch Hotel London, Curio Collection by Hilton for 179,000 points

Having previously lived in London, I was keen to return to the city once the United Kingdom dropped its last travel restrictions. So, when I planned a trip to London last month, I settled on the Hart Shoreditch for lodging.

Located in the Shoreditch neighborhood, the elegant, modern property (which was recently renovated) boasted proximity to an array of eateries serving curry and pasta — two of my favorite types of dishes. I also enjoyed the decadent Diamond breakfast provided each morning, especially the avocado toast and Turkish bagels.

The highlight, though, was the top-notch service. Every employee I interacted with was friendly and helpful. The front desk agent also upgraded me to a junior suite, which was beautifully appointed and offered ample space to stretch out.

Because I planned a longer stay, I opted to use points instead of paying the cash rate of $1,432 for the five nights. Doing this allowed me to take advantage of the fifth-night-free benefit. Each point ended up being worth 0.8 cents, or a little more than TPG’s latest Hilton valuation of 0.6 cents.

Other hotels I am considering

While I’ve managed to spend 1 million points so far, I still have 3 million points left to use.

By this time next year, I plan on redeeming 100,000 points for a five-night December stay at the Conrad Bangkok and 360,000 points for a return visit to the Hilton Moorea in January for five nights.

Looking ahead, I am also very eager to lock in an award stay at the Waldorf Astoria Los Cabos Pedregal. Since cash rates here regularly exceed $2,000 per night, I’ll likely get more than 3 cents of value per Hilton point spent if I’m lucky enough to find award space. That would easily be one of my best redemptions to date.

Of course, the Waldorf Astoria Maldives Ithaafushi is also on my list, but it’s a bucket list property for many savvy Hilton enthusiasts. After Hilton’s recent devaluation, resulting in rooms now requiring 150,000 points per night, it’s becoming harder to get value from this hotel.

How you can earn lots of Hilton points

I managed to accrue a ton of points thanks to several group bookings at Hilton properties I organized. While my situation was unique, if you’re planning a group event (like a wedding or meeting), see if you’re able to get points for all room reservations included in the rate agreement.

You can also sign up for one of Hilton’s credit cards, which feature impressive welcome offers and earning rates for cardholders.

When I use my Aspire card to pay for Hilton charges, I earn 34 points per dollar spent (14 points from Amex, 10 base points and 10 bonus points, thanks to my Diamond elite status). This represents a 14.4% return on points for each dollar spent with Hilton.

For example, earlier this month, I stayed at a Canopy hotel in North Bethesda, Maryland. Although the cash rate was only $131.30, I earned 2,626 points from my stay with my Diamond bonus, 2,500 from the Points Unlimited promotion, 1,000 as my Diamond welcome gift and an additional 1,838 points by using my Hilton Aspire card for a total of 7,964 points.

Based on TPG’s current valuations, I received $47.78 worth of points for a one-night stay that cost less than $150.

Related: How to choose the best Hilton credit card for you

Bottom line

Hilton points are not worth as much as those attached to other loyalty programs like Marriott and Hyatt, but there are still plenty of opportunities to maximize your earnings with the Hilton Honors program.

Whether you’ve acquired millions of points like me or are just looking to cash in some recent earnings on an upcoming vacation, creating a points redemption strategy early on is a great way to make sure you’re getting the most from your points.

Once you’ve mastered the ins and outs of the Hilton Honors program, you’ll find yourself booking an award stay at one of Hilton’s incredible properties in no time.

Featured photo by Kyle Olsen/The Points Guy.