3 Hilton award stays I'm booking now to save on future travel

I've typically struggled to get great value from Hilton Honors points. After all, Hilton Honors doesn't have an award chart and instead uses dynamic pricing. As such, you'll usually get relatively consistent value from Hilton points when redeeming for Hilton stays. Based on TPG's valuations, you should generally aim to get a redemption value of at least 0.6 cents per Hilton point.

But I've noticed less-expensive Hilton award nights in many destinations on recent searches. And I obtained a redemption value of about 0.68 cents per Hilton point on several awards I booked or considered booking recently. In comparison, most of the Hilton redemptions I booked or considered booking in the past provided closer to 0.6 cents per point in value.

So, for multiple reasons, I believe now is an excellent time to book Hilton award stays. I'll start by explaining this belief and why I typically haven't redeemed Hilton points for past stays. Then I'll describe some Hilton awards I've recently booked as well as several awards I may book after earning more Hilton points.

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Why I previously haven't used Hilton points

When redeeming points and miles, I typically aim to get at least TPG's valuation. TPG values Hilton Honors points at 0.6 cents each. However, I've struggled to find stays where (1) a Hilton property is the best option and (2) redeeming Hilton points is the best way to book.

In fact, until we redeemed 29,000 points for a Saturday night stay at the Redmont Hotel Birmingham (part of Hilton's Curio Collection) last fall, my husband JT and I had never stayed at a Hilton property using points. Sure, we'd made many bookings using Hilton points. But, in each case, we'd either canceled the trip or found a better way to book. For example, when we stayed at the DoubleTree Resort by Hilton Fiji, I originally booked using points but subsequently switched to a paid rate.

Hilton's fifth night free on awards for elite members is a compelling way to maximize Hilton Honors redemptions. After all, it's easier to get at least 0.6 cents per point in value when you're getting the fifth night free. But we haven't stayed with Hilton frequently in the past. And when we have stayed with Hilton, it's usually been due to a compelling rate or promotion.

Plus, the earnings on paid Hilton stays are compelling. Between 14x earning at Hilton properties on the Hilton Honors American Express Aspire Card and 20x earning at most Hilton properties as a Hilton Diamond elite, we can get a massive 20.4% return on most Hilton paid stays (based on TPG's valuation of Hilton points at 0.6 cents each). This rate of return when booking directly with Hilton is challenging to beat. 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: 5 ways Hilton Honors should improve its loyalty program

Why now is a great time to book Hilton Honors awards

Despite my struggles to redeem Hilton Honors points in the past, I've found some good redemptions for trips in mid- to late 2021 and early 2022.

After all, paid nights are currently less expensive in many destinations due to decreased travel demand and low occupancy. Programs like Hilton Honors and IHG Rewards that offer dynamically priced awards generally provide better value awards right now than programs like World of Hyatt and Marriott Bonvoy that use award charts.

So you can currently book most Hilton hotels for far fewer points than usual – at least for the type of Hilton hotels I typically search for and consider booking. I've found more opportunities to redeem Hilton points for greater than 0.6 cents each than I did pre-pandemic.

Plus, award night reservations are almost always fully refundable as long as you cancel within a few days of check-in. So, you can snag a good award rate now for trips you hope to take later this year and in early 2022. Then, periodically check your reservations for rate drops. By checking for rate drops, I recently saved 18,000 points by rebooking two Hilton stays.

Related: 6 reasons why now is the time to book travel with points and miles

3 Hilton Honors redemptions I've booked

My husband JT and I didn't stay with Hilton Honors frequently during our first years living as global digital nomads. And we're currently traveling domestically by RV during the pandemic. But once it becomes responsible, safe and relatively easy to globetrot again, we'll return to living out of hotels as digital nomads.

We plan to stay with more Hilton Honors properties once we're on the road again. In particular, I've already booked the following five-night Hilton Honors award stays (to maximize the fifth night free on awards perk for Hilton Honors elites):

• DoubleTree by Hilton Hotel Cape Town - Upper Eastside in September
• Our reservation: 52,000 points (worth $312 based on TPG's valuations)
• Current points cost: 60,000 points
• Current best flexible rate: $388
• Cents per point: 0.75
• Anselmo Buenos Aires, Curio Collection by Hilton in October
• Our reservation: 84,000 points (worth $504)
• Current points cost: 84,000 points
• Current best flexible rate: $576
• Cents per point: 0.69
• DoubleTree by Hilton Hotel Cape Town - Upper Eastside in January 2022
• Our reservation: 48,000 points (worth $288)
• Current points cost: 48,000 points
• Best flexible rate: $322
• Cents per point: 0.67

Some of these stays may need to be canceled or delayed. And I'll rebook stays if a lower points cost or a lucrative paid option appears. But I appreciate having these redemptions locked in, as we'll have these bookings even if prices rise.

Related: Choosing the best Hilton credit card for you

6 other Hilton Honors redemptions I'm considering

Frankly, I would book several other Hilton Honors award stays if we had the Hilton points. However, JT's Hilton Honors balance is close to depleted after booking the above stays. We could buy more Hilton points during a 100% bonus sale to boost his balance. But, due to travel uncertainty and flexible paid rates, we're holding off on buying points for now.

While writing this article, I went through our upcoming travel plans and priced out paid and award stays. I considered Hilton properties at every destination where we'd spend five nights or more since we can typically get the best value from Hilton points when we get a fifth night free. However, I excluded destinations where we'd likely stay with another hotel loyalty program. And I excluded redemptions that provide less than 0.64 cents per Hilton point of value.

In doing so, I found the following six Hilton properties at which I'd consider booking five-night Hilton awards if we had more Hilton points:

• Hilton Belgrade in June
• Points cost: 104,000 points (worth $624 based on TPG's valuations)
• Best flexible rate: $690
• Cents per point: 0.66
• Why I like it: This hotel is well located in Belgrade, Serbia, which is a city I've wanted to visit again. Plus, this Hilton has an executive lounge, which we'd get to access thanks to JT's Hilton Diamond status.
• Conrad Cairo in June
• Points cost: 68,000 points (worth $408)
• Best flexible rate: $438
• Cents per point: 0.64
• Why I like it: Staying at a Conrad, which has an executive lounge, for less than 14,000 points per night is pretty incredible. Plus, all of the rooms offer at least a partial Nile view.
• Hilton Dusseldorf in June
• Points cost: 88,000 points (worth $528)
• Best flexible rate: $581
• Cents per point: 0.66
• Why I like it: Dusseldorf is an underrated German city that I've been meaning to spend more time exploring. This Hilton, which has an executive lounge, is located halfway between the airport and city center.
• DoubleTree by Hilton Zagreb in June
• Points cost: 100,000 points (worth $600)
• Best flexible rate: $656
• Cents per point: 0.66
• Why I like it: I still haven't visited Croatia and this DoubleTree would be a good base from which to explore Zagreb.
• Millennium Hilton New York One UN Plaza in August
• Points cost: 114,000 points (worth $684)
• Best flexible rate: $774
• Cents per point: 0.68
• Why I like it: This hotel has a 30th-floor executive lounge and is a relatively low-cost redemption for staying in Manhattan in the summertime.
• Hampton Inn & Suites Mexico City - Centro Historico in January 2022
• Points cost: 76,000 points (worth $456)
• Best flexible rate: $506
• Cents per point: 0.67
• Why I like it: This Hampton Inn is just a few blocks from Mexico City's Zocalo. I stayed in this neighborhood on my last visit to Mexico City almost nine years ago, so I'm eager to return and see how much it has changed.

Despite Hilton's dynamic pricing, I expected to see more redemption value variance in my top picks. However, this exercise showed me that I should focus on Hilton Honors awards that provide 0.67 cents per point or higher. I'd almost certainly get a higher redemption value by redeeming for select high-end properties or redeeming for premium rooms. But I prefer to stretch my Hilton points for more nights at inexpensive properties.

Related: 20 of the best Hilton hotels in the US bookable for 20K points or less per night

Bottom line

If you have a stash of Hilton Honors points, consider redeeming your points for one or more upcoming stays. By doing so, you can lock in current award pricing. And, if the award rate drops or you find a better option, you can usually cancel and rebook.

It may also be useful to price out several upcoming stays even if you don't have enough points to book every stay. By doing so, you'll see what type of redemption value you should aim for when redeeming Hilton Honors points. After all, your target redemption value may be higher or lower than mine based on your redemption style, how many Hilton points you have and how easily you can earn more Hilton points.