April 10, 2026
Reader Success Story: Hilton Waikoloa Village
Pam
Tiffany sent us her reader success story about using points and miles to stay at the Hilton Waikoloa Village on the Big Island. Here is her story:
My best travel on points to date….
In April 2025, my husband and I stayed at the Hilton Waikoloa Village for five nights, all on points. We used 305k Hilton Honors points and got the fifth night free, including the resort fee and other taxes. As Hilton Honors™ Gold members, we received an $18 daily dining credit each.
Both my husband and I have two Hilton Honors American Express Business Cards, and he also has the American Express Hilton Honors Aspire. We had $290 in quarterly Hilton credits to use, and we checked out using all five cards to get them. We enjoyed a morning latte and a small treat from the coffee shop, which used our dining credit daily.
The resort food was spendy, and the two meals we had at the resort just weren’t worth that price. We used the market just a five-minute drive away (and the resort has a shuttle that stops there, as well). The market has deli-style food and a well-stocked, reasonably priced grocery store. We rented a cabana a few of the days, and also rented a car for one day to explore the island.
We both flew round-trip from Kalispell, Montana, using approximately 156k Chase Ultimate Rewards®, as my husband uses a Chase business card for all his business expenses. After our dining credits, quarterly credits, points to cover the room, and Ultimate Rewards® points flying us round-trip, we checked out for just under $300, which was the only cost of the trip.
Our Next Trip
The resort was amazing, and we booked another family trip for nine for February 2026—four rooms, all on points, and Chase Ultimate Rewards® flying us all round-trip. We’ve booked four rooms at 305k points each, totaling 1,220,000 Hilton Honors points, all earned with the Amex Hilton Honors Business cards and the American Express Hilton Honors Aspire. We also booked nine round-trip flights in total: eight from Kalispell, MT, and one from Missoula, MT, for a total of 733k Chase points from the Chase business cards.
I started using points and miles in 2023 after listening to your podcast, and I became obsessed. My husband and I take about one trip per month now that we know how to use our points and expenses (our goal is 12 trips in 12 months), and it’s allllll thanks to you and this amazing group.
Thanks, Tiffany, for your trip report—we are so glad that you are finding our information useful!
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