I am looking to use hotel points for 1 or 2 nights in Anchorage this summer, when rates are high. Both the Hilton and Marriott have a large hotel at about $300 per night in a convenient location and the two hotels seem comparable in quality, but in points, Hilton requires 40000 and Marriott 25000. I have more than enough points for either, although more Hilton points. Which are a better use of my points? In other words, are Hilton points worth less than a Marriott point? I am only silver in both chains, so no special elite benefits expected. Thank you.

Are the hotels of similar quality and do they have similar customer satisfaction levels? I would check that first.

After that, this is a difficult question for me, too. The number of miles mean practically nothing. One thing you can do is look at converting the points to a similar airline. For example, 10k Marriott points will get you 2k AA miles, but 10k Hilton Points will only get 1.5k AA miles. So that suggests that Hilton points are roughly worth 75% of Marriott points, but that is a very rough estimate. The Marriott is a slightly better value than the Hilton using those estimates.

But converting to airline miles is rarely a good use of hotel points. A better question is, what else can I do with the miles? Based on where you travel, the types of hotels you like, and your remaining balances/ability to earn more points at those chains, which miles are you more likely to use in the future?

For example, if you rarely stay at Hilton hotels and you have exactly 40k Hilton points, use those. But if you have 50k Hilton points, and use 40k, it will be pretty hard to use the 10k remaining points for hotel nights, unless you like Hampton Inns in rural or industrial areas. If you have 125k Hilton points, those are much more valuable used on a 4-night VIP or AXON award, so to break them up into 40k and 85k chunks really decreases their value.

I don't know enough about Marriott to give you any pointers there, so maybe someone else can jump in here...

I use both Hilton and Marriott and to me, Marriott points are definitely more valuable, but Hilton points are much easier to earn...especially if you get points from credit card spending. As a rough estimate, I value Marriott points at about 1c-1.5c per point and Hilton points about .33c-.5c per point, but I really look more at how much credit card spending it costs me to get a free room. In your example for the Marriott, it would cost me $25,000 of regular spending or $12,500 of restaurant spending (2 points per dollar) for the 25,000 point room. Since I only use my Marriott card for restaurant spending, let's say $12,500. With Hilton for 40,000 points, I would use $6667 of spending (6 points per dollar for grocery and various other bills). So to me, the Marriott points are about twice as valuable as the Hilton points in this case. So if the quality and other features of the hotels are similar, I would say the Hilton for 40k points is the better deal.

+1 on Marriott points.

You might want to check into additional costs (since you're only Silver) of things you might use, like internet and breakfast and parking. If those are much higher at one of the hotels than the other, that could be another factor.

If all is really equal, I'd stay the difference in value between Hilton and Marriott points is not great enough to necessarily cover the difference between 40k and 25k. So on purely that aspect, I'd say the Marriot 25k is a better value than the Hilton 40k.

(You might want to check whether Hilton has a cash+points rate there, though. That could cut the points in half to 20k, perhaps, while adding only a relatively small $$ cash component. And if you book by tomorrow (Jan 31) after having registered for the Get Points Back promo (or it's called something similar), then you'd get 33% of your points back after the stay. (But that promo only applies to cash + points, not regular points-only reservations.)

But all is often not equal. How do you replenish these points? If it's much easier for you to replenish one or the other, that could alter the balance of value for you.