Best Tools for Booking Hotels with Points & Miles with Greg the Frequent Miler
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Hello and welcome to All The Hacks, a show about upgrading your life, money, and travel. I'm your host, Chris Hutchins, and today we have a bonus episode that's really part two of my conversation on Wednesday, where Greg, the frequent miler, and I did a rundown of all the different tools that exist to help you book amazing flights with your points and miles. Today, we're going to do a similar deep dive on all the tools for hotel booking, so you can book the best stays on trips as well.

Also, since we recorded this, one more hotel search tool has launched. So I'll make sure to cover that at the end of the episode. But for now, let's jump into all the best award tools for hotels right after this.

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The first way is basically what I think everyone would assume a hotel award search tool would do, which is basically you're planning a trip and you want to say, I'm going to London. I'm going from July 1st to the 6th. Show me what hotels are available. How much do they cost in points? That's what you would expect any good hotel award search to be able to do.

And surprisingly, there's only one that I'm aware of that's currently available and does it well enough for me to talk about. I know of one that's sort of in development and I've looked at some others that are kind of these half-baked tools, but they're just not even worth talking about. So the one that's available is called Aways with a Z at the end. And that does all the things I was just saying.

One of the cool things about it, it searches a lot of hotel programs. So it checks the boxes for the major ones like Marriott, Hilton, Hyatt and IHG. But it also includes Accor, Choice and Wyndham. And my understanding is they're adding more. So that's really nice. I'm doing a search right now for Paris and Accor has so...

has so many hotels in France that it's almost overwhelming. Even if I just filter that out, the map is pretty full. And if you zoom in, there are a lot of options. I just think it's funny that there's three or four other tools that we could talk about, but none of them actually do this thing, which is what most people listening probably want, which is, I'm going to Paris from the 12th to the 16th of April. Where can I stay? And is it a good deal?

Years ago, there was a tool called a word mapper that did something similar, but that's no longer available. So finally, with a ways, there's a tool that does this thing that should be an obvious thing that a lot of people do, but no one else currently doing it.

It lets you do things like search by star rating so you could find the best hotels. You could sort by the cost in points or the cost in cash. It'll show you a best value indicator next to each hotel. You can now sort by that, actually. I just noticed that the sort includes point value. Yes, so that you'll get the best use of your points sorting to the top, which is great. And then if you click into a hotel, you can view a award availability calendar.

Maybe your dates for your trip aren't totally set or maybe the hotel you were interested in wasn't available for the whole set of dates and you want to see which days is it available. You could use their award availability calendar, which is really neat.

I've used Aways for almost every trip when it comes to searching for cities and award hotels. We actually just did a session where the founder of Aways for the AllHacks members did a full product walkthrough. We got to ask questions, one of which was like, they used to roll out city by city. So we said, "What kind of coverage do you have now?" And the answer now is all. We asked like, "When will you have all the hotels for all the programs?" And they're like, "We do."

And so I think one of the earlier things was they might have only had 100 cities to start, but they've loaded in all the cities for all the programs. And you just get, I think, one of the best views of I want to use points on these days in this place.

The only thing missing might be some flexibility. If you were like, I'm going to Paris for a week, kind of be a little flexible, but you're not necessarily set on a specific hotel. I think that's one thing you can't do when it comes to doing that kind of search. It's really great. Totally agree. The guy who started the company...

met with me a while back to talk me through the app and show me what you could do. And for a few trips that I had planned, I tried to use it. But each time I tried to use it, the city I was going to wasn't available in the tool. And so I gave up until recently. Then I looked at it recently. I was like, oh, wow, everything is here. And so suddenly, you know, magically, it's really good. I will say I've run into a few cases where I've

It uses cache results that were out of date or for some other reason it was wrong. One where it was just flat out wrong with the points that it said it costed. I sent them an example, and so they're going to work on that and try to figure out what's going on. I just want to point out it's not perfect, but...

It is very good, I think, in doing what it's intended to do. And since it's the only thing out there that does exactly that, it's an easy answer. Yep. I will say I just pulled up rooms.arrow. And unlike all of the other seats.arrow functionality, their hotel search function

Works a little bit more visual than data organized. Yeah. And so I did the same search for Paris. It's designed for a little bit more flexibility. It's like what range of check-in dates, how many nights do you want to stay? And it shows me less hotels than a ways because I think they're only searching Hilton, Hyatt, and IHG. So there's noticeably Marriott is missing from that list as is...

Wyndham or Choice Hotels or Accor. But it does have better than I thought ability. That said, it immediately popped up and said it's refreshing stale results. It knew it had stale results, quite a bit of them, but it's refreshing them. But you can't sort by anything. So the number one result is...

the Holiday Inn, and the number two result is the Park Hyatt, of which I would say those are two very different hotels. Yeah. It kind of does it. But again, I think a Waze is the only tool you can rely on for that kind of search. Right. Also, you mentioned that it supports IHG, Hyatt, and Hilton, but it's important to note it does not include all IHG hotels, all Hyatt hotels, all Hilton hotels, not by a long shot. It has a database of ones that it...

looks at and that's all it does. So searching Paris, it probably hit the core of where a lot of people are looking. But if I search to a more obscure place, it probably wouldn't work. Try Lexington, Kentucky. I bet you'll find like one hotel or something. One hotel. All right. So that's the basics of

aways and hotel trip planning. One thing that we didn't mention when talking about aways is that you can also set alerts. So if you found a hotel that you want to stay at, it's not available, you can set

set up an alert to email you when it becomes available. With hotels, even more than flights is availability does change a lot, even more than flights do, partially because I think a lot of people book hotels with free cancellations and do cancel. As you have cancellations, the word inventory automatically goes in and then you can book it.

So that's a really nice feature. It gets us to the other category of hotel tools. If you're not doing planning for a specific trip, but rather have like a hotel in mind that I want to stay at this hotel, but I'm having trouble finding award availability. That's where there's a whole host of tools that try to help you with that. Some of them started because...

Hyatt does not have an award availability calendar. Unlike Marriott and Hilton and even IHG, you could bring up one if you know how, there's no way with Hyatt by itself to see for a given hotel which days can

Can I use points? It'll tell you how much it'll cost in points if it's available, but not whether or not it's available. So these tools grew up to be able to answer that question and more. The first thing that most of these tools offer is a full year calendar of award availability. And so we saw Waze has that available.

But there's a bunch of other tools that have that as well. And so I looked at Award Tool has a hotels feature. I looked at that. I looked at rooms.arrow, which we were just looking at as well. I looked at Max My Point and Stay With Points. As you're saying this, I'm playing with these tools and searching for a few different hotels. And it's just funny because

how some of them have very different ways to express a hotel. I'm looking at one of the properties near me, which is notably hard to stay at, which is the Alila Ventana Big Sur. And I'm laughing because AwardTool says 66% available. Meaning, according to them, 66% of the dates have availability. StayWithPoint says 0% available.

Yet when I click on it, even though it says 0%, it has lots of dates that show availability. I know that's one example of a place people are often trying to find a dream stay at. But I'm curious whether you think some of these tools have better coverage because I don't do a lot of hotel searching, but my wife was looking to book a stay at the Miraval, which is a pretty good Hyatt Redemption in terms of cents per point. It is a lot of points...

But for those points, you end up getting an all-inclusive high-end resort. They even throw in $175 per person per day of resort credit when you book with points. Right. But it wasn't available on every platform. So is one of these tools better for coverage? Yeah. I mean, Waze has by far the best coverage because it has all hotels, but it doesn't do some of the

key things we're going to talk about in a moment. Of the tools that do more advanced stuff for finding availability, MaxMyPoint, in my opinion, seems to have the best coverage. I would just completely skip over this availability percentage. I don't know if you got value out of it. But if you're looking on video now or if you just want to hear my voiceover, they say the percentage of reward nights available to book in the following 365 days is

And I'm clicking through and in April, it's almost every day. In May, it's almost every day. And in June, it's a handful. It seems like it is available. Now, what I think it's saying is percentage of reward nights available to book with a standard priced award. It doesn't say that unless that's what it's trying to say. I don't understand how they're calculating it, but...

You did more research than me. It's funny you called that out because that's something I noticed early on and I just stopped looking at it. So I haven't tried to figure out which tool gives a close to accurate answer on that. I just haven't looked at that. Let's talk about some of these things that tools can do. We talked about that they can all be used to look at a full year of award availability. They're all using cached data, so they're all wrong to some extent.

The best ones show you when it was last updated so you could at least know, is this reasonably good data or not? They all let you set alerts to find out when the room becomes available, but that's where they vary a lot because

Because some of them, like a Waze, you have to set a specific date range, either that hotel's available in that date range or not. But what if you just want to be alerted anytime across a whole year that there are new awards available at this hotel? Max My Point can do that. Or what if you want to know, alert me anytime there's

five days in a row available in December at this Maldives resort or whatever. Stay with points can do that. So they have different like advanced alerting features that can be really important in different situations. Okay. So do you have a favorite?

Yeah, the Max My Point seems to check most of the boxes pretty well for this kind of advanced searching, the ability to find these hard to get awards at places like Alila Ventana. Max My Point, it supports all four of the major programs, Hilton, Hyatt, IHG and Marriott.

And just to give you an example, like rooms.aero doesn't support Marriott and stay with points doesn't support IHG. MaxMyPoint also will let you set alerts to alert you if the price drops.

So let's say you've booked an IHG awards day. IHG award prices change all the time. You'd want to know if the price goes down and be able to rebook it then for the lower price. So you could set up a Max My Point to let you know when that IHG hotel has dropped in price from whatever you booked. You just have to put in that total. It also has a really good filtering features on its homepage.

Let's say you've got some of those Hilton free night certificates that are good at any Hilton worldwide. So what you want to do is stay at one of these like really hard to get Hilton properties like the Waldorf Astoria in the Maldives or the

Waldorf Astoria in Los Cabos. Those are really hard to find. You can use alert features to let you know when they're available. But if what you're trying to do is just find the best hotels that are bookable with Hilton points, you could use Max My Points homepage and

and filter to Hilton, filter to properties costing, let's say, between 100 and 150,000 points, which would get you to their top end hotels. And then you'll see you can sort by like most popular and you'll quickly see some that you might want to target.

I do not have a paid membership for Max My Point, which I want only because it is the only one of these sites that has ads all over it. And I would love to make them go away. So that's my next investment is a Max My Point membership. You know, it's funny. When I first looked at Max My Point, the free version, it had way more ads than it does today. It was almost unusable. It had so many ads.

And they were constantly covering out what I was trying to do. Today, yeah, it still has a lot of annoying ads, not nearly as many as before. I didn't mention that, but that is true. And the free version, if you could stay on the ads, it's fairly capable. But the paid version might be worth it if you do a lot of this kind of thing. And we didn't talk much about the hotel tool from AwardTool. Where does that fit in? It's sort of middle of the pack, in my opinion. It has some decent features, but it didn't...

beat out Max My Point on any of the types of things I looked at. I guess the way I think about it, if you're using Award Tool anyway for flight searches, you might as well check whether it can do what you want with hotels as well because you're in there anyway. But if it can't, then go on to another tool like Max My Point. And I think you probably have gone deeper down the hotel search Award Tool rabbit hole for hotels than I've kind of done a lot in flights.

hotels, I'm kind of like, I'm going to find my flight and then I'm going to just kind of see what's available at these hotels and make it work either way. Especially when you have cool things nearby that you can drive to or if you have a lot of flexibility in your travel, I feel like I'm underusing the hotel tools. So personally, I'm excited because this episode made me understand that there's more I can be doing. I love Lila Ventana, Big Sur. And if I was in driving distance like you are...

The Max My Point has these daily alerts, which you have to have the paid version to do it. Every time a word availability changed at all, it'll send you an email saying, here's all the dates that's available. And then I would scan it each morning and say, oh, there's a date that I might want to go. Let's go ahead and book it. Of course, you can cancel if you change your mind.

The idea that we live less than two hours away, work from home and could go on a weekday and still haven't been to Ventana is a little crazy for me to think about. Maybe that'll be on the 2024 before the end of the year. Let's tick that box. Well, of course, you have kids and Ventana is adults only. So maybe that's a getaway for you too. And I need to set up a Gmail filter that forwards the Ventana alert availabilities to my parents.

and just say, hey, if any of the dates align and you want to come down and hang out with the kids for a couple of days, if they're listening, maybe this is too much of an offer. I'll book four nights. We'll take them for two. And then you can go down and take the other two nights as an exchange for watching the kids. So is there a hotel that in the Bay Area that you've been to and you'd recommend it's worth watching the word availability for that one? I don't think I've stayed at a Bay Area hotel.

in a very long time. - I guess that makes sense. You have a house. - Yeah, we live here. The one that I've heard a lot about, which I have not stayed at, but I've heard great things about the Alila in Napa for people looking to do a little escape to wine country. I have stayed at the Westin Verasa in Napa. I wouldn't say it's a hotel I would plan an entire vacation around,

But I would say if you're in Napa and you don't want to go for something wild, it's a great hotel. I'm sure the Alila is probably nicer, but it suited every need we had when we were there before my parents moved to Napa and we can stay with them. Let me talk about a special use case that I mentioned briefly, but there's a hotel in Michigan that I really like going to called the Anna Bay Harbor. It's a Marriott hotel, of course, very popular in the summertime because it's

very cold other times. And it's right on Lake Michigan. It's beautiful. Award availability in the summer is very hard to find. They don't show one night award availability. So if you're looking just one night at a time, you're not going to see anything. If you use Marriott's flexible dates calendar and just say, I want to look for one night, it's not going to show any availability. But if you look for two nights, then things might show up if there's anything there. But most of the time, there's nothing there. So there's two ways to

of handling that. One is stay with points. We'll let you create an alert that says, show me any time for the month of June or the month of July when there's two nights available, any time in the whole month. That's one way. The other way, what I did this year, is I use max my points any day alert. And...

It's any day alert won't tell me when there's summer availability. What it does tell me is when a lot of things have changed with availability at this Marriott. So I'll see a flood of nights all of a sudden open up in the spring. And so then I jump on a Marriott's website and do a flexible date search in the summer of two or more days. And then I've been able to find

awards that way. So it sort of triggers me to look on Marriott's website when it's time. That would be a great example of a place that you keep an eye on. Any other hotels that you thought were just such amazing properties and good deals for the points that if people were looking to get inspired, where should they go explore some of these special kind of impossible to find hotel awards?

Yeah, a few come to my mind, but there are SLH properties, which are no longer bookable through Hyatt, but they should become available through Hilton soon. So maybe it'll still be relevant. Hilton has taken over a partnership with SLH that Hyatt used to have. Most notable that I can think of are in Queenstown, New Zealand. There are

two amazing properties. I stayed at one of them, but I've seen videos of the other one. And the one I stayed at was just amazing. It's right on the lake. The base rooms are huge suites. Breakfast is included and it's incredible. They have a evening cocktail hour where you come in and there's like a host there.

who asks you what you want to drink, prepares your drinks, and then asks you if you have any dietary restrictions and then goes and tells the chef that we're ready for the chef to prepare our canapes.

And so the chef then custom creates some snacks, basically, while we're enjoying the complimentary drinks. Very special hotel and probably the most unbelievable location in Queenstown, New Zealand that you can get. So that would be a great one.

We've stayed at the Conrad and the St. Regis in Bora Bora. And because San Francisco has direct flights to Tahiti, it's like just such an easy place to get to. The difference between getting a room for a good deal on points and paying full price can like triple the cost.

I've done an episode I'll link to in the show notes about going to Bora Bora. But if you can find a time where United has saver business availability, you can book with Aeroplan and the St. Regis has pretty affordable deals or the Conrad does, all of a sudden you're going on a $30,000 trip for a fraction of that. If you pick a different week, you might be going on a $30,000 trip for $30,000, which is not a trip I'm excited to go on.

I think if you can time the flight and hotel award availability to Bora Bora, you can go on a just an incredible trip that's less than eight hours plus a short 30 minute flight from the West Coast that they can't be beat. Yeah, no, it's interesting. There are certain hotels like this where it's probably worth planning your trip around the hotel availability, where

Whereas there are many trips, like if you're going to a big city, you might want to plan the trip around the flight award availability because you know you're going to be able to stay somewhere nice. There's so many options. But when going to Bora Bora, the Maldives, places like that, you might want to find the resort first and then book your flights. We've never done the Maldives only because...

It's just so far away. And I don't know how... I'm sure someone will send me an email and tell me how much better it is than Bora Bora. But for being three times farther away and not even close to a direct flight for the majority of the long haul, for me, it's like, wow, it's just not even worth it.

But the crazy thing about Tahiti is that because you can time it, if you take two different airlines, you can't take the same airline and make this true. Right. But you can take day trips for both of them. An eight hour flight during the day in economy is pretty doable. It's a couple hours longer than going to the East Coast. If you're used to using your miles and points to splurge on business, I

I'm not even sure it's necessary. Now, if you have enough points, why not? Whereas to go to the Maldives, I think the experience of flying eight hours to Tahiti in coach is not probably the same as flying to the Maldives almost 24 hours. I don't know, 10 years ago with no kids.

you could have put me in the middle seat in the back of the plane. I would have been fine to go either places. Once you played the points game long enough, you're like, well, there's gotta be a way I can do it for a better deal. Yeah. I think you're getting at a point here, which is like, if you're gonna be traveling with four people and if you're looking at places that are really far away, then the flight availability almost has to be

more of the driver than the resort or hotel or availability. For me, usually traveling just my wife, I know I can find something in business class to just about anywhere. I might have to make a positioning flight or two to make it happen, but I can usually find something. And I think just for anyone listening who's maybe new to the Points and Miles world, I

I always think it's funny that when I talk about looking for flights to places, I'm always like, "Well, I couldn't find business class, so we're going to find another date." Just to be clear, I don't think I've ever spent the $5,000 to $20,000 those business class flights take. This is not me speaking out of a desire to spend on that level of luxury.

It's just that if you figure out how to use these tools, if you figure out how to time the card bonuses and your spend and all the other stuff that you talk about on your show and I've talked about on my show, you end up getting to a point that you're somewhat spoiled to the fact that you can find a way to do it in a premium cabin at a very reasonable price almost every time. Exactly. It lets you do things like this routinely. Yeah.

that you would have never even considered forking out the cash to do. Things like staying at these resorts that cost like $2,000 a night. Several of the ones we mentioned before, we didn't talk about the prices, but would be in that range. Or flying business class for, as you said, anywhere from $5,000 to $20,000.

Those are not things I would consider paying cash for, but points makes all those things accessible. And so that's what I love about it. And we do become spoiled. I laugh at my wife when we flew Air France business class. It was kind of an older plane. It was fully lie flat, direct aisle access. And she's like complaining about how it wasn't as nice as the previous flight we were on. And I just love that we could be that spoiled. We complain about it even though it's still...

Incredible luxury. And still not have to pay anywhere near full freight, which is great. This trip to Miraval was just a two-night stay,

the rack rate for the same dates was over $6,000 for two nights, which is like, it wouldn't even be an option. Like we would just never do a trip like that. And unfortunately on this trip, I'm not actually going. My wife is going with a friend of hers to celebrate a birthday. And so I'm going to have her join on the show sometime after she stays in April to give a little rundown of how that trip was and she can share with everyone. But the only other thing I wanted to mention before we wrap is that

On hotels, if you are not finding what you want, but you are still looking for a little bit of a perk or a benefit in the luxury travel world, there are a lot of different ways that you can book a hotel and add on a lot of different perks. Anyone with an Amex knows that Amex has the Fine Hotels and Resorts program. Chase and Capital One have all launched those. We launched our own

at hotels.allthehacks.com where you can search for the higher end four or five star hotels and get access to perks like free...

breakfast, resort credit, free upgrades, early check-in, late checkout. I would encourage everyone to figure out how to use their points and miles. Use everything we talked about in this episode to get your stay for free and get all kinds of stuff. But if you end up spending dollars and you are staying at a nice higher-end hotel and you have to pay for it, chances are...

through one of these platforms, you can get a pretty awesome set of perks added on for the same as the rate you typically pay at the website. It might not be the same as the discounted corporate rate you have through your employer or a last-minute hotel tonight rate. Basically, we found a partner that would help us give everyone access to... I think it's 4,000 hotels. Chase and Capital One might have 1,000. Amex has 2 or 3 and we have 4,000. I

I think we have a bigger selection of them, but you can get all those same perks if you want. So sweet. And is there any fee to use that service? There's no fee. You can book it. You can cancel your awards. I will say to provide this, we had to make some UI sacrifices. So the tool that you'd use is not the easiest to use.

If you go to allthehacks.com slash upgrade, I'll put a video if people want help walking through the tool. Greg, because you dive into this stuff way deeper than we do. Where can people find what you're reading, writing and talking about on your show? Yeah. So start at frequentmiler.com. That's where you'll find our blog and links to our podcast, which is called Frequent Miler on the Air. You'll just find a wealth of information. We have resource guides about all these things. We have the best...

list of credit card offers on the internet. Unlike most other websites, we only post the best offer that we know about for the reader.

And we don't list offers that are inferior. For example, there might be a 120,000 point Amex Platinum offer that is available on most websites. But if you go to our website right now, you'll find 150,000 point offer listed there. We don't earn anything from you clicking through that offer, but...

We think it's the right thing to do to show the offer that gets people the most points rather than what would pay us. So that's a big deal. Tons of different resources about how to earn points, how to use them, shortcuts to elite status, things that Chris talks about all the time, but you might get more in-depth on the blog there. Greg's underselling it. There is so much good stuff. Your podcast is one of the few that I listen to every time an episode comes out because...

I love going deep on this stuff. It gives me so much inspiration for ideas to talk about and podcasts to do with you and Nick, and we'll see where it goes from there. So definitely check out the podcast, the website, reach out to either one of us if you have questions. Absolutely. All right. Thanks so much. Thank you, Chris.

Thank you so much for joining us for this bonus episode. I hope it helps you get the most value out of your points when it comes to hotels, and it makes it much easier to find the best deals. I have links in the show notes and at allthehacks.com to all the tools we covered, including some great deals on a few of them. And since recording, Points Yeah actually launched a hotel feature on their site.

which includes searching all five major hotel programs, Hilton, Hyatt, Marriott, IHG, and Wyndham. It also includes support for looking at Hyatt, IHG, and Marriott free night certificates. And it shows the cash rates from all the different portals Amex, Chase, Capital One, Citi built, as well as some rates booking from American and United portals and rates for Amex, Fine Hotel and Resorts and Virtuoso.

Fortunately, it looks like most of these features are free. I can't quite tell because I have a paid account and you can't use them unless you create a free account and log in. However, unfortunately, the hotel search tool does not include a calendar view for individual hotels. So if you're trying to plan a trip around availability at a very specific property, this probably isn't the right tool. But if you're already planning to go to a city like Paris or London or Tokyo, and you're just looking for the best hotel deals in that city to use your points on,

Seems like this tool could be a great option. So that's my recap of points. Yeah, definitely check it out. Also check out our YouTube channel, allthehacks.com. If you want to watch the video version of this episode where I shared my screen. And finally, make sure to check out Frequent Miler on the Air, Greg's podcast, if you want to go deeper on all things points and miles. Thank you so much for joining me today. Podcast at allthehacks.com. If you want to reach out, I will see you next week.