Travel Planning: Where to Stay

Besides airfare, hotels are likely the biggest expense on your trip. It’s also one of the riskiest, because a bad night’s sleep can ruin your vacation. However, travel styles vary greatly and so do your options. So how do you get a good deal and still get the kind of accommodations that are best suited to you? 

Before you proceed, I have a caveat: this is only for the casual traveler who hasn’t built up loyalty with a specific chain. I’ve found that for the traveling that we do (only about a month total in a year, and in various areas all over the world), sticking to a chain isn’t really worth it, but for the business traveler, that might be a better way to go

This is my usual process for booking hotels. Once I’ve decided on a location and some dates, I check out hotel prices in the area to get an idea of cost. Then, I shop around on my favorite sites to see if there’s a good deal to be had, and then I commit to the one I like best. So, for example, David and I are itching for another Maui trip, and we’re looking at a weekend in May.

1. Hotels.com

Map view on hotels.com. Not a lot of options in Maui in May for my price.

Map view on hotels.com. Not a lot of options in Maui in May for my price.

Hotels.com is my go-to first site, because they have a straightforward rewards program. If you book ten nights, they’ll take the average and you get that amount to use for a future stay. Your free nights never expire.

So if you booked three nights at $100, two nights at $70 and five nights at $120, you would have one night worth $104. Note that if you choose to use that amount for a hotel that is worth less ($95, for example), you don’t get the difference back. You can, however, use it towards a hotel that is worth more ($105 and up), and then pay the difference. Also, taxes do not count toward your average, only the base amount for the room.

I like to search by map view, so that I know exactly where my hotel is going to be. I also like the filters — Maui is an expensive place to go, and I have a budget so I know I’m not gonna bother with hotels that are too pricey.

Once I find a potential hotel, I read the reviews on both hotels.com and TripAdvisor so I know what to expect. I also like this option because I can book refundable in case I change my mind.

If you like to know where you’re staying, and you like hotels or condos, you can stop right here. I’d also stop here if I’m going to certain areas where the below options won’t work due to limited options (for example, Siem Reap, Cambodia). But if you’re a little more daring, read on for other hacks.

2. Priceline or Hotwire

Also not a lot of Express Deals available for Maui in May. This is going to be tough.

Also not a lot of Express Deals available for Maui in May. This is going to be tough.

Next I go on Priceline or Hotwire. These sites will give you deals, but they come with a little risk: you won’t know your hotel until you’ve booked it, and it’s completely non-refundable. On Priceline, there are two ways of doing this, Express Deals or Name Your Own Price. The only difference between the two is that Express Deals lets you choose from a pre-determined list, whereas Name Your Own Price is a bidding process. On Hotwire, you just have a list of options, no bidding.

On both sites, you are shown the price, the area, and the amenities.

The risk can be scary, but keep this in mind: you can choose your hotel’s star rating, and there are websites that will help you. My favorite is BiddingTraveler, where you can look up your area and see exactly what hotels have been won for what price. They’ll also advise you on a bidding strategy if that’s the way you want to go.

I like doing this for areas that I know aren’t too risky, like Berlin or San Francisco. If I’m short on time, I won’t bid, otherwise I’ll make the effort. I got an $80 4-star hotel in Brussels this way (which would’ve been over $200 if booked directly with the hotel).

If I’m not ready to commit, I go to…

3. Airbnb or VRBO

Below $100, now we're talking! Time to read some reviews.

Below $100, now we’re talking! Time to read some reviews.

This is a new discovery for us, but this will be more of how we travel in the future, I think. Airbnb and VRBO are like renting someone’s room or house for the night. The quality varies greatly and so do the prices. Some selection savvy and a little trust is required for this method, but the payoffs are, I think, worth it. You just have to read the reviews, look at the photos, and ask questions.

People unfamiliar with the idea seem freaked out by this option. Someone said half-jokingly, “That’s how you die.” I don’t think safety is of particular concern though, and I love that Airbnb asks you to rate your host– and that they can rate you. And more and more people are liking the idea of renting out their extra space. I have a friend who has been going through a series of roommates, and is now deciding to convert to Airbnb. It’s more lucrative, you meet different people, and you don’t have to have someone around all the time if you suddenly need the space (like if you have family coming to visit or something).

We particularly enjoyed the personalized experience. You’re basically a guest in someone’s home, even if they are a stranger. On our recent trip to Europe, we stayed with some great people who took really good care of the spaces they rented out, and sometimes went above and beyond for us. One picked us up from the train station. Another offered us transit cards to use while in the Netherlands. And the room we rented in Amsterdam was absolutely beautiful. A comparable hotel room in Amsterdam would have cost us over $150. With Airbnb, you don’t get turn-down service and you probably won’t get your towels changed every day, but do you really need all that?

4. Groupon and other travel deal sites

This is a less common option for me, but one that I use on a per-location basis. For example, Groupon usually has good deals for Las Vegas if you know your dates. We also used a local deal site to book a hotel in Boracay, Philippines, because most of the accommodations on the island were not on hotel sites.


In general, my suggestion is to check out all these options until you find the price and place that is right for you. It’s a bit of work, and it’s not foolproof, but it works for us. Do you have other tricks for getting good deals on accommodations? Drop me a note below! And for more helpful ideas, head on over to my Travel Tips page!

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