You’ve decided where to go- now how to book accommodation?

how to book accommodation in Tuscany

Okay, you’ve decided on your travel destination. You’ve determined your itinerary. Now you need to decide where to sleep: How to book your accommodation? I get asked this all the time, and I know the process can feel overwhelming. Here are my simple steps to take on the giant task of how to book where to sleep so you can figure it out in just a few hours. Of course, if it’s still stressful, just use one of my itineraries and sleep where I already went and loved!

where to sleep Tuscany
We loved this agriturismo in Tuscany, which was a time when booking directly (in cash) was cheaper than using Booking.com or Airbnb

Step 1: Decide where you’re going and how many nights to spend there

Okay, of course first you need to know your exact itinerary. I know many people prefer to be flexible, and I get often asked how much planning I do beforehand. It depends on how spontaneous a person you are, your willingness to deal with difficult or expensive sleeping conditions, and your desire to spend time on your vacation planning your vacation.

For me, I like organization. I don’t like changing my plans at the last minute. I really don’t like feeling like I’m sleeping in a mediocre place for a lot of money because I didn’t plan ahead. I also don’t bring any technology with me except a phone (and my husband brings a proper camera), and I really don’t want to spend my vacation staring at my phone doing research and making decisions I could have made back at home on a full screen computer when I wasn’t wasting precious time in whatever exciting new place I’m in now.

So yes, you can find somewhere to sleep at the last minute anywhere in the world. There will almost always be a dorm room in a hostel or an airbnb somewhere. If you’re a good sleeper, don’t mind less sanitary conditions, or are willing to pay whatever it takes, it can be fine to book last minute, and if you value flexibility, that’s the way to go.

On the other hand, I do book everything fully refundable whenever possible, and there are filters for that as well. When there were huge rainstorms on our first week in New Zealand, and we were supposed to go snorkeling, I was able to cancel our plans and change our itinerary completely- no point going to a place famous for snorkeling when we couldn’t snorkel. If you really don’t like a place or you love it, or the weather is going to make it too hard to enjoy what you’re there for, it’s good to be able to change your itinerary to suit what you realize is best last minute.

But for me, I do the planning at home before I leave on my trip. Planning your trip is actually a major source of happiness– so the act of planning ahead of time will actually boost the joy you get from your vacation. Whereas booking it the day of during your vacation I find very stressful. The more in advance you plan, the cheaper and better your options are, so you’ll be able to stay in nicer places while staying within a teacher’s budget.

Bali
In Bali, Booking.com had incredibly affordable hotels with dozens of fantastic reviews

Step 2: Getting familiar with Booking.com and Airbnb

Okay, you’re convinced to plan ahead of time, ready to enjoy the anticipation of your trip. You’ve looked at the guidebooks, decided on which sites you must see, and how long you want to spend at each destination. Or, you’re using my website 😉, which should help you figure that out.

Now, you’re ready to book. You’ll need to make an account with Booking.com and Airbnb. Later, you might end up booking directly with hotels- I’ll explain when that might make sense later- but you’ll definitely want to make accounts with both of these search engines if you don’t have them already. You’ll want to download both to your phone to have them ready for your adventure.

Note: The link I’ve put for Booking.com is an affiliate link. That means that if you book using that link, I’ll get a commission, but you’ll pay the same amount. It’s a way for me to make a bit of money for my time writing these articles. I’m comfortable doing this only for websites I really have used myself because they’re the best option.

If you’ve never used either Booking.com or Airbnb before, first I’d look at your hometown to figure out how the app works. Notice how you can also look at the map, change filters, and see reviews.

Step 3: Deciding on which neighborhood to sleep in

Before booking, you’ll want to figure out exactly where to sleep. If you’re traveling by car, like I’d recommend to do in New Zealand, you need a place with an easy parking spot and not too stressful driving conditions- so ideally not downtown. But if you’re getting around by public transit, as I’d definitely recommend for Amsterdam, then you’ll want to be right in the middle of everything where parking is very hard and public transportation is excellent. San Francisco is in between those two extremes.

If it’s a tiny town, like most of Bali, it won’t matter too much where you’re sleeping as everything will be walkable or a short cheap ride away. In a much bigger city but with affordable taxis and/or good public transit, first look at the sights you want to see on Google Maps, and then decide what neighborhoods are nearby, like in Jakarta or Yogyakarta.

Step 4: Using Booking.com and Airbnb

I would always recommend checking both Booking.com and Airbnb. If you’re booking just 1-2 vacations a year, and your trip is two weeks or less, then it’s worth going to their website and seeing if you can get the same price or better directly through the hotel. It could be cheaper, they might have package deals that are appealing to you, and you might learn more about the rooms and different options on their website.

For example, the place we stayed at in Raja Ampat, Indonesia, with the best snorkeling I’ve ever experienced: that place I booked directly through the hotel. It was more affordable and they had a package that made sense with the activities we were going to do anyway. If you’re going to spend 5 or more nights in one location, then I’d definitely book directly with the hotel, and you could try asking for a discount for a longer stay- many will do that.

Beautiful hotel Raja Ampat book direct
We booked directly with this wonderful hotel in Raja Ampat for the best snorkeling experience of our lives…and we got to stay in this beautiful room! We wouldn’t have gotten this deal if we hadn’t booked directly with the hotel.

But if you’re mostly staying 1-3 nights, and you have a lot of different places, that will take too much time and rarely lead to any savings. Hotels often have stricter cancellation policies than Booking.com, which could leave you trapped if your plans change.

You’ll want to check both Booking.com and Airbnb to figure out which place will have the best option for you in the location you’re going to. In general, Airbnb is better if you’re traveling in a group of 3 or more (friends or family), and in more expensive locations (Europe, North America, New Zealand/Australia, Japan, South Korea, Costa Rica, etc.). But it’s not always, and sometimes you’ll be able to find an incredible place on the site you weren’t expecting. So check both!

Booking.com

Okay, you’re ready to book. You have your dates and number of guests. Now…there are 1000 options- how to choose?

  • First, set your filters. I have high standards: my husband is a light sleeper, and we both care about quiet, clean, safe, and a good location. Of course, we’re also on a teacher’s budget.
    • Rating: 9.0 or better. I almost never stay anywhere that has less than 9.0/10.0 on Booking.com. Yes, some people are crazy and write bad reviews for no legitimate reason. But that’s why I also choose places that have ideally at least 50 reviews or more. Occasionally, I have to stay at places with only 20 or 30 reviews, and very rarely, there are simply no options above 9.0, but that almost never happens if you plan ahead of time. To be honest, I would also look for reviews from people from your own country (so if you’re American, look for other American reviews). Those reviews are likelier to have similar expectations to you- and if almost all reviews are from a country very different from your own, you might not get what you expect.
    • Free cancellation: Again, sometimes you’ll want to stay longer, or leave sooner, or the weather or some other unforeseen event will ruin your plans, and you’ll want to be able to change things without a penalty. 48 hours’ is normally plenty, and even a week’s warning is generally sufficient.
    • Budget: Obviously this will depend on what you find reasonable and where you’re going. In Southeast Asia and Latin America, I set it to $20, sometimes $30. In New Zealand and Costa Rica, I set it to $50.
    • Location: You can decide on a distance from the city center, and filter for that depending on whether you’re renting a car. If you have a car, then filter for parking. If you don’t, keep yourself within a kilometer or two of where you want to be so you can walk.
    • If you still have more than 50 options: Free breakfast! I only book places that have either free breakfast or a kitchenette. You can’t travel on a teacher’s budget and go out to eat for breakfast, lunch, and dinner. Eating breakfast out will take up a lot of precious sightseeing time and energy as well as eating up your budget. Whether breakfast included is standard varies greatly by location- easy in Indonesia, for example, but almost impossible in New Zealand. If you’re in a spot with many 9.0s with free cancellation, then go for the free breakfast!
  • Okay, you’ve used your filters, and you still have 20 options. Now, press the “sort” button and sort by “best reviewed first” to have the best reviewed one at the top. Does it have more than 50 reviews? If it has less than 20, skip it. If it has 20 or more, press the “heart” to save it to a new list. Title it the name of your trip (like Jordan 2024). Go down your list and add all the ones that meet that critirion.
  • Next, where it says, for example, 9.2, click “Show summary,” and read summary of reviews there. Under “Location,” make sure it’s at least 9.0, ideally higher, like 9.5. In cities you don’t know well, especially if you won’t have a car, this is really important. Other guests will tell you whether it’s a place that is convenient for what you want to see and feels safe.
  • Lastly, if there’s something that’s really matters to you, go to “See detailed reviews,” and “Filter.” There, you can sort by key word, either words that already come up often like “clean,” “quiet,” etc. or your own by clicking “search.” Since my husband is a light sleeper, I always search “quiet” and “loud” and “noisy.” This last check helps me avoid anything that is likely to ruin our night.

Now that you’ve narrowed it down just to places that should all be good to stay in, with excellent reviews with ideally at least 50 reviews, free cancellation, maybe free breakfast, and great locations, it’s time to decide.

How to book: Press the “Sort” button at the top, and decide whether to sort by “Best reviewed first,” if you’ve made your budget filters truly comfortable with you, and decide between the top 3 options based on photos and reviews. Or, sort by price, lowest first, and decide which of those top 3 options are the best fit for you. They should all be good with your filters, so there won’t be a wrong choice!

Airbnb

In some locations, Airbnb will be far cheaper, more plentiful, and better than traditional hotels. Iceland, Norway, and New Zealand, for example, had much nicer options at Airbnb than Booking.com. If you’re traveling in a party of more than 2, whether you’re with a group of friends or family, it’s often cheaper (and more fun) to rent out an apartment or house together than all rent separate hotel rooms.

First, put in the location you want and number of adults.

Next, zoom in on the map to where you actually want to sleep- so if you’re looking for an Airbnb in Oslo, Norway, make sure it’s zoomed in so that only the city is in the map area (otherwise it’ll show you places nearby but in other towns- not acceptable if you won’t have a car).

Now it’s time to filter:

  • Price Range: This will of course vary depending on how many people you’re booking for and the location. For Norway, I was looking for 4 people, so my budget had to be much higher, at least $200, or even $350 for nicer places…but that was still cheaper than hotels.
  • Type of Place: If you’re flexible, do any type to get the most affordable options other people love. But if you’re traveling with a bigger group and/or want privacy, select “Entire home.” Otherwise, you will have shared spaces, like a shared bathroom, kitchen, entrance, etc. Your price range will make this clear, and it also depends on how much you want to interact with strangers. I’ve almost always had very positive experiences with hosts, and it’s much more affordable.
  • Rooms and beds: Think about what you’re comfortable with, and make sure you have enough bedrooms, beds, and bathrooms to feel at home!
  • I skip “Top-tier stays” and “Property types” to keep my options open.
  • Amenities: For me, since almost no Airbnb have free breakfasts, kitchens are a must. A fridge, an electric kettle, and some basic cutlery and dishes means we can make our breakfasts and start our days affordably and quickly. Just buy some basic oatmeal or yogurt, tea/coffee/milk, bread jam/peanut butter, and you have really quick breakfasts and lunches for a week or two. Long lasting milk can be really helpful. Enjoy some dinners out, but use your daylight hours to explore your new location instead of sitting inside a cafe.
  • If you have a car, filter for free parking.
  • Unless this rules out most places, click on free cancellation: You’ll still need to give some notice, like 48 hours, but free cancellation gives you the ability to change plans if you need to.

Okay, now I really don’t like that Airbnb doesn’t let you organize their search results or filter by number of reviews or even by review score, so once you have your filters set, it’s a mess of Airbnbs that meet those requirements but might have terrible reviews or very few reviewers.

Make a wishlist by clicking the heart next to all the places that:

  • Have at least 20 reviews. Ideally more than 50, but that might be hard in some areas.
  • Have at least 4.8. You definitely don’t want to stay someplace less than 4.5. In fact, if there’s more than 2 reviews that are 3.0 or lower, eliminate it. Airbnb is less regulated than proper hotels, and you want to feel safe and comfortable. Especially if you’re traveling alone, you want to feel safe. If other people, even just 3 people, have had bad experiences, don’t go there.

Once you have your wishlist, then you can be more picky. Go back through, and if you have enough to eliminate ones with less than 30 or 50 reviews, do that. Go back through, and eliminate the ones with less than 4.9. By now, you should have places that are all great options. Double check the map and make sure they all make sense for where you want to be. Then, let the price, photos, and reviews make your final choice- but know that all of them at this stage should be good places to sleep!

Final Thoughts

You’ll definitely want to have your cell phone working when you’re traveling- at least one person in your traveling party, and that person should have Airbnb and Booking.com on their phone with all of the confirmations. You can check your itinerary, double check how you’re paying/what you’ve already paid, and make sure you get what you’ve requested. I always buy a local SIM card, and that’s normally very easy at the airport when you arrive (and some places, like the E.U., will have 1 plan for the whole region). I don’t print out confirmations because I always have my phone and a portable charger, but if that makes you nervous, print away.

Booking ahead by at least a month or two will get you fantastic options. If things change last minute, then you’ll probably need to lower your standards, so just check the reviews very carefully if you need to book something with lower reviews- make sure it’s not for anything that will make you uncomfortable.

I’ve had wonderful experiences traveling alone as a single woman and as a couple with Airbnb and Booking.com, and I hope these tips help you feel confident booking your vacations too! If you don’t have too many places to book, and you’re spending more than a couple nights at a place, remember to check their website and see if you can get a better deal directly. Have a wonderful trip!

Related Post