Booking Accommodation as a Solo Traveller

So, you know here you’re going and you’ve booked your transport. Now for somewhere to stay.

It’s a truism to say that where you stay can make or break a trip. I have learnt this partly by reading the small print and partly by making the usual traveller’s mistakes: assuming a 'good deal' really is good, trusting a platform to sort things out, underestimating how far somewhere is from the station, or discovering too late that a single room can mean 'tiny room with a view of the bins'.

So this is not just a list of booking tips, it’s a practical routine I now try to follow before I commit money, time and holiday expectations to yet another bed in yet another place.

Choose the Stay That Suits the Trip

First, decide your style of accommodation. More pampering in a hotel: a hotel usually means more service, more predictability and, if you are lucky, breakfast, reception staff and someone to sort out problems. Travelling solo, I usually plump for a hotel - more chance of someone (other guests) to talk to and nearly always, a person at the desk, to advise on exploration. Or there are hostels in many large cities - less expensive, less comfort, more company.

I'm also very happy with a good Airbnb room. Again, it may offer more opportunities to be sociable and a host who can help orientate me. Airbnb hosts generally like meeting people, have good knowledge and a vested interest in making you happy. First of all, I'm interacting them them daily and secondly, good Airbnb reviews are essential to the business. Airbnb aren't really happy with anything under five stars - which they view as normal. Collecting good reviews turns you into a Superhost.

Another option is a whole place to myself. An apartment offers more freedom, more space and the possibility of cooking (if that is a good thing?)). But, no daily maid service here, no front desk (usually) and a host who may be hard to contact. This means relying heavily on reviews, photographs and house rules being accurate.

My list of points to look for includes secure entry, well-lit surroundings and repeated comments about safety and cleanliness in reviews. Also, depending on where this is advertised, to allow for cultural differences: 'standard' and indeed 'Five Star' can mean very different things in different countries.

Location and Transport

Location matters as much as the bed, and this is where I have learned to be much more cautious. To check how close the accommodation is to public transport, the places I actually want to visit, shops, restaurants and safe routes back after dark. A bargain hotel is not a bargain if it requires an expensive taxi every night, or a stressful transfer after a late flight. I can tell you it's no fun wheeling a suitcase a mile up a cobbled hill, or trying to direct a grumpy taxi driver in a labyrinth of city streets. Before booking, check the route from the airport, station or ferry port, the cost of local transport, the time of the last train or bus, and whether the neighbourhood is practical for the way you travel.

Late arrivals mean making sure check-in is possible and that there is a staffed desk, a key safe, a code or a host who expects a phone call.

If I'm relying on public transport, I have to remember to look carefully at the map, rather than just the distance. A hotel two miles away with a direct tram may be easier than one half a mile away, up a hill, with no pavement. If I'm moving on every day, being close to a station matters more than charm. If I'm staying put for a week, a slightly quieter area with good buses might be ideal. if I've got a big suitcase or an early departure, 'near' may not be near enough.

If I'm renting a car, parking is crucial. Is it guaranteed, paid, secure or simply 'nearby'? I've known 'parking available' to mean tiny car park, six spaces, first come first served. Or even worse - 'You should have called to reserve it'.

AI - A Planning Assistant, Not a Final Authority

I’m finding AI to be increasingly useful at the messy beginning of travel planning. Used carefully (and cautiously) it has a whole host of skills: recommending destinations, comparing neighbourhoods, suggesting itineraries, grouping activities by location, (with planned routes) producing packing lists, drafting messages to hotels, translating questions and arranging all kinds of transport.

But it only works well if I give it detailed context: goals, destination(s) dates, budget, reasons for travel, preferred pace, interests, dislikes, accommodation style and preferred modes of travel.

Prompts That Make AI Useful

Recently, for example, I used this prompt: 'I am travelling to Lisbon for five nights in June, solo, mid-range, and I prefer safe neighbourhoods near the Praça Marquês de Pombal. Find me a hotel.' I knew the Praça was a central transport hub, but you could instead replace it 'with easy public transport and local restaurants rather than nightlife'. Or: 'Compare three areas to stay, including pros, cons and transport links.' Or: 'Here are three accommodation options. Compare them for location, cancellation terms, hidden costs, check-in arrangements and likely convenience.' You could also paste in a list of possible hotels or apartments and ask AI to produce a comparison table, a list of questions to ask the property, or a warning list of anything that looks unclear.

Moreover AI never gets upset if I ask it to change something or add in extras. The only limitation is the credit on the plan you have. ChatGPT has strict limits on what you can do each day, unless you pay. Google is unlimited, but less reliable. Under my questioning, Google happily admitted that it is programmed to sound confident, even if it is unsure about an answer!

My German Test Run

The first time I got to grips with AI, it planned me a trip to Hamburg. It gave me some really useful tips on places to visit and told me about the cheap German train pass and how to buy one. Brilliant. It also planned my day trips for me. Not so great, as it turned out the main train line to Berlin, which I needed to use, was closed for repairs all summer.

So, never let AI be the final authority. AI only presents what if finds online. It doesn't know if it is correct. Prices, opening hours, routes, visa rules, cancellation terms and availability change constantly. Ask AI to help you organise the research, then verify the facts on official transport sites, hotel pages, booking confirmations and current reviews. AI is excellent for asking better questions and spotting what you may have forgotten; it is not a substitute for reading the small print or checking the actual booking page.

My Baltics Itinerary

I've just used Google to plan me a summer trip to the Baltics. It did a pretty good job of producing a detailed itinerary with buses, and trains, reasonably priced and well located accommodation and key sights to visit, with directions and distance from my lodgings. It even priced it all up for me.

I asked ChatGPT to check it. It congratulated me (patronisingly I thought) on producing 'a better than average' plan, then suggested a few minor tweaks. Nothing major. The itinerary is now parked, ready to be revived - and, of course, checked manually by me - before I go ahead next year.

When to Book

Timing can matter almost as much as the site you use. I usually book well ahead for better availability and steadier rates,- not to mention peace of mind. Google tells me the optimum time is one to three months beforehand, but don't try that, in January, in the Bahamas. Last-minute deals can pop up if hotels have empty rooms to shift, but I've been badly bitten in cities, especially on a Saturday night, when late rates can soar.

I do try to make my dates flexible, (compare weekdays with weekends), and look at off-season or shoulder-season prices. Occasionally, I set price alerts, on booking platforms, or travel search sites so I can see whether a place I like the look of is dropping or rising, rather than relying on one snapshot.

Use Reviews, But Read Them Like a Detective

TripAdvisor, booking platforms and map reviews are useful, but they are not gospel. I use them, but I try to read them forensically. I don’t just look at the numerical scores. I read the most recent reviews, check the traveller photos, as well as the official ones, and match the pictures to the written description. I particularly look for comments on room size, stairs, lifts, bathrooms, cleanliness, noise, heating or air-conditioning, and whether the promised facilities really exist. If the room type, bathroom arrangements, parking, breakfast or check-in procedure are unclear, I message the property before booking. A vague answer is information too - as is being ignored.

One angry review may tell you more about the reviewer than the room, and one glowing review may be meaningless. If several people mention the same thing - noise, weak Wi-Fi, steep stairs, poor cleaning, helpful staff, a wonderful breakfast or a misleading distance from town then it is more likely to be be a true reflection. I click on the one and two-star reviews, and avoid if there are a lot of them.

I try to be especially alert to reviews that sound excessively dramatic or suspiciously similar to each other. Many are, sadly, fake - written by the accommodation providers themselves. Or, occasionally by their enemies/competition who write ridiculous undermining comments. I have honestly seen reviews that say 'the place is alive with cockroaches' or 'I was badly bitten by bedbugs'. It's a good deterrent.

Compare Platforms

I used to think there were lots of independent booking sites, but I've discovered (my friend Google again) that many sit under a few large travel groups. Booking Holdings includes brands such as Booking.com, Kayak, Priceline and Agoda; Expedia Group includes Expedia (of course), Hotels.com, Vrbo, Orbitz, Travelocity and Trivago. Lastminute.com is another familiar name people may compare when looking for late deals or packages. It is a stand-alone company, but no longer British-owned, and another behemoth.

It is still worth comparing prices, but don't assume that every site represents a genuinely different route to the property, or that the lowest headline price will remain the lowest, once extras are added. I have also seen prices shown through comparison sites mysteriously increase when I land on the booking platform itself. That cost may still be the best option, but it should be a conscious choice.

Watch the Extras

I've found I also need to be forensic when looking at the final price. Taxes, city charges, cleaning fees, resort fees, breakfast, Wi-Fi, parking and payment charges don't always appear until late in the process. Cleaning fees can add appreciable amounts to short self-catering stays, and sites do not always display taxes in the way you expect; on some platforms (like Booking.com) you can change the settings to show them more clearly.

Sometimes breakfast is included; sometimes a 'deal' becomes less attractive once you add luggage, room safe (yes, some mean places charge extra), parking, transfers or a cleaning fee.

Airbnb Requires More Research

Airbnb reviews and house rules deserve especially careful reading, and the online details are not always as explicit as I might hope. On Airbnb I always message the host and check; it is usually very easy to do this through the Airbnb site. Sometimes it is obligatory - you may have to be vetted before you can be accepted and promise not to have any parties!

My Bequia Airbnb came with a generous supply of mosquitoes. There were plenty of anti-insect contraptions, but I had to provide the tablets and coils myself. It was also up a very steep hill. My host was in England, though I didn't find that out till I arrived. It didn't stop her sending messages every day instructing me about what I could or shouldn't do.

Then Go Direct

Once I have found somewhere I like, I search for the property’s own website. Though is is not always straightforward. Smaller places may have an old website, only provide an email address, and simply fail to reply to that. Some hotel chains do not use the big platforms at all; Premier Inn in the UK, for example, is generally booked direct. Some chains offer lower prices/member rates if you join their loyalty scheme. It does not always beat the platform price, even when a chain claims it will, but it is worth checking, before you book.

Once all the costing information is gathered it's time to to contact the property directly and negotiate. To ask whether they can offer a better rate, a discount for a longer stay, breakfast included, a quieter room or a more flexible arrangement. The worst they can do is say no, and sometimes they can offer something the platform cannot.

I've found that hotels are also increasingly using WhatsApp (so no cost international calling). In the Maldives, for example, the main contact telephone numbers given were WhatsApp numbers - with varying levels of response. Direct contact with just one responsive person is so helpful. My useful Maldives people gave me room upgrades, help with arranging transport (including flights), tours and sightseeing suggestions, ferry bookings and even other hotel recommendations.

Understand Who Will Help If Things Go Wrong

Platforms are convenient and often cheaper, especially for flexible cancellation deals, but they may be far less helpful once you arrive and the room is filthy, the property is closed, the pictures were more than flattering, or the host cannot be found. In practice, you often have to negotiate with the accommodation provider yourself. That risk is greater with self-catering accommodation and privately managed apartments than with mainstream hotels, where at least there is usually a reception desk and a chain of responsibility.

When the Platform Shrugs

I have had some very bad experiences with Booking.com. In Israel, an apartment I booked was dirty and half decorated. Booking.com told me they were just a platform and that I had to take it up with the host.

Even more worryingly, in Baku recently, the hotel I had booked turned out to be closed. The hotel then told Booking.com that I had cancelled, and this was simply accepted by them, while I was wandering the streets in search of accommodation, at ten at night. They ignored all my requests to do something about it and the hotel keeps advertising on their site.

Booking direct may give more peace of mind because you have straightforward communication with the property. But be very cautious about places with self check in, where you never get to meet the host.

Different Platforms, Different Safety Nets

Airbnb, for example, can be less easy to communicate with at first, and you usually have to pay at least part of the cost up front, but, in my experience, it has better procedures when dealing with dissatisfied customers, once you get through (and that can take time - they're USA based). It tends to support the customer rather than the host - bad news if you’re hosting, as I know to my cost.

My point is not that one route is always better than another. The point is to find out who is responsible and to be clear about how I will get help before I need it.

Cancellation, Payment and Protection

I never used to worry about cancellation charges. What's going to stop me going?' I always thought. But I've had to postpone a few trips during Covid, and lately, due to my back operation and I've become much more aware of evaluating my booking risks.

I’ve learned, to my cost, that cancellation terms are not for decoration and to read them properly, especially if my plans involve uncertain transport, visas, health issues, moving between places or other travellers. Paying more for late cancellation may be sensible if there is any doubt. Free cancellation can cost considerably more, and sometimes 'free cancellation', if you read the small print, means you pay now and have to wait for a refund (which might take some time) if you cancel. Hotels.com often wants payment up front, which may be acceptable, to secure the price on offer, but check exactly what the terms are and what happens if you need to cancel. I've discovered hotels will nearly always be amenable to change the date, however, charging any price differential.

Some small print which may be helpful:

'If you book travel services together - for example flights and accommodation as a package - you may have stronger protection than if you book each element separately. In the UK, package holidays generally require financial protection, and ABTA explains that this protection is designed to help with refunds or getting travellers home if a package organiser fails. If you book a flight-inclusive package, look for ATOL protection too. This matters because a 'flight plus hotel' deal can look like a bargain, but the important protection depends on exactly what you have bought and who has sold it to you.

For separate bookings, your protection may depend on the supplier’s terms, your travel insurance, your card provider and the evidence you kept. Paying by credit card can give an additional route to challenge certain problems, and debit-card chargeback may sometimes help too, but neither should be treated as a substitute for reading the terms before you click “book”. Travel insurance is also not magic: check whether it covers cancellation, delay, accommodation failure, medical issues and the kind of travel you are actually doing. There will be limitations and exemptions.

Keep confirmations, screenshots, messages and receipts in one folder so you can prove what was promised, what you paid and when you were allowed to cancel.'

When the Refund Goes Quiet

During Covid-related cancellations, I had particularly bad experiences trying to communicate with Expedia and Lastminute.com. Nobody seemed reachable (no phone numbers), nobody seemed interested (emails ignored), and I eventually pursued my refund through my credit card provider.

Solo Travellers and Single Rooms

Single room supplements remain one of the curses of solo travel. Some places offer genuine single rates, sometimes in rooms that are perfectly adequate and sometimes in rooms that resemble cupboards. Others simply charge the same as for two people in a double room, even when breakfast for two is included. I have learnt to compare the total cost, not just the headline nightly rate, and to ask myself whether 'single' means good value or just the worst room in the building. Single supplements, at times, can double the accommodation cost for a person sharing on a tour, or cruise. Some cruise companies now operate singles only ships, but I've read numerous complaints that the cabins are no cheaper than standard double rooms. You really have to bite the bullet here and read all the small print - or call and ask.

Many companies offer to pair a solo traveller up with another, to waive the supplement. It can be a good way to make friends. But it's not for me any longer. I've suffered too much from folk who snore, or bounce in late at night and put the light on, or get up at 5 a.m., to do their hair.

Be Cautious Booking for Other People

If you are booking rooms for others, get the money up front unless you trust them absolutely. (I've been burned here too.) Otherwise, if they change their minds, forget they agreed, find something cheaper, or fail to turn up, your card may get charged no-show fees, even if the terms were pay on arrival.

Paying Ahead to Choose Your Room Location?

This was a new one to me. I was being organised and booking ahead for a hotel, in the UK, so I could go to a friend’s birthday party this autumn. Travelodge was cheap, so I booked a standard room. I was then offered a choice of room location, complete with a map of the floor, at a cost of up to £14.99 extra. I declined, so no doubt I shall end up with Saturday-night High Street noise. I do hope this does not catch on. It's bad enough on airlines, being allocated the middle seat if you do not pay up

Loyalty Schemes and Upgrades

Hotel loyalty schemes are usually worth joining if they cost nothing, even if you do not travel constantly. The real discounts often only build if you keep using the same chain, but small benefits can still appear: free water, Wi-Fi, late checkout, points, occasional room upgrades or a surprise reduction on a future booking. I'm signed up to schemes such as IHG, Hilton, Marriott Bonvoy, World of Hyatt, Radisson Hotels and Accor; Accor gave me my last booking completely free, unexpectedly, because I had accrued points I didn't even know I had.

And when you arrive, it rarely hurts to ask politely whether an upgrade is available, especially if the hotel is not full. You can also try in advance, if you have a special reason for wanting a quieter room, a better view or extra space. It will not always work, but the answer is certainly no if you never ask.

My Booking Routine

1. Decide what kind of stay: hotel, apartment, hostel, homestay, self-catering place or package deal.
2. Use AI to compare, organise and question all of the following, then verify every important detail yourself.
3. Compare different booking dates, weekdays and off-season options, and set price alerts where useful.
4. Choose by location and total price first; then use the photos and description to check that the place matches what you need.
5. Read recent reviews carefully, looking for repeated patterns rather than isolated praise or angry complaints.
6. Check the final price, including taxes, cleaning fees, breakfast, Wi-Fi, parking, luggage, transfers and other extras.
7. Compare platforms, including familiar names such as Booking.com, Expedia, Airbnb and lastminute.com, but remember many brands sit within the same groups.
8. Check the property’s own website or chain loyalty rate before booking, and consider asking directly for a better deal.
9. Read cancellation, payment and no-show terms carefully before you commit.
10. Check what protection applies: package protection, ATOL where relevant, insurance, credit card or chargeback routes.
11. Check transport links, late arrival arrangements, parking and the route from your arrival point.
12. Keep screenshots, confirmations and messages all together.

Final Thought

The best travel booking is not necessarily the cheapest. It is the one where the location works, the terms are clear, the risks are acceptable and you know who to contact if something goes wrong. I still like a bargain, and I still compare sites, but I now try to book with a little more suspicion and a lot more preparation. Do the boring checks before you travel, and the trip itself has a much better chance of feeling like a holiday..

Happy Travels!