So the question to ask yourself is — what are you going to do while you’re there, and why are you going? Are you going for relaxation, to save money, to get away from humans, to pamper yourself?

This always leads my decision-making process when I plan a trip, because when it comes to it — I’d prefer to do a vacation rental, but sometimes, you just want somebody to make up your bed, clean your bathroom, and refresh all your dirty drinkware for you so you can bask in being a bum. You can go out and about and come to a room that’s all clean and tidy and welcoming for you to mess up and wallow in and enjoy.

So, pros and cons. Let’s dive in, shall we?

THE OBEROI UDAIVILAS, Udaipur. Source: www.oberoihotels.com

The hotel

A hotel requires minimal work to book — they’re plentiful, they’re in the business of renting out ridiculously priced little rooms and making bazillions off the people coming to and fro in a city. They’ve got fancy payment systems, and established trade skill — a way of doing something thousands of years old. Like tailors, and fishermen. Since the dawn of time, there have been hotels — taverns in Skyrim, etc. etc.

You can say you’re a hotelier and everyone understands there’s a whole world of training and business and interaction tied up in that word. A ballet of “hotel management service.” And the hotels in the world who have the science of their trade down to an art form can literally blow your mind and make you return again and again, because you feel so special when they get it right. A hotel can be a really satisfying experience. It can also be a really transactional experience, depending on the skill of the hotel you’re staying in and your budget.

I once stayed in a hotel that bent over backward to take my money and made me feel special —  I was so delighted I tipped like a generous idiot and the whole time I knew what was happening, but that was how cared for I felt.

So you can book from professionals, who, in an ideal world, take care of you. But they nickel and dime you, usually. They want to charge you $250 a night for a room and $30 for parking overnight and $10 a day for your wifi (in Singapore, it’s up to like $20+ SGD a day, it’s ridiculous) and they want to limit the number of devices you can use blah blah. And the food on their menu — hopefully it’s 24 hour room service! — is going to be mediocre and stupidly expensive, and you can hear the elevator door ping every time it opens or that drunk fool next door with his loud music or like, whatever. And you eye those drinking glasses and you wash them one more time with soap and water in the sink cuz you never know, and you kick the coverlet off the bed and those designer pillows you know don’t get washed and you roll your eyes at the 15 channels on the TV. So then you start debating — hey friend, let’s split a 2-Queen room and budget this.

And then you get the folio at the end of the stay and it’s all these little taxes and fees and you feel kind of used, and it’s like:  was it really all worth it? Really?

But sometimes, you want to be spoiled and not think and you want someone to baby you and take your car and park it for you, fetch your bags, speak to you in soothing tones, bring you extra ice, and bring you an extra robe and buckwheat pillow.

So, yeah, I’m a member of Starwood and Marriott and IHG. Ahem.

The vacation rental

But then there’s the vacation rental. If you go on sites like homeaway.com, vrbo.com, airbnb.com, the access and inventory gap is closing and more and more professional rental agents and travel agents and landlords are taking advantage of new technology to make the rental market more easily available, searchable, and bookable by people on the other side of the world. There are people proud of being professional, 5 star hosts, and they are building up a new breed of accommodator (not as sexy as “hotelier” but hopefully someone will come up with something) that’s 25% listing agent + 25% homeowner + 25% travel agent + 25% hotelier.

And when people get it right — and you walk into something like this ridiculously beautiful place a friend and I stayed at in le Marais, Paris … well. Well, damn. Or you get yourself a $150 a night 3 bedroom house literally ON the beach, like ON the beach in Maui, Hawaii, and you wake up to ocean sunrises and you can go down the street to the market and buy your groceries and putter around. And yeah you have to change out the TP and put out the garbage bins and wash your own dishes and clothes. BUT. Free wifi. Tons of channels on the TV. DVDs to watch. Games to play. Books to read. No worrying about whether housekeeping is going to bust in on you while you’re in your PJs dead to the world.

Because … in a hotel, it never really feels like YOUR space, really, does it? It feels like very borrowed space, because the building you are in is so NOT a home. It’s a business first. And you are a “guest.” But probably moreso a “customer.” If you wanna be pishposh, a “client.” But it’s all business. But in a vacation rental … it really was somebody’s home! IS somebody’s home. Yeah you’re borrowing it but, at least there’s some warmth and personality to it. Some CHARACTER.

An apartment dans le Marais, Paris. Stayed here in Spring 2014! Source: Airbnb.com

If it’s a well-managed home, everything is in working order, clean, fresh, and fun. You have so much room to play in, and you can park right outside, and not feel like you’re in a hushed box of strangers. Live like a local. Experiment with local eateries you would never have discovered and walk around the neighborhood and really get to know the place a bit. Not entirely like a local, but, hey, a little taste.

Sometimes folks aren’t the greatest hosts — and homes can be misrepresented. Also if you have particular tastes — say, you aren’t into Mountain Bear chic but you’re trying to book a rental in Montana or Wyoming (I am seriously dealing with this issue right now) — then you’re going to have really dig to find a place that suits your personality. And if you don’t book well in advance during popular seasons (like, 4-6 months in advance) — the inventory within your budget with things you need (bedrooms, bathrooms, patio, swiming pool) will shrink until you’re left with slim pickings.

But when you find a gem — it can make a huge difference in the quality of your experience wherever you visit. It can literally make you sleep better and lift your mood substantially and like, boost your vacation enjoyment by like 30%. That is a totally legit metric.

Pick one!

Here are some questions to ask yourself to decide which works for you:

• What’s the budget and how much effort am I willing to put in? How much lead time do I have?

• Do I want to feel more like a local — run errands, shop for groceries, navigate the city like a local?

• How important are luxury amenities (24-hour room service, someone cleaning up after me)?

• How much privacy do I need?

• How many people are with me, and how much space do we need for our budget?

The hotel

If you’re willing to splurge and you want minimal effort, go with the hotel. Unless you’re filthy rich and you can just call up your listing agent and say “find me a house with blah blah take care of it, whatever cost,” you’re going to need to spend time looking through vacation booking listings — at least a couple hours. Depending on how thorough a person you are. You can also try to appoint a friend who loves to do that sort of thing, and have them bring you 3 options (I am often that friend) but in the end, if you’re the planner or the booker and you are lazy and have a hotel in mind and you just think of a hotel as a place to sleep and you don’t really care to put effort into where you lay your head — a hotel is probably your best bet.

The vacation rental

So the clincher is you can often get a whole lotta room and more amenities for the same price as a hotel. Which can work really well for a group of people — rather than trying to cram all of you into impersonal rooms that are on different floors, attached to each other, etc., you can get a larger home that has a central gathering place, and cook and enjoy outdoor space and downtime at your leisure together. BBQ and stuff. Rentals give you more rooms, washer/dryer, free parking, full size kitchen, multiple bathrooms, free wifi, etc. etc.

Source: www.nytimes.com

But you have to put in the work to find a reputable place that has what you want. And then you have to see if it’s actually available when you want (good listings have an up to date calendar). You also take a  higher risk when cancelling a booking so far in advance that hotels usually don’t put you through (unless you prepay to get a discount on your hotel room; hotels will often give you a 10-20% discount for paying in full in advance but you forfeit the whole amount if you cancel).

Vacation rentals are controlled my landlords and agents who are betting on income just like hotels, but the hit to them is harder than it is on a hotel if someone is a no-show. If you no-show, they could lose out on major money and it would hurt; so, they usually have stricter rules about how much money you get back (if any) depending on when you cancel. You also have to deal with the weirdness of a landlord who may be a little too nosy and helpful, or one who may be totally unavailable when something goes wrong and unwilling to help when there are issues with the property. Which is why you should do your research and avoid listings where people will highlight when these things happen in their reviews.

And if you’ve never tried a vacation rental before — go for it at least once! Even for just a weekend, it can be pretty fun. You can luck out and stay in a work of art in the middle of nowhere just to experience the glory of the wide open sky all to yourself for a weekend. I haven’t stayed at this spot, but I’ve stayed in some truly lovely places that make for some truly beautiful pictures and memories that no hotel could ever compete with.

Further reading

10 Paris Airbnb Rentals You Must Stay In Before You Die