I was talking earlier today with a coworker about the vacation rental he was splitting with a few friends of his. He’s renting a ski house with a few buddies of his for the winter. Anyone who has rented a ski house knows that not all the rooms are the same, and we were discussing how they were splitting the rooms. There’s usually a nice comfy master bedroom often with a private bathroom. Then there are the smaller rooms, often containing tiny bunk beds. Given the disparity in accommodations, the master bedroom is usually highly sought after especially amongst vacationing sets of couples.

The question is then how do you decide who gets which room? For a shorter term rental I think it’s best try to be accommodating. For example if there’s one couple and three people who are are “alone”, the couple probably should get the nice room with the private bath. I think most people would agree on that. The problem is that more often than not, different individuals or couples have similar claims to the nicer room. Personally I’m ok with luck deciding the matter, but I generally don’t care that much about where I’m sleeping. I used to take a trip with a few buddies of mine to Whistler, and what we used to do was play cards each night for choice of sleeping locations. We played Asshole, and the rank at the end of night determined which bed or share of a bed each person got. The Asshole slept on the couch. We felt that was fair if not equitable.

I know others who think that the person who has done more work to book the house should get preference. On the surface this seems only fair. If you’ve done more work, you should reap the rewards of that work. However that begs the question of who gets the privilege of booking the house? Often times who does the booking is an arbitrary decision, other times its a perk more than a responsibility. Many people want to be the one booking because it allows for more control.

Like any matter concerning money and people, the clearest way to avoid problems is to spell things out in as much detail as possible beforehand. Don’t all show up and drop off your stuff in the master bedroom. I say if you think the choice of rooms is going to be an issue, set the terms of choice before arriving and make it financial. For example when a friend of mine and her roommate had to decide who got which room in their 1500 apartment they put out silent bids for the bigger room. The person who bid higher paid the average of the two bids. So my friend put in a bid of 800 and her roommate bid 900. Her friend got the bigger room and paid 850 while she paid 750 for her smaller room. This method gives the person who values the better room the better room at price that is fair to all involved. You can extend this method across multiple people and rooms by requiring a bid for each room.