Home Away from Home


My favorite trip as a child was less than an hour away from Chicago—my family used to rent a small cabin on a small lake in the middle of absolutely nowhere on the Michigan/Indiana border for a week in late summer. My sister and I spent morning, noon, and night swimming in the lake. The community was all of a square mile. The nearest paved road was several miles away. There was no trouble for us to find and no trouble for us to make (and believe me, we tried). We were allowed to generally run wild for a solid week.

No surprise, then, that my favorite trips as an adult are still of the rented cabin variety. The very short-term rental has all the same complexities as camping—tiny, primitive kitchen, a solid week of meal planning, opportunity to explore a new area of the country, an opportunity to commune with nature, no TV, no internet—without all the hassle of things like “equipment” and “spiders.” The hubs and I short-term rent at least once a summer.

As in any vacation, your first step is to decide where it is you want to go and how much you want to spend. Short term rentals vary in quality from a trailer to a penthouse, depending on how much you’re willing to spend. I have rented homes from as little as $50/night but seen them available for rent all the way up to $1000/night. The differences generally amount to location, size, and amenities. Your second step is to start to scour reputable websites like VRBO.com (my personal favorite) or HomeAway.com. There is a fee to list a property on these sites, which means that if a psychopath is going to list his home, he has to pay for the opportunity. Most psychos prefer to lurk on free sites like Craigslist.

Third, search until you find a property you like and wish to rent and then act quickly—these properties go fast. If you think you want a cabin on a lake, rent it a year in advance. No joke. The owner of the condo should send you a contract right away and will usually ask for 50 percent of the payment up front and the remainder about a week before your stay. This is pretty normal, but don’t be stupid. Ask if you can use a service like PayPal. Don’t send a check without a contract. Trust your gut here—if it feels too good to be true, it probably is. Except for this one time when the owner of the rental property is was a Nigerian prince who promised me 10 percent of his fortune for cashing a check for him. I mean, but what are the odds of THAT happening again?

Don't leave these sitting around. Clean up after yourself!

Don’t leave these sitting around. Clean up after yourself!

Finally, once you get to your new, temporary home, don’t be a jerk: clean up after yourself, take out the garbage, strip the bed, and do some laundry (if you can). Leave the home you rent in better condition than you found it. There is an underground rental mafia and you will get blackballed if you’re a shitty renter. In most cases, you’re renting from someone who occasionally rents their beloved family property to make ends meet. They have literally opened their home to you. Come on. Don’t be that guy.

A couple other things to note about short term rentals:

  • Short term rentals are fantastic for group trips. They generally have more sleeping areas than just bedrooms and accommodate lots of people very well.
  • Check the rental price against that of the local hotels. You can generally find a short term rental—complete with kitchen and separate bedroom—for at least a comparable price to a hotel.
  • If you are planning on renting more than one hotel room, you will generally come out ahead with a short term rental (vs. a hotel).
  • Short term rentals are available all over the world. Really.
  • The owner will likely provide you with a list of Dos and Don’ts and a list of check in/check out procedures. Mind this list.
  • Develop a relationship with the owner. Repeat business will get priority, which means better weekends during the summer and no cleaning deposits.
  • On negotiating the price: you can attempt to open negotiations on the nightly or weekly price of your short term rental. How far you get will depend heavily on the person you’re renting from and their tolerance for negotiation (which is not high for a lot of people). Remember that you’re renting someone’s house and that you’re not purchasing a used car. That is, be reasonable and polite. If you ask someone if the quoted price is the best they can do and they say yes, don’t push. Just walk away if it’s out of your price range.