Short-Term Rentals: Your Alternative to Hotels

When I was looking for a place to stay in Chicago for ABA TECHSHOW, most of the hotels in the area were either unavailable or cost more than what I cared to pay. A friend suggested that I check out Airbnb and rent someone’s bedroom during my stay.

Companies like Airbnb, VRBO, and Couchsurfing connect travelers with residents who are willing to rent or sublet their homes (otherwise known as the sharing economy). Most rent on a short-term basis (between one day to a few weeks) but longer arrangements are also possible.

There are some benefits to using a short-term rental. You can get a well-furnished room for a fraction of the cost of a traditional hotel room. Also, if you are new in town, your host can serve as a guide to help you get around. If your host is in the same line of work as you, he might also be a potential networking contact.

On the other hand, some hosts may not provide you with the traditional amenities that hotels offer, such as toiletries, towels, room service, and in my case, a functional bed. Also, there are isolated incidents of hosts assaulting or robbing renters.

The Airbnb Experience

I checked out the listings in downtown Chicago on Airbnb, and I was impressed with the variety of places available. There were several condos near the Hilton Chicago where ABA TECHSHOW was being held. But there were also rooms available in smaller homes just outside the city. Each room was unique. Some were well decorated while others were as bland as white rice.

I ended up choosing two places to stay. The first place was $90 per night and located near the top of a high-rise condo about three blocks from the Hilton. A picture of the bedroom displayed a spectacular view of the city and Monroe Harbor. There was free wifi. The images in the listing did not show the bed I would be sleeping in, but at the time, I didn’t think much of it. The owner is a financial planner but considers himself a hipster

The second place was $85 per night, and the apartment was located in Chinatown. I chose the place because the apartment looked spotless, had free wifi, and a small dog to keep me company. It was also located close to some restaurants my friends recommended. Finally, the place was only a block to the subway where I can take the Blue Line back to O’Hare Airport.

I landed in Chicago Thursday night. During the long ride on the subway, I received a text message from the owner of the condo:

“Steven, I rented the master bedroom to someone else for the night. Hope you don’t mind. :)”

While I didn’t mind sharing the condo with someone else, it was disappointing to get this literally at the last minute. Fortunately, my roommate for the night was a woman who was in town to attend a political science conference. After some small talk, she showed me to my room:


Thankfully, the bed was more comfortable than it looked. But I did wonder whether the sheets were clean.

Should Lawyers Use Airbnb?

If you are on a business trip, using short-term rentals as lodging requires discretion, particularly when it comes to safeguarding sensitive information. Here are a few things to keep in mind before using a short-term rental arrangement.

Security is Questionable At Best

If you plan to work in your room, it may be better to stay at a hotel — especially if you are bringing sensitive documents like financial statements, proprietary information, or customer lists. While the chances of the host stealing them are small, there is a better chance that you may forget them when you check out. Similarly, if you plan to have lengthy, sensitive conversations with clients or opposing counsel, your conversations are more likely to be overheard than they would be at a hotel.

Also, do not assume the wireless connection your host provides is secure. If you are using your host’s wifi, be careful accessing bank or credit card accounts, or your firm email. Use a VPN or your smartphone’s data connection, instead.

Check to See if Short-Term Rentals are Legal

Airbnb and VRBO have a strong presence in most major cities. Some cities are turning a blind eye while others are regulating and taxing short-term rental transactions. But it is illegal in a few cities, including Los Angeles. And since short-term rentals are a relatively new phenomenon, it is unclear whether owners would have to follow state innkeeper laws or landlord-tenant laws.

Violations will likely result in penalties to the host only. But you do not want to place yourself in an awkward situation where a city inspector makes a surprise visit and tells you to leave. Also, short-term rentals have become illegal mostly due to residents complaining about unruly tourists congesting the neighborhood. So if you are staying in an area where the legality of short-term rentals is in question, it’s possible that neighbors would spy on you or even harass you.

Trust Your Gut

So you found what looks like the perfect place to stay. The location is excellent. The rate is reasonable. The room looks clean. But something does not feel right. Perhaps everything seems too good to be true, and you get the impression that the host is not disclosing something important. Or the political posters in the living room make you wonder if the host is on any medications.

Whatever the reasons are, if you do not feel comfortable do not book the room. If you think something is going to go wrong, then it probably will.

Using a short-term rental was an interesting experience. I liked the traditional feel of staying as someone’s guest. But at the same time, I began to appreciate the many little things that hotels offer. If I am traveling for fun or to attend a conference, then I may use Airbnb again. But if I plan to work in my room and speak with my client over the phone until 1am. discussing the specifics of tax returns and bank statements, then I will choose to stay somewhere confidential and secure.

Featured image: “ Low section of young businessman sleeping beside suitcase in hotel room” from Shutterstock.


  1. Avatar legalofficeguru says:

    Another option (one I employed frequently in my days of doing business travel): If your stay will be a week or more, or you’re traveling with others, contact nearby apartment complexes and ask whether they’re partnering with any local corporate housing vendors, then contact the vendors for openings. Large apartment complexes often have furnished apartments in less-marketable parts of the site available for short-term rental for business travelers.

    (This Airbnb thing sounds seriously sketchy.)

    • Avatar Holden Page says:

      I’ve stayed in an Airbnb a couple of times. I’ve enjoyed my experiences, but it is certainly not for everyone. My suggestion is you pick a place with a lot of reviews with actual comments for feedback. Also look up the neighborhood. This has served me well.

      Also, if it seems like it will be sketchy, then don’t do it. But in general, I think Airbnb is pretty safe.

  2. Avatar Lisa Solomon says:

    I stayed in an Airbnb for the first time for 3 nights when I attended my 25th college reunion. The host lives at the property and rents out a few rooms (3 or 4) through Airbnb. She provides breakfast and free wifi (I did not use the wifi, opting to use my cell phone data plan when working on my ipad). The place was spotless and quiet, the bed was comfortable. The neighborhood was safe and quiet. The host has a lot of five-star reviews. The cost was much less than the local hotels were charging for that weekend.

    It sounds like one red flag for an Airbnb listing is the absence of a picture of the bed (which, after all, is more important than the view).

    If you’re concerned about security, take your laptop (or ipad) and any documents with you any time you are away from the property.

  3. Avatar Alex says:

    I’ve had good luck with airbnb in a couple different places. In really competitive tourist markets it ends up being comparable to a hotel. I’ve also had good luck with priceline. Turns out Shatner is a good negotiator. Priceline, where you pick an area and set a lowball price to see if an anonymous hotel will take you, actually ended up being much cheaper in Miami Beach. Airbnb was $140+cleaning fee for a room in a house and Priceline ended up being $125 for a pretty nice suite. Who knew I’d shill for priceline?

    At higher pricepoints both Airbnb and Priceline get you a lot of bang for the buck.

Leave a Reply