Fenster writes:

The internet has made short term home rental a snap for both renters and hosts.   We live near Boston but have a second home in upstate NY.  And I recently took a job that requires me to be in New York City for several days a week, and I have a tiny place there.  So our housing costs are stretching us and we have started to rent out.

We thought about the relative advantages and disadvantages of VRBO, the leader in such rentals, and the newer, hipper alternative, AirBnB.  We opted to rent the upstate house on the staid and family oriented VRBO, and have not been disappointed.

Hello, We’re traveling to NY to visit family and are considering spending a few days near Fair Haven. Possibly heading to the Sterling Renaissance Festival and doing some fishing with the kids. According to VRBO, your home is available on the dates we are considering, but I was wondering… how is the water near your dock? I know there’s been a drought so I’m concerned that the water may be too low to actually fish from the dock. Also, how far is the dock from the house?

By contrast I use the ultra-trendy AirBnB to rent my micro-apartment in Brooklyn Heights, in an old mansion right on the Promendade overlooking Manhattan.  I list it as “weekends only” and even as “multiple weekends only” since NYC is cracking down on short term rentals when the host is not present, as is typically the case with AirBnB. 

I have been somewhat successful getting the pied-a-terre crowd to use it for longer periods over multiple weekends.  Still, the pictures of the Manhattan skyline on my listing have great appeal, and AirBnB’s reach is broad, so I am forever getting emails from the international set–Maria from Caracas, Bella from Prague, Simone from Provence–looking to rent for a few days or during the week when I am present.  A lot from single women, too, as it turns out.  But not all: