Because of high demand, looking for a rental for the next summer in the Hamptons begins in October or November the year before, when prospecting renters drive out from the city or fly in to enjoy leaf peeping and pumpkin picking interspersed with viewing houses. It can even begin at the end of a summer rental, during the last few whimsical days of summer when everyone is dreaming of the next one. Either way is preferable while pools are uncovered and grass is still green, to experience a true feel of the environment around the home.
For those who work in New York, a quick drive to the Hamptons for a monthly rental or all-summer rental is increasingly attractive compared to a traveling vacation during the summer with the family. Reasons include long lines at airports to even board a plane, expectations of lost luggage and stress, increasingly unsafe and unpredictable conditions in Europe— and the prospect of being able to take along the family dog and/or nanny. A home-away-from-home rental often becomes a serious search for buying a home here once renters fall in love with the lifestyle and realize the many benefits of buying and renting out their home the months they are not there. It’s a good “try-on-and-see-if-it-fits” strategy.