The Hamptons winter rental season

A winter rental in the Hamptons is not a winter-only lease. As Curbed’s Hamptons desk put it, the term covers “the entire off-season from the week after Labor Day right up until the following Memorial Day Weekend.” Labor Day is the first Monday in September and Memorial Day the last Monday in May, which makes it roughly eight and a half months. If you want a lease that outlasts that, look at year-round listings separately.

The terms you will see

Each rental on Hamptons Key shows its term as the broker prints it, so read the line rather than assuming. If a listing says “monthly,” ask which months are open.

What changes at Memorial Day weekend

A winter lease that ends at Memorial Day weekend is meant to hand the house back for the summer season. Treat that date as fixed. If you want to stay, open the conversation in March or April and ask for the next term in writing. Under New York law, a landlord who plans not to renew must give written notice of 30, 60 or 90 days depending on how long you have lived there; see the notice table. If you stay after a lease ends and the landlord keeps accepting rent, the state treats you as a month-to-month tenant, but ask for the next term rather than relying on that.

Winter rental or year-round: three practical differences

1. The calendar. A winter lease has a built-in exit. A year-round lease does not, and the renewal conversation comes at a time of your choosing rather than the owner’s.
2. Tax residency. For New York income tax, the state says you maintain a permanent place of abode for substantially all of the year if you maintain it for more than eleven months, and Tax Bulletin IT-690 gives an example of a home rented out for part of the year that did not meet that threshold. A lease of about eight and a half months and a lease of twelve months may be treated differently. Read the residency page and ask a tax professional.
3. School and services. A year-round address is easier to prove for school enrollment and town permits. The enrollment guide lists the documents to ask for.

When to look

The September almanac covers the dates around Labor Day. A one-month stay in January or February is the cheapest way to test whether you want the whole season: see try a winter first.