While many consider renting in the Hamptons a purely summer activity, many people choose to do so year-round by choice or necessity. Unfortunately, finding a suitable space to call home out here is much more difficult than doing so in a major city. There's just not much inventory in the area to begin with, and there is a growing trend for year round rentals to be converted into summer only, since they can be rented at a higher rate, and many of the reasonably priced rentals are only available during the offseason. So, in the interest of providing a little assistance to year rounders, we've compiled a guide to help out.
Friend referrals: The best way to go about finding a rear-round rental is by word of mouth. Let everyone you know—friends, family, co-workers—know you're looking. Often, landlords would rather rent to someone that comes pre-approved. In fact, many people don't even publicly announce that they've got a place available and rely on word-of-mouth to spread the news.
The local papers: Dan's Papers, The East Hampton Star, The Independent, The Press...they've all got sections in their classifieds for rentals. Best to pick these up and call potential landlords the day they're published, and/or check online every day. Since there's such a limited inventory, places listed in the papers tend to go quickly.
Bonac Year Round Rentals: This Facebook group was started by locals hoping to make finding things a little easier. Members either post what they're looking for or what they've got available. You've need to send a request (and get approved) before you can post, but you can see what everyone else is talking about.
Craigslist: Good ol' craigslist is not nearly as popular out here as it is in major cities, but every once in a while a landlord (most likely in an effort to save money) will post an available apartment/house/room in the housing section. Using different keywords to search—"hamptons", "Sag Harbor", "Montauk"—usually yields the best results.
Converting a summer rental to year round: The most expensive and most reliable option is to find a summer rental. Take the July-August rate, add 25% to that and divide by 12. Many homeowners would be happy to be have a year round tenant: an occupied house is less likely to be burglarized or suffer off-season damage. Of course, heating costs can be high, as well as landscaping, snow plowing, and so on. Try to find out rough ideas for these costs beforehand.
Good luck, and see you in the IGA in February!