A cluster of exclusive seaside communities stretched along Long Island’s South Fork, The Hamptons has long since served as a summer escape. New York’s eastern enclave counts long stretches of beach, dramatic dunes, and pounding surf among its natural highlights, though its restaurants, bars, and boutiques certainly play a role in attracting visitors to the Hamptons. Rentals are the preferred choice of digs for most visitors, so why not check out this guide and join in the fun? Coming up, you’ll find tips about when to start looking for Hamptons house rentals, the best time to visit, where to stay, and more.

Planning your Hamptons vacation

A little planning goes a long way when you’re trying to score your dream vacation home, so let’s look over the basics of renting in the Hamptons.

Best time to visit the Hamptons

From Memorial Day to Labor Day, the summer season in the Hamptons sees a steady flow of well-heeled visitors. It’s the de facto time to visit and a time that will rarely disappoint. In contrast, Long Island’s South Fork empties out between September and May, bringing with it a chance for off-season visitors to enjoy, not only a respite from the crowds, but also near-deserted beaches, easy-to-make dinner reservations, and wine tasting in Sagaponack.

When to book Hamptons rentals

Hamptons rentals often stand empty until the last week of May, but the East Coast’s rental season kicks off a whole lot earlier than that. Most renters will start looking for their ideal summer vacation home in the Hamptons after Presidents Day celebrations are done and dusted – though the early birds often start checking out rentals just as soon as they’ve welcomed in the New Year. The earlier you start, the more choice you’ll enjoy, especially if you’re after something specific like pet-friendly Hamptons rentals.

How to get to the Hamptons

While it’s not unusual for A-listers heading to the Hamptons to arrive in a helicopter or onboard a yacht, most Hamptons-bound visitors drive in on the Montauk Highway – either in their own wheels or on the Hampton Jitney bus. There’s also a seaplane service between Manhattan’s 23rd Street and East Hampton. For those heading to Hamptons vacation rentals from further afield, flight options into New York include those services touching down at JFK and La Guardia.

Hamptons vacation homes styles and more

Now you’ve checked out the basics, you can start deciding what type of Hamptons vacation home will suit you best. You’ll also learn a little about the cost of renting in the Hamptons.

Choosing your Hamptons rental

There’s a huge amount of choice on the menu when it comes to renting in the Hamptons, so you can be sure of finding a dreamy home to suit – whether you’re making memories with family, friends, or both. For romantic breaks, a Hamptons cottage rental is a popular choice, while sharing friends can sit pretty in beachfront rentals with pools. Sprawling villas and look-at-me mansions with all the trimmings tick the box for travelers looking for luxury Hamptons vacation rentals.

How long to stay in the Hamptons

Settling into an oceanfront rental for an entire blissful summer is no doubt on the wish list of many travelers, but there are plenty of other options available if long-term Hamptons summer rentals are off the agenda. If time is short or you’re keeping an eye on your budget, weekly and weekend rentals in the Hamptons are a great alternative. Short-term Hamptons house rentals can be snapped up quickly, though – so the early booking mentioned earlier becomes something of a necessity.

Cost of renting vacation homes in the Hamptons

Let’s not mince words, the cost of renting a vacation home here can be high – as in six, seven, or eight figures kind of high, especially if you’re going for a long-term stay in a luxury Hamptons rental. Off-season rates will always be the lowest, though both June and early fall can be sweet spots for those looking for cheap Hamptons rentals. You can also cut costs by splitting the rental rate with friends or opting for a shorter stay. Some rentals include a beach permit, but these should be viewed as a potential extra cost – along with any security and utility deposits.

Hamptons vacation home destinations

The small print is over and done with, but you still need to choose where to stay. Here are three awesome spots to score rentals in the Hamptons.

History meets happening in East Hampton

With almost four centuries of history, there are few places in the nation that were settled earlier than East Hampton. Even today, this popular Hamptons destination counts historic windmills and gray-shingled homes among its must-sees. Elsewhere, you’ll find boutique shopping, top-notch restaurants, and a serious party scene all add to the reasons to nab a vacation rental in East Hampton. It’s the beaches that are the biggest draw here, though – the family-friendly Main Beach and the quieter, gay-friendly Two Mile Hollow Beach just two of the places to find your perfect spot on the sand.

Shopping and celebrities in Southampton

The multi-million-dollar mansions peppered around Southampton give this long-time Hamptons summer destination an air of old money, though it’s the celebrities and designer shopping that give it a modern flavor. Southampton rentals put you close to sandy Cooper’s Beach and the Southampton Hunt and Polo Club, while yoga and wine can be enjoyed in the grounds of the Wölffer Estate Vineyard in nearby Sagaponack. Bridgehampton vacation rentals are also just a quick jaunt down the highway – and on the doorstep of a lovely Main Street filled with art galleries and delicious dining.

Cruising and cookouts on Shelter Island

Tucked between the North and South Forks of Long Island, just a ten-minute ferry ride from adorable Sag Harbor, and a great choice for weekend rentals, Shelter Island offers a different side to the Hamptons. There’s still a party crowd to be found here, but the so-called scene is largely contained to Sunset Beach on the west coast. Elsewhere, the town’s sleepy ambiance comes courtesy of wildlife watching along the water trails, relaxed cruises in Gardiners Bay, and the open-to-all Wednesday night cookouts at the Gatsby-era Pridwin.