Destination guide

Picturesque beauty and extravagance in Southampton

Southampton is often associated with luxury and old money, and that’s certainly true when booking Southampton vacation rentals. The properties here are stunning, and most feature a pool, should you ever tire of the breathtaking beaches and wish to enjoy a dip in privacy. A place that has long attracted writers and artists, it has plenty of cultural attractions to explore, such as the Shinnecock Nation Cultural Center and Museum. Then top it all off with a quaint town center, packed with great restaurants and quirky specialty shops, and you’ve got one unbeatable vacation destination.


See Southampton in style

Thanks to its superb coastal location, Southampton has tons of great activities. Charter a luxury yacht for your group or family and explore the coast of Long Island in style. There’s a whole range of trips on offer, from exploring the oceanfront homes to cruising around the beautiful islands. For Southampton vacation rentals that are perfect for some ‘me time,’ check out properties near the luxurious spas for some chilled pampering, or near the many golf courses, where you can work on your swing. If you’re looking to get the adrenaline pumping, look toward the sea for the wide variety of watersports.


Take full advantage of summer in Southampton

To get the full benefit of Southampton’s incredible beaches, it’s best to plan to visit during the summer months. From June through August, temperatures hover between the high 60s to high 70s; perfect for a refreshing and relaxing dip in the sea and for kicking back on the beach. Spring and fall are also solid choices, when the temperatures are that little bit milder. But if you find the water too cold, don’t worry, there are hundreds of Southampton vacation rentals that come with their own pool.

Natural features

Explore the breathtaking coast of Southampton

The picturesque, unspoiled beaches are just one of the many beautiful attractions when it comes to the landscape of Southampton. One of the best ways to experience the rich wildlife of the area is by taking a trip to Conscience Point Historic Site and Nature Walk. It’s open all year round, and as you walk through its gentle trails, you’ll be rewarded with beautiful panoramas across Peconic Bay. Around 60 acres of maritime grasslands and rugged, windswept dunes play host to a wide variety of flora and wildlife, including many species of birds like osprey and the American black duck.


How to get to and around Southampton

The nearest airport is in East Hampton, NY (HTO), located 9.4 mi (15.1 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 12.7 mi (20.5 km) away.

If you'd prefer to travel by train, you can make your way to Southampton Station.

Where to stay around Southampton?

Our 2019 property listings offer a large selection of 2,398 vacation rentals near Southampton. From 2,094 Houses to 133 Cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Southampton for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Southampton?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Southampton:

  • Amagansett Dunes: 75 vacation rentals
  • Pipes Cove: 51 vacation rentals
  • Clearwater Beach: 107 vacation rentals
  • Bay Point: 50 vacation rentals
  • Silver Beach: 46 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Southampton?

HomeAway offers a large selection of vacation rentals near lovely places in Southampton. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Cooper's Beach: 3,199 vacation rentals
  • Shinnecock Hills Golf Course: 2,234 vacation rentals
  • Our Lady of Poland Catholic Church: 3,223 vacation rentals
  • Shinnecock East County Park: 2,811 vacation rentals
  • Halsey House: 3,220 vacation rentals

But there are many other points of interest around Southampton listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Southampton?

Yes, of course. HomeAway has 2,094 Houses in Southampton. Our other popular types of vacation rentals in Southampton include:

  • Cottages: 133 rentals available
  • Condos/Apartments: 53 rentals available
  • Villas: 10 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Southampton?

Yes, you can select your preferred vacation rental with pool among our 1,525 vacation rentals with pool available in Southampton. Please use our search bar to access the selection of vacation rentals available.