Southampton, NY, USA

Southampton, NY, USA

We found 1,865 vacation rentals — enter your dates for availability


Find the best place to stay — Southampton

Where to stay around Southampton, NY?

Our 2018 property listings offer a large selection of 1,865 vacation rentals near Southampton. From 1,575 houses to 113 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.

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.

Step back in time in Southampton

When you’re not sunning yourself on the beach, head to the town of Southampton where there are some great family-friendly attractions for you to enjoy. Be sure to visit the Southampton Historical Museum, which gives a superb insight into the history of the area. Comprising 12 buildings, including a blacksmith’s shop and a carpentry shop, the highlight is the beautifully restored 19th-century mansion house. Set in another historic building, the Southampton Arts Center provides fantastic exhibitions and events, covering everything from sculptures to live jazz. They also offer many kid-friendly events, making it ideal for families.

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.

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.