Destination guide

The waterfront setting of Southold is ready to explore

The area's wineries and monuments are just a few of the reasons to vacation in Southold. Renowned for its island views, beaches and gardens, this city welcomes all visitors. If you're looking for accommodations with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.


Activities and attractions in and around Southold

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Southold has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Sparkling Pointe (0.9 mi / 1.5 km)
  • Croteaux Vineyards (1.2 mi / 1.9 km)
  • Mattebella Vineyards (1.2 mi / 1.9 km)
  • The Old Field Vineyards (1.2 mi / 2 km)
  • Corey Creek Winery (1.4 mi / 2.2 km)
  • Osprey's Dominion (1.6 mi / 2.6 km)
Natural features

Exploring the natural features in Southold

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Southold. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Horton Point Park (2 mi / 3.2 km)
  • Goldsmith's Inlet Park (2.5 mi / 4 km)
  • Crescent Beach (3 mi / 4.8 km)
  • Sunset Beach (3.3 mi / 5.3 km)
  • Shell Beach (4.5 mi / 7.3 km)
  • Wades Beach (4.8 mi / 7.7 km)
How to get there

Transportation to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.6 mi (18.6 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 18.8 mi (30.2 km) away.

If you're traveling by train, the main station is Southold Station.

How many vacation rentals are available around Southold?

Our 2020 vacation rental listings offer a large selection of 650 house rentals around Southold. From 527 Houses to 69 Cottages, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Southold is on HomeAway.

What is the best area to stay when travelling to Southold?

Whether you're travelling 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 Southold:

  • East Hampton North: 307 vacation rentals
  • Village of East Hampton: 588 vacation rentals
  • Saybrook Manor: 35 vacation rentals
  • Remsenburg: 54 vacation rentals
  • Lion Head Beach: 60 vacation rentals

For other neighbourhoods, 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 travelling to Southold?

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

  • Corey Creek Winery: 2,969 home rentals
  • Sparkling Pointe: 2,948 home rentals
  • Osprey's Dominion: 2,992 home rentals
  • Mattebella Vineyards: 2,968 home rentals
  • Horton Point Park: 2,895 home rentals

But there are many other points of interest around Southold 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 Southold?

Yes, of course. HomeAway has 527 Houses in Southold. Our other popular types of vacation rentals in Southold include:

  • Cottages: 69 lodging choices
  • Bungalows: 69 lodging choices
  • Condos/Apartments: 20 lodging choices

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

Can I find a vacation rental with pool in Southold?

Yes, you can select your preferred vacation rental with pool among our 256 vacation homes with pool available in Southold.

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