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 highlights

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)

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.

Where to stay around Southold?

Our 2019 accommodation listings offer a large selection of 793 holiday lettings near Southold. From 647 Houses to 79 Cottages, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Southold is on HomeAway.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Southold:

  • Barnes Landing: 53 holiday homes
  • Niantic: 421 holiday homes
  • East Hampton North: 382 holiday homes
  • Village of East Hampton: 716 holiday homes
  • Old Saybrook Center: 23 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Southold?

HomeAway offers a large selection of holiday accommodations near great places in Southold. From HomeAway travellers, the most popular points of interest to stay near are:

  • Osprey's Dominion: 3,635 holiday lettings
  • Corey Creek Winery: 3,626 holiday lettings
  • Mattebella Vineyards: 3,610 holiday lettings
  • Horton Point Park: 3,546 holiday lettings
  • Croteaux Vineyards: 3,610 holiday lettings

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 holiday rentals available near the point of interest of your choice.

Can I rent Houses in Southold?

Yes, of course. HomeAway offers 647 Houses in Southold. Our other popular types of Southold holiday rentals include:

  • Cottages: 79 self catering accommodations
  • Bungalows: 79 self catering accommodations
  • Condos/Apartments: 26 self catering accommodations

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

Can I find a holiday accommodation with pool in Southold?

Yes, you can select your preferred holiday accommodation with pool among our 306 holiday homes with pool available in Southold. Please use our search bar to access the selection of holiday rentals available.

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