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Destination guide

The waterfront setting of Southold is ready to explore

The area's wineries and monuments are just some of the reasons to come on holiday to Southold. Renowned for its island views, beaches and gardens, this city welcomes all visitors. If you're looking for accommodation options 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

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 holiday 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 centre:

  • 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 holiday in Southold. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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

Transport to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.6 mi (18.6 km) from the city centre. 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 travelling by train, the main station is Southold Station.

How many holiday rentals are available around Southold?

Our 2020 accommodation listings offer a large selection of 655 holiday lettings around Southold. From 21 flats & apartments to 62 bungalows, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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:

  • East Hampton North: 297 holiday homes
  • Westbrook Center: 67 holiday homes
  • Niantic: 159 holiday homes
  • Madison Center: 39 holiday homes
  • Clearwater Beach: 96 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.co.uk offers a large selection of holiday accommodations near great places in Southold. From HomeAway.co.uk travellers, the most popular points of interest to stay near are:

  • Southold Station: 2,839 holiday lettings
  • Croteaux Vineyards: 2,872 holiday lettings
  • Osprey's Dominion: 2,898 holiday lettings
  • Mattebella Vineyards: 2,875 holiday lettings
  • The Old Field Vineyards: 2,827 holiday lettings

But there are many other points of interest around Southold listed on HomeAway.co.uk 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 Flats in Southold?

Yes, of course. HomeAway.co.uk offers 21 Flats in Southold. Our other popular types of Southold holiday rentals include:

  • Bungalows: 62 self catering accommodations
  • Houses: 544 self catering accommodations
  • Cottages: 62 self catering accommodations

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

Can I find a holiday accommodation with pool in Southold?

Yes, you can select your preferred holiday accommodation with pool among our 261 holiday homes with pool available in Southold. Please use our search bar to access the selection of holiday rentals available.