Discover a selection of 500 vacation rentals in Southold that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $340 per night, and houses and cottages are popular options for a stay in Southold. Either way, you'll find a rental for everyone's needs.
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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

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 property listings offer a large selection of 672 vacation rentals around Southold. From 556 house rentals to 67 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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

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 Southold:

  • East Hampton North: 297 vacation rentals
  • Clearwater Beach: 96 vacation rentals
  • Westbrook Center: 67 vacation rentals
  • Niantic: 159 vacation rentals
  • Remsenburg: 45 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Southold?

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

  • Croteaux Vineyards: 2,872 vacation rentals
  • The Old Field Vineyards: 2,827 vacation rentals
  • Osprey's Dominion: 2,898 vacation rentals
  • Sparkling Pointe: 2,860 vacation rentals
  • Southold Station: 2,839 vacation rentals

But there are many other points of interest around Southold listed on Vrbo 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. Vrbo has 556 Houses in Southold. Our other popular types of vacation rentals in Southold include:

  • Cottages: 67 rentals available
  • Condos/Apartments: 17 rentals available
  • Bungalows: 67 rentals available

But you can also enjoy a great stay in one of our other vacation rentals 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 269 vacation rentals with pool available in Southold. Please use our search bar to access the selection of vacation rentals available.

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