Discover a selection of 1,000 vacation rentals in Southold, NY 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 private pools. Prices start at $207 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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Top rated rentals — Southold
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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, Vrbo 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, NY?

Our 2021 property listings offer a large selection of 766 vacation rentals around Southold. From 719 house rentals to 65 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Southold?

Yes, of course. Vrbo has 719 Houses in Southold. Our other popular types of vacation rentals in Southold include:

  • Cottages: 65 rentals available
  • Bungalows: 65 rentals available
  • Condos/Apartments: 23 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 298 vacation rentals with pool available in Southold. Please use our search bar to access the selection of vacation rentals available.