Discover a selection of 500 holiday rentals in Southold, NY, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 216 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 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, 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 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.

Can I find a vacation rental around Southold?

Yes, our 2021 property listings offer a large selection of 706 vacation rentals near Southold. From 662 houses to 59 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Southold for a holiday or a weekend are on Vrbo.

What are the popular points of interest near where I can stay when traveling to Southold?

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

  • Southold Station: 2,731 vacation rentals
  • Croteaux Vineyards: 2,763 vacation rentals
  • Osprey's Dominion: 2,787 vacation rentals
  • Mattebella Vineyards: 2,767 vacation rentals
  • The Old Field Vineyards: 2,715 vacation rentals

But there are many other points of interest around Southold listed on Vrbo UK 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 UK has 662 Houses in Southold. Our other popular types of vacation rentals in Southold include:

  • Cottages: 59 rentals available
  • Bungalows: 59 rentals available
  • Flats: 21 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 279 vacation rentals with pool available in Southold. Please use our search bar to access the selection of vacation rentals available.