Where to stay around Southold, NY?

Our 2018 property listings offer a large selection of 782 vacation rentals near Southold. From 620 Houses to 88 Cabins, 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 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:

  • Clearwater Beach: 95 vacation rentals
  • Niantic: 108 vacation rentals
  • Old Saybrook Center: 29 vacation rentals
  • Westbrook Center: 52 vacation rentals
  • Madison Center: 36 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:

  • Mattebella Vineyards: 3,157 vacation rentals
  • Osprey's Dominion: 3,188 vacation rentals
  • Southold Station: 3,114 vacation rentals
  • Croteaux Vineyards: 3,152 vacation rentals
  • Horton Point Park: 3,110 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 620 Houses in Southold. Our other popular types of vacation rentals in Southold include:

  • Cabins: 88 rentals available
  • Cottages: 88 rentals available
  • Bungalows: 88 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Southold?

Yes, you can select your prefered vacation rental with pool among our 270 vacation rentals with pool available in Southold. Please use our search bar to access the selection of vacation rentals available.

    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)

    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)