Where to stay around Southold?

Our 2018 property listings offer a large selection of 1,605 vacation rentals near Southold. From 1,366 houses to 105 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 HomeAway.

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:

  • Niantic: 35 vacation rentals
  • Clearwater Beach: 107 vacation rentals
  • Amagansett Dunes: 79 vacation rentals
  • Saybrook Manor: 37 vacation rentals
  • Old Saybrook Center: 27 vacation rentals

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

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

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

  • Goldsmith's Inlet Park: 3,198 vacation rentals
  • Croteaux Vineyards: 3,208 vacation rentals
  • Sparkling Pointe: 3,186 vacation rentals
  • Horton Point Park: 3,200 vacation rentals
  • Corey Creek Winery: 3,223 vacation rentals

But there are many other points of interest around Southold listed on HomeAway 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. HomeAway has 1,366 houses in Southold. Our other popular types of vacation rentals in Southold include:

  • Cottages: 105 rentals available
  • Farmhouses: 30 rentals available
  • Apartments: 28 rentals available

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

Can I rent golf resort rentals in Southold?

Absolutely, HomeAway has 802 golf resort rentals in Southold. You have also many other possibilities in Southold area, including:

  • Near the ocean rentals: 368 rentals
  • Beach rentals: 245 rentals
  • Waterfront rentals: 185 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Southold?

Yes, you can select your preferred vacation rental with pool among our 857 vacation rentals with pool available in Southold. Please use our search bar to access the selection of vacation rentals available.

    Take in the Waterfront Beauty of Southold

    The beaches, gardens and island views display a scene truly unique to Southold. This family-friendly city is known for its wineries, dancing and football. Whether you're planning a family vacation, friends trip or romantic retreat, consider a rental home. Many rentals come with a full kitchen and separate dining area.

    Attractions In and Around Southold

    First time in Southold and looking for places to see? Take the kids and check out Shelter Island Tennis Club, Harbes Family Farm and Long Island Aquarium and Exhibition Center. To appreciate the outdoor scene, make time for beaches like Crescent Beach and Sunset Beach and green spaces such as Horton Point Park and Goldsmith's Inlet Park. Want to take in a game or event? Get tickets for Riverhead Raceway. Fun activities in the city include Sparkling Pointe, Croteaux Vineyards and Mattebella Vineyards. Also while in town, consider a visit to The Old Field Vineyards and Osprey's Dominion.