Southold, NY, USA

Southold, NY, USA

We found 1,537 vacation rentals — enter your dates for availability


Find the best place to stay — Southold

Where to stay around Southold?

Our 2018 property listings offer a large selection of 1,537 vacation rentals near Southold. From 1,294 houses to 96 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: 36 vacation rentals
  • Clearwater Beach: 105 vacation rentals
  • Amagansett Dunes: 75 vacation rentals
  • Saybrook Manor: 38 vacation rentals
  • Old Saybrook Center: 29 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: 3,141 vacation rentals
  • Croteaux Vineyards: 3,137 vacation rentals
  • Sparkling Pointe: 3,105 vacation rentals
  • Horton Point Park: 3,095 vacation rentals
  • Osprey's Dominion: 3,174 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 1,294 houses in Southold. Our other popular types of vacation rentals in Southold include:

  • Cottages: 96 rentals available
  • Farmhouses: 33 rentals available
  • Apartments: 27 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 rentals in Southold?

Absolutely, HomeAway has 801 golf rentals in Southold. You have also many other possibilities in Southold area, including:

  • Near the ocean rentals: 365 rentals
  • Beach rentals: 244 rentals
  • Waterfront rentals: 189 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 817 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.