Where to stay near Southold?

Our 2020 accommodation listings offer a large selection of 651 holiday rentals near Southold. From 599 Houses to 63 Cottages, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Southold for a long holiday or a weekend break is on HomeAway.

What is the best area to stay when travelling to Southold?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday rentals for a long holiday or just a weekend break in Southold:

  • Westbrook Center: 57 holiday homes
  • East Hampton North: 279 holiday homes
  • Clearwater Beach: 93 holiday homes
  • Saybrook Manor: 32 holiday homes
  • Beach Hampton: 47 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes available.

What are the most popular points of interest and landmarks to stay near when travelling to Southold? offers a large selection of holiday homes near great places in Southold. From travellers, the most popular points of interest to stay near are:

  • Sparkling Pointe: 2,591 holiday rentals
  • Osprey's Dominion: 2,632 holiday rentals
  • Southold Station: 2,577 holiday rentals
  • Croteaux Vineyards: 2,607 holiday rentals
  • Mattebella Vineyards: 2,610 holiday rentals

But there are many other points of interest around Southold listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Southold?

Yes, of course. offers 599 Houses in Southold. Our other popular types of Southold holiday rentals include:

  • Cottages: 63 holiday houses
  • Bungalows: 63 holiday houses
  • Condos/Apartments: 24 holiday houses

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

Can I find a holiday accommodation with pool in Southold?

Yes, you can select your preferred holiday accommodation with pool among our 258 holiday homes with pool available in Southold. Please use our search bar to access the selection of holiday rentals available.

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