Where to stay around Southold?

Our 2018 accommodation listings offer a large selection of 716 holiday lettings near Southold. From 566 Houses to 86 Cabins, find unique self catering accommodation 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 accommodations for a long holiday or just a weekend break in Southold:

  • Clearwater Beach: 95 holiday homes
  • Barnes Landing: 41 holiday homes
  • Saybrook Manor: 35 holiday homes
  • Niantic: 145 holiday homes
  • Old Saybrook Center: 28 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Southold?

HomeAway offers a large selection of holiday accommodations near great places in Southold. From HomeAway travellers, the most popular points of interest to stay near are:

  • Corey Creek Winery: 3,096 holiday lettings
  • Croteaux Vineyards: 3,076 holiday lettings
  • Osprey's Dominion: 3,111 holiday lettings
  • Southold Station: 3,037 holiday lettings
  • Horton Point Park: 3,023 holiday lettings

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 holiday rentals available near the point of interest of your choice.

Can I rent Houses in Southold?

Yes, of course. HomeAway offers 566 Houses in Southold. Our other popular types of Southold holiday rentals include:

  • Cabins: 86 self catering accommodations
  • Cottages: 86 self catering accommodations
  • Bungalows: 86 self catering accommodations

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

Can I find a holiday accommodation with pool in Southold?

Yes, you can select your preferred holiday accommodation with pool among our 245 holiday homes with pool available in Southold. Please use our search bar to access the selection of holiday rentals available.

    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, 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 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)

    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)