Southold, NY, USA

Southold, NY, USA

We found 1,488 holiday rentals — enter your dates for availability


Find the best place to stay — Southold

Where to stay around Southold?

Our 2018 accommodation listings offer a large selection of 1,488 holiday lettings near Southold. From 1,259 houses to 95 cottages, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Southold 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: 101 holiday homes
  • Saybrook Manor: 37 holiday homes
  • Barnes Landing: 44 holiday homes
  • Niantic: 30 holiday homes
  • Old Saybrook Center: 32 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 travelers, the most popular points of interest to stay near are:

  • Corey Creek Winery: 3,041 holiday lettings
  • Croteaux Vineyards: 3,023 holiday lettings
  • Southold Station: 2,986 holiday lettings
  • Horton Point Park: 2,969 holiday lettings
  • Osprey's Dominion: 3,055 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 1,259 houses in Southold. Our other popular types of Southold holiday rentals include:

  • Cottages: 95 self catering accommodations
  • Farmhouses: 32 self catering accommodations
  • Apartments: 24 self catering accommodations

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

Can I find a holiday accommodation with pool in Southold?

Yes, you can select your preferred holiday accommodation with pool among our 803 holiday homes with pool available in Southold. Please use our search bar to access the selection of holiday rentals available.

    Make a Holiday Rental House in Southold, Long Island Your Home Away From Home

    At the north-eastern tip of Long Island in the state of New York lies the peaceful town of Southold. The town has been a settlement since the 17th century and is steeped in American history. A Southold holiday rental house will offer spectacular sea views as well as the opportunity to experience a range of activities.

    Things to Do on Holiday to Southold, Long Island

    One of the main attractions of a Southold holiday is the beaches. The town has several unspoilt, sandy beaches that are perfect for sunbathing and swimming. Visitors can also enjoy a range of watersports such as sailing, windsurfing, fishing, jet skiing and water skiing. Other activities available in the town include bird watching, horse riding, cycling, golf and nature walks.

    Also worth a visit on a Southold holiday is the Southold Indian Museum. This building has a collection of artefacts pertaining to the tribes that inhabited the area for thousands of years. Visitors can view pottery relics, spear heads, Indian art, children’s toys and examples of the fishing methods used by these Indians.

    Places to Visit on Holiday to Southold, Long Island

    Approximately half an hour’s drive south-west of Southold is the town of Riverhead. Not only does the town offer paddle-boat cruises, beaches and parks, it is home to the Riverhead Raceway. This is a quarter-mile oval track which is now the only racing circuit on the whole of Long Island. Visitors can enjoy NASCAR, Enduro, demolition derby’s and monster trucks throughout the year at the venue.

    Also worth a visit in the town is the Hallockville Museum. The museum is a farm homestead that dates back to the 18th century. As well as the actual homestead itself there are a range of original outbuildings, a barn, old machinery and beautiful gardens.

    Weather in Southold, Long Island

    Long Island is blessed with warm, somewhat humid summers and cold winters. The warmest months of the year to go on a Southold holiday are June, July and August, when the temperature can reach as high as 28°C during the day. December and January are generally the coldest months with average daytime temperatures of 3°C. Snow can fall to an amount of 20 inches during the winter. Visitors should be aware that Southold and the rest of Long Island is susceptible to thunderstorms and mild hurricanes.

    Travel to Southold, Long Island Visitors on a Southold holiday will arrive at the Long Island MacArthur Airport (ISP) which is approximately 74 kilometres from the town. Operators that offer cheap, regular flights to the area include BMI, US Airways, British Airways, United Airlines and Continental Airlines. Travellers can depart from several UK airports such as London Heathrow (LHR), Gatwick (LGW), Aberdeen (ABZ), Manchester (MAN) and Birmingham (BHX).