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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Southold holiday rentals

Beach nearby
Cliffside Resort Condominiums

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southold Hotel Reviews

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"Great sta"
Brandon 2-night trip
Posted 2 days ago
The Shoals Suites and Slips

Find out more about Southold

Holiday Rentals in Southold

Search for holiday rentals in Southold on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Southold using one of the methods below:

  • View our selection of featured holiday rentals in Southold
  • Use the map to find apartments and other holiday homes in the Southold neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southold while they last

Look no further and take a look at our great range of rental properties in Southold!

Frequently asked questions

Can I find a holiday rental in Southold?

Yes, there are holiday rentals in Southold close to Custer Institute and Observatory, or you can select a more secluded option if you're looking for a relaxing stay. Southold is known for its wineries and beaches. Make sure you have time to check out the gardens and football games during your trip.

How many holiday rentals are there in Southold?

With 119 Expedia holiday rentals, you're guaranteed to find just the right place for your Southold stay.

What’s there to see and do in Southold?

McCabe's Beach and Horton Lane Beach are a couple of lovely local spots to get outside and enjoy nature. While here, Sparkling Pointe and The Old Field Vineyards are other places worth a visit.

What’s a holiday rental in Southold like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Southold. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.