Photo by Brian V. Rowe

Southold holiday lettings

We found 1,005 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 126 homes, 19 cottages and other holiday rentals in Southold to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, such as air conditioning and a TV. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

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  • All the privacy of home
    Enjoy full kitchens, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore the waterfront setting in Southold

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. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Southold

Are you looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Southold a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Raphael Winery (2.7 mi / 4.4 km)
  • Pindar Vineyards (3 mi / 4.9 km)
  • Bedell Cellars (3.3 mi / 5.3 km)
  • Greenport Carousel (4.2 mi / 6.8 km)
  • Peconic Bay Winery (4.2 mi / 6.8 km)
  • Kontokosta Winery (4.7 mi / 7.6 km)

Exploring the natural landscape of Southold

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Southold is a great spot to appreciate mother nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Crescent Beach (2.9 mi / 4.7 km)
  • Sunset Beach (3.2 mi / 5.2 km)
  • 67 Steps Beach (4.8 mi / 7.8 km)
  • Sag Harbor Marine Park (8.2 mi / 13.1 km)
  • Orient Beach State Park (9.5 mi / 15.2 km)
  • The Hamptons Beaches (11.6 mi / 18.6 km)

Transport to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.

If you prefer train travel, the main station is Southold Station.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Southold?

Houses are the most popular style of holiday rental in Southold, according to our data. Even if you've got a different idea about what you want, Vrbo has properties in loads of shapes and sizes. Filter our options to find your perfect fit.

How much does it cost to rent a holiday rental in Southold?

The average price for a holiday rental in Southold is based on a number of factors, like property type, length of stay and season. Whether you're thinking about a sprawling villa with space for the whole family or a cosy condo just enough for two, just add your dates of travel to discover stays with terrific value.

How much does it cost to rent a beach house in Southold?

The average price for a holiday rental by the beach in Southold will depend on when you're going and the style and size of property you're searching for. Find prices easily on Vrbo by entering your travel dates. Then use the handy filters to choose the number of bedrooms and amenities that you require, like air conditioning, WiFi and a pool.

What are popular rental amenities in Southold?

Some of the most popular rental amenities people search for in Southold are nearby museums, a garden and a sauna. Whether you're on a trip with family, friends or even pets, Vrbo holiday homes have the best amenities for beginning new traditions with the people you cherish the most.

What are the top attractions for families in Southold?

There are lots of wonderful things to do and see with the family in Southold, including:

  • 67 Steps Beach
  • Railroad Museum of Long Island
  • Trumans Beach

Can I find two-bedroom holiday rentals in Southold?

Take off with your loved ones and experience complete comfort and privacy in one of the 29 two-bedroom holiday homes Southold has to offer.

Are there holiday rentals with WiFi in Southold?

You can pick from 62 holiday rentals with WiFi in Southold. If you'd like to disconnect from daily life on your holiday, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How old do you have to be to rent a holiday rental in Southold?

We recommend you check with the Southold holiday rental you're looking at on Vrbo as age restrictions differ. However, it's normally 16, 18 or 21.

How long can I rent a holiday rental in Southold for?

The amount of time you can stay in a Southold holiday home for is up to the property. Just enter your dates of travel to view available options offering extended stays. They include everything you need to make your extended trip more enjoyable and comfortable, such as kitchens and air conditioning. Some holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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