Southold vacation rentals

We found 1,004 vacation 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 vacation rentals in Southold to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Explore the waterfront setting in Southold

The area's wineries and monuments are just a few of the reasons to vacation in 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 hoping to discover things to do in the city? Venture out of your vacation home and experience everything that makes Southold a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Southold. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.

If you'd prefer to travel by train, you can make your way to Southold Station.

Frequently asked questions

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

Houses are the most popular style of vacation 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 vacation rental in Southold?

The average price for a vacation 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 cozy 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 vacation 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 vacation 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 vacation rentals in Southold?

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

Are there vacation rentals with WiFi in Southold?

You can pick from 62 vacation rentals with WiFi in Southold. If you'd like to disconnect from daily life on your vacation, 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 vacation rental in Southold?

We recommend you check with the Southold vacation 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 vacation rental in Southold for?

The amount of time you can stay in a Southold vacation 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 vacation homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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