The best rentals from the top sites, all in one place

We believe finding a vacation rental in Southold should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Southold

Vacation rentals in Southold

There are 170 vacation rentals near Southold for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Southold vacation, you can find 10% rentals under $200/night. Or if you are willing to splurge on a luxury vacation in Southold, there are 17 between $752 and $1,225/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 18 there are short term home and apartment rentals in Southold to fit your New York vacation needs. The most popular types of short-term rental homes in Southold are houses, private rooms and bed & breakfasts. Southold has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Southold vacation homes for your trip.

Home-types in Southold

Southold has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Southold:
- Oceanfront170 vacation rentals
- Beach170 vacation rentals
- House145 vacation rentals
- Private Room10 vacation rentals

Points of interests in Southold

Southold has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Southold:
- Sparkling Pointe: 2,634 vacation rentals
- Bedell Cellars: 2,634 vacation rentals
- Duck Walk Vineyards: 2,634 vacation rentals
- Kontokosta Winery: 2,634 vacation rentals
- Town Beach: 1,786 vacation rentals
- Goldsmith's Inlet Park: 720 vacation rentals
- The Tap Room at Corey Creek: 720 vacation rentals
- Wolf Preserve: 170 vacation rentals