Find Vacation Homes in Town of Southold Town, NY from $306

You can find incredible Town of Southold Town vacation homes for all types of budgets: between $306 and $306 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.

If you are looking for a great deal on your vacation home in Town of Southold Town, consider visiting in , when prices are usually cheaper.

There are 222 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.

Begin by entering your trip dates to see what type of Town of Southold Town rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.

Booking Town of Southold Town vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.

When thinking about what you want in your Town of Southold Town rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Town of Southold Town along with your vacation property, into a Town of Southold Town vacation package.

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.