Staying at a Southold, New York, vacation rental surrounds you in this charming community's historic excellence and natural coastal beauty. Here, you'll find a delightfully picturesque town enveloped by scenic beaches, recreation, vineyards, and museums. You're going to love it here.
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Yes, 16 of our Southold homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).
Browse dog-friendly homes >Yes. 28 of our Southold vacation rentals have internet access, so you can stay connected throughout your trip.
Browse homes with internet access >Absolutely. Our local Southold team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.
Learn more about Vacasa Premium Clean >We offer a series of family-friendly vacation rentals in Southold. This includes homes with enough space and bedrooms to house larger get-togethers as well as smaller cottages for more intimate travel.
We recommend reviewing your Southold vacation rental options to find the perfect lodging for your next family trip.
Southold is known for its rich history, with several historical landmarks and museums to explore, such as the Southold Historical Society Museum and the Custer Institute and Observatory, the oldest public observatory in the United States.
In terms of its economy, Southold is primarily driven by tourism, agriculture, and fishing. The town is home to several vineyards, wineries, local farmers' markets, and seafood restaurants that serve fresh seafood from the nearby waters.
Overall, Southold is a charming and peaceful town that offers a relaxed and laid-back lifestyle with plenty of opportunities to enjoy the area's natural beauty and local culture.
From pet-friendly accommodations to vacation rentals for families in Southold, we offer some of the best places to stay in the area. Ready to plan your next vacation to this unique New York community? We thought so. Get inspired by exploring your rental options in Southold.
