Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

Pick from Southold Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Frequently asked questions

What is there to see and do in Southold?

Take in the natural beauty with a stop at Horton Lane Beach. Discover sights such as Sparkling Pointe, Croteaux Vineyards, and Sannino’s Bella Vita Vineyard during your stay.

When is the best time to book a hotel with a pool in Southold?

You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Southold in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.

What's the best way to travel around Southold?

Knowing the transportation options in Southold can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, ride aboard one of the trains from Southold Station. Southold might not have many public transit options to choose from so consider renting a car to explore more.