Find Hotels with a Pool in Southold, NY

The Shoals Suites and Slips: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Water’s Edge Resort & Spa: Features an indoor pool, an outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Hotel, 2-minute walk from The Hamptons Beaches. Offers spa services, a seasonal outdoor pool, and a snack bar/deli. Hyatt Place Long Island East End: Features a seasonal outdoor pool, an indoor pool, and 2 hot tubs. Baron’s Cove: Offers 2 outdoor pools, an indoor pool, and a full-service spa.

Take in the natural beauty with a stop at Horton Lane Beach. Discover sights such as Sparkling Pointe, The Old Field Vineyards, and Corey Creek Winery during your stay.

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.

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.