Find Romantic Hotels in Southold, NY

"The property was beautiful! The view was beautiful! Staff was very helpful and friendly. The only thing that would make it better would be some sort of convenience shop for forgotten essentials. For example medications.. toiletries etc.. my son ate something that disagreed with him and we could not get him a simple Tums to make him feel better. A hotel of this size normally has at least a small area to purchase these items. "

"My fiancé and I recently spent a few nights at this beautiful hotel by the water in Old Saybrook, and we couldn’t have asked for a more perfect getaway. From start to finish, everything was exceptional. The cleanliness throughout the property was flawless — every space felt fresh, spotless, and well cared for. It set the tone for a relaxing and worry-free stay. The amenities were fantastic. We especially enjoyed the spa and the cozy common areas where we could unwind together. Everything was thoughtfully designed to create a luxurious and peaceful atmosphere. The dining experience was another highlight. Every meal we had was delicious, with fresh ingredients, creative menus, and warm, attentive service. Whether it was breakfast with a view or a romantic dinner by candlelight, the setting made it all feel extra special. What truly made the experience unforgettable was the view. Being right on the water, we were treated to stunning sunrises and serene evenings. Sitting together on the balcony, watching the sunset over the water, was one of the most peaceful and memorable parts of our trip. This hotel offered the perfect mix of romance, comfort, and beauty. My fiancé and I left feeling refreshed, connected, and already dreaming of our next visit. Highly recommended for couples looking for a scenic and serene escape."

"Awesome "

"Best resort in the Hamptons / Long Island area! My family and I loved this resort before and after renovations- which are incredible. The staff is outstandingly well trained and so kind. We come to Shelter Island / North Fork annually so we love that The Pridwin has been renewed. "