Shelter Island Heights Hotels with Swimming Pool

"Thank you for such a wonderful vocation! We enjoyed our stay, and would go back there again."

"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."

"Clean, modern and reasonably priced. Beds were comfortable and the shower was great"

"Very nice staff and great location "

"We loved our stay. It’s like a motel turned eco friendly resort. We had an upper corner room, which afforded us unobstructed views and privacy. The bed was so comfortable and the room was spacious—except for the bathroom. The bathroom needs vanity space! While the charm of this place is partly due to its being vintage, if I’m spending $800 a night I want a modern, spacious bathroom. "

"Excellent property & stay! "

"Beautiful views quiet "

"After Labor Day it’s very quiet and it feels like you have the resort all to yourself."

"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. "