Search Holiday Rentals in Town of Southold Town

"Beautiful "

"Great "

"This is a lovely motel located right on the Sound and all rooms face the water. The room was clean and relatively spacious, though most of the space was devoted to the kitchen and living areas. The bathroom was a bit small, as was the sleeping area. My family, including an elderly relative, traveled here for a family wedding in mid-April. The wedding was initially set to begin at 3:30 PM; check-in time is 4:00 PM. When I tried to arrange an earlier check-in time in advance, I was told that I would just have to take my chances because the motel was unwilling to guarantee an early check-in unless I also stayed the night before the wedding or paid a high hourly fee (i.e., roughly 1/3 of the room rate per hour of early check-in). Given that a significant percentage of the overnight guests were there for the wedding, and that one of the four rooms I reserved was for an elderly relative of the couple, I was taken aback by the motel management's rigidity. Fortunately, the couple was able to push back the time of the ceremony to accommodate their guests because the motel would not do so."

"This is my third time at the Cliffside, and as always it was a lovely space that was great value for money. The only reason I didn’t give it five stars was that the heat was wildly inconsistent: in the small bedroom it was very hot, and the kitchen/living room, cool, and in the master bedroom, frigid. Otherwise, great. "

"Great location! Very clean! "

"Tara was wonderful and helpful at check-in, the cleaning staff was so nice and thorough, and the food at Nookies and the Boathouse were both amazing!! "

"Kaylee, John and the rest of the staff were helpful and patient. We felt like we were home. My daughter and I will definitely be back here to stay. We took many pictures and videos and will tell everyone about our stay here. Having a Galley on each floor was helpful as we had everything we needed within reach. Two suggestions, maybe get a peep hole for the room doors and have a microwave in each Galley so we don’t have to ask staff to microwave anything. Other than that, we felt relaxed and staying here made our trip just perfect. Little touches such as warm breakfast croissants, the candy bar (we seriously ate so many jellybeans and m&m’s this trip lol), the game room/bar area, macaroons upon checkout….we never felt rushed or like we were a bother. Can’t say enough about our experience here. Thank you, Thank you, Thank you!"

"Location was perfect for visiting the wineries… breakfast was to die for!"

"amazing stay! "