Find 4 Star Hotels in Southold, NY from AED 1,178

"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."

"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "

"The staff was incredibly genuine and the property felt intimate and comfortable."

"We had a wonderful stay "

"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"

"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "

"Great hosts"

"We had a wonderful stay at Andrew's house! The pool, hot tub, yard, and poolhouse are meticulously maintained. My 2 children (ages 2 and 4) loved their time in the pool, playing on the large lawn, and using the hammock. The house itself has a full kitchen and laundry with a large dining table great for a family. The location was beautiful--very close to wineries and lots of farmstands. We drove about 12 minutes to Greenport for an excellent dinner. Andrew was very friendly and helpful. ...

"Our short trip to sag harbor was planned very last minute. Raymond was more the than happy to accommodate and left us a really nice goody bag to boot !! The house was newly renovated with all the expected amenities. Lots of sleeping quarters yet felt cozy. From the pool and pool house, the outdoor kitchen, “driving range” and gym there was something for everyone !! Raymond was a gracious host!"

"Beautiful views and lovely service "

"very comfortable stay. "