Find the best Town of Southold Town Hotels

"Rented the cottage for my wife, 1.5 year old, and myself, Andrew was fantastic and easy to get in contact with for all questions/concerns. The cottage, grounds, pool, and hot tub are well maintained and we had a great experience overall. Will be planning another stay here! "

"Many people from our large wedding party stayed at the Cliffside condominiums for two nights. The facilities were excellent. Beautiful beach and nice clean two bedroom two bath condos."

"Feels like a remote vacation destination just a couple of hours from home. Self-contained property with private beach and pool away from crowds and tourists, but close to town."

"Superb in every way!"

"Convenient and close to everything! "

"The hotel was lovely"

"Staff was excellent. "

"Our stay in Greenport at the Sandpiper was wonderful! Location was perfect: easy walk into town and to the ferry to shelter island. Ten out of ten!"

"We’ve stayed at several properties in the Greenport area and this was our first time at Silver Sands; we loved it! The rooms were updated, clean and cute. The beach access was a huge plus, as well as on site restaurants. They don’t charge for parking (as some hotels nearby are starting to do) and the location is central to Greenport Village and the wineries. We went for an anniversary trip and stayed in the motel section but would definitely come back with the kids and try out the bungalows! Overall great trip and would recommend to others; we will be back!"