Find the best Town of Southold Town Hotels

"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! "

"Staff was excellent. "

"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!"

"Beautiful house and trip to stay in the North Fork. Hosts are incredible. Highly recommend!! "

"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"

"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "