Find the best Town of Southold Town Hotels

"Great view of the water and nice amenities with the beach and pool."

"Great little boutique hotel. Staff were very helpful and accommodating. Great restaurants and wineries in the area. Would highly recommend!"

"The property was clean beautiful and pleasant. Loved the trendy decor."

"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."

"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "

"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"

"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"

"Two mid age couples just had a good and relaxing time with great hospitality. "

"Mark and Mona were great hosts. The house and grounds were beautiful. Southold is a great town to explore and the house is close to the beach and the town. We loved the use of the bicycles which made our trip much more fun. We could ride to the beach, the town, and the wineries. Mona even pumped my bike tires before we went to explore. Thanks for a great time and we hope to be back again next year !"

"very comfortable stay. "

"This was the perfect, in town place to stay for the two of us. Located on a quiet street of well-maintained homes, and with parking right outside, it was a short 1-1/2 block walk to all the shops, restaurants, ferry, docks, etc. The apt is small, but clean and tidy, sun-filled and air-conditioned. We loved staying here and will again in the future."

"John communicated well with clear directions. His book of local suggestions were helpful and we loved the location - walking/biking distance to all the action! Loved Greenport!"

"extra clean brand new rooms. bathroom door did lock by itself and the small hole on the plate outside did unlock it when depressed otherwise perfect. we had 2 under 3 kids and the way it was set up was safe and fun"