Search Vacation Homes in Southold

"I found it cozy, comfortable and very peaceful. Bonus wildlife visits of deer, geese and turkeys, Most people will understand this accommodation as quality “clamping”."

"Pretty gingerbread cottage, well appointed. Lovely area, 2 min walk to the beach. Owners super helpful. Overall beautiful, serene, highly recommmend."

"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."

"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"

"This was a great house! Everythingwas perfect, the house was very clean and David was incredibly accomodating to all our requests and provifed great recommendations for places to visit. We will definitely be back"

"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"

"Great stuff, loved the house!"

"Perfect spot for a weekend on the North Fork"

"Very nice place. Would definitely stay there again (actually this our second stay at the property). Clean, well equipped and the pictures are accurate."

"Great stay and wonderful property. The first stay that didn’t have a book and list full of restrictions and checkout instructions. After a whirlwind weekend celebrating our daughter ‘s engagement, this was a welcomed surprise! Everyone enjoyed their stay, including our two labs. Great fenced in yard that gave them plenty of room to exercise. We will be back!"

"Our group of four friends in our 50s loved our stay here. Heather was a responsive, welcoming, flexible host who left us a card, bottle of wine and a prepped wood pile in the fire pit. The decor was tasteful and beautiful, clean and modern. The mattresses were firm, which we liked. We made use of the comfortable couch on the deck as well as the gas fireplace in the living room. The location is lovely and we had a short, 5-minute walk to the beach. Birders would enjoy the tremendous diversity of...

"We had an amazing time at this house! My family all came back to Long Island to attend my fathers memorial service nearby and this house had all the details and comforts to make the weekend as enjoyable as possible...and the view is AMAZING! I would definitely recommend this location and would stay there again!"

"We loved this property. It’s open floor plan made it a great gathering place. Great location, clean and comfortable. Highly recommend"

"This cottage is Comfortable, clean and fully stocked on a private street with a beautiful short walk to the beach. We were only 2 but house could easily sleep up to 8 guests. Large backyard with tranquil outdoor setting firepit and Barbeque. Host is very responsive welcoming and helpful. The nearby Main street has many restaurants and shops as well as Wine vineyards. Will definitely be booking again in future. We found a new love and that is Jamesport. Thank you Kelly!"

"This was such a cute place. We visited in spring where everything is just start to bloom the yard was fenced in so great for dogs, with a cute play place for kids. The neighborhood is so quiet and peaceful. We walked several of the streets and meet a few friendly neighbors. The host was fantastic checking in to make sure we had everything we needed. The house was clean, Air with lots of windows and light. We spent time playing board games and reconnect. Definitely would come the area again and...

"This property was just what my family and I were looking for. A quaint and quiet house with a small town feel. We stayed for NYE hoping to get away from the loud chaos we’re typically faced with at home and this location fit the bill. Pros: I’m not sure how this changes in the summer months but things were mostly quiet. There are restaurants, coffee, and food shopping all within a 5 minute drive. The home itself is pretty small, so for the 4 of us- husband, 17y/o, 9 y/o, and myself, it was...

"Beautiful home, very neat and organized."

"It was lovely having my family stay at Jackie's home for a family wedding in Greenport. The home accommodated our large group and was a close walk to town as well! Jackie was communicative when we needed prior to reservation and we would recommend this stay to anyone who is looking for a lovely time in Greenport!"

"The cottage is a perfect cozy stay on the water - we stayed in the winter and still were able to enjoy the sand and the sunrises right outside the window. House is well-appointed and well-located within area with access to restaurants and shops in Clinton, Madison, Westbrook, Old Saybrook, etc."

"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."

"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."

"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."

"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "