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Southold Waterfront Vacation Rentals Vacation Rentals(26)

26 Results
Book it Now!
1 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
    (6)
    2 night minimum stay
    • 4 BR,
    • 2 BA,
    • Sleeps 8
      (16)
      2 - 3 night minimum stay
      • 3 BR,
      • 1 BA,
      • Sleeps 5
        $429 - $929
        per night
        7 - 11 night minimum stay
        • 4 BR,
        • 2 BA,
        • 2 HF BA,
        • Sleeps 14
          3 - 7 night minimum stay
          • 4 BR,
          • 2 BA,
          • Sleeps 10
            (3)
            3 - 7 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 8
              Book it Now!
              3 - 5 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
                (4)
                2 night minimum stay
                • 2 BR,
                • 1 BA,
                • Sleeps 4
                  (7)
                  Book it Now!
                  5 - 7 night minimum stay
                  • 3 BR,
                  • 3 BA,
                  • Sleeps 8
                    1 Review
                    Book it Now!
                    2 - 3 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 4
                      (9)
                      3 - 7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 8
                        (12)
                        $175 - $200
                        per night
                        2 night minimum stay
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 4
                          (4)
                          2 - 3 night minimum stay
                          • 5 BR,
                          • 5 BA,
                          • 1 HF BA,
                          • Sleeps 12
                            (73)
                            2 - 7 night minimum stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 6
                              (6)
                              14 - 31 night minimum stay
                              • 3 BR,
                              • 3 BA,
                              • Sleeps 8
                                3 - 7 night minimum stay
                                • 5 BR,
                                • 2 BA,
                                • Sleeps 6
                                  3 - 7 night minimum stay
                                  • 4 BR,
                                  • 2 BA,
                                  • 2 HF BA,
                                  • Sleeps 8
                                    7 more choices from the HomeAway Network
                                    2 - 7 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 10
                                      (23)
                                      $300 - $307
                                      per night
                                      2 - 6 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 7
                                        (3)
                                        5 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          (3)
                                          3 - 30 night minimum stay
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 8
                                            (8)
                                            • 6 BR,
                                            • 5 BA,
                                            • Sleeps 12
                                              7 - 30 night minimum stay
                                              • 4 BR,
                                              • 3 BA,
                                              • Sleeps 8
                                                3 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 8
                                                  (10)
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                                                  Recent Southold Reviews

                                                  BEST DECISION EVER!

                                                  5 of 5
                                                  My husband and I rented this cottage for most of the summer and couldn't be happier with it. We lovingly refer to this place as The Pond Shack. The house is small and rustic so if you want a luxurious rental, this isn't for you. But if you want a low key retreat at an unbeatable price in an absolutely gorgeous location with beautiful views of the Great Pond (it's really more of a lake) and a 5 minute walk to the beach, then look no further. This place is perfect for 2 couples or a couple with kids. The pond is clean and not scummy - great for swimming or just watching the water. The best thing about this place is that you feel totally in nature. We've seen a ton of Osprey, swallows, a cardinal and of course geese and there's even a swan that lives on the pond too. There are also turtles in the pond, and deer and rabbits all around the neighborhood. There are great walking/running trails just up the street and of course gorgeous Kenney's Beach with uninterrupted sound-front stretches of sand (and rocks too - bring aqua socks if you have them!). We like to walk over and watch the sunset and the water is calm and great for swimming. The owner Larry is great and we've enjoyed meeting him and interacting with him throughout our stay. He's always been very friendly, responsive and helpful. We love the North Fork and couldn't be happier to have found this gem. So sad the summer's almost over but we will definitely be back!
                                                  • Submitted: Aug 17, 2014
                                                  • Stayed: May 2014

                                                  Great for big family

                                                  5 of 5
                                                  Loved the cottage, location and how close the beach was for swimming and kayaking. The best was that the older children could sleep in the studio and we didn't have to listen to their TV shows and they could sleep late without being disturbed. We'll be back.
                                                  • Submitted: Aug 9, 2014
                                                  • Stayed: Jul 2014

                                                  delightful and relaxing getaway

                                                  5 of 5
                                                  My friends and I enjoyed a wonderful long weekend at the cottage on the lake. We loved the well-stocked, spacious kitchen and the beautiful and peaceful surroundings. Judith and Yehudit were incredibly thoughtful and helpful during and even after our stay. After I forgot my memory foam pillow there, they brought back to the city for me and worked to ensure that it was easy for me to retrieve. The cottage had everything we needed, including even good books, bikes, and a humongous pot for our lobster boil. We enjoyed cooked, exploring nearby beaches, and visiting the many vineyards that were within minutes by bike. I highly recommend this rental and I look forward to staying there again soon!
                                                  • Submitted: Jul 21, 2014
                                                  • Stayed: May 2014