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Southold Vacation Rentals(52)

52 Results
Book it Now!
1 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
    (6)
    2 - 14 night minimum stay
    • 5 BR,
    • 4 BA,
    • Sleeps 10
      (10)
      2 night minimum stay
      • 4 BR,
      • 2 BA,
      • Sleeps 8
        (17)
        2 - 7 night minimum stay
        • 3 BR,
        • 2 BA,
        • Sleeps 7
          (30)
          3 - 7 night minimum stay
          • 4 BR,
          • 2 BA,
          • Sleeps 10
            (3)
            Book it Now!
            3 - 5 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 6
              (4)
              3 - 7 night minimum stay
              • 2 BR,
              • 1 BA,
              • Sleeps 4
                (6)
                7 night minimum stay
                • 4 BR,
                • 2 BA,
                • Sleeps 8
                  (13)
                  2 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 6
                    (7)
                    Book it Now!
                    3 - 7 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 6
                      2 Reviews
                      Book it Now!
                      3 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 3
                        2 Reviews
                        $490 - $821
                        per night
                        Book it Now!
                        3 - 7 night minimum stay
                        • 4 BR,
                        • 3 BA,
                        • Sleeps 8
                          Book it Now!
                          5 - 7 night minimum stay
                          • 3 BR,
                          • 3 BA,
                          • Sleeps 8
                            1 Review
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                            • 3 BR,
                            • 3 BA,
                            • Sleeps 8
                              2 - 3 night minimum stay
                              • 2 BR,
                              • 1 BA,
                              • 1 HF BA,
                              • Sleeps 6
                                (39)
                                Book it Now!
                                2 - 3 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 4
                                  (9)
                                  Book it Now!
                                  2 - 3 night minimum stay
                                  • 2 BR,
                                  • 1 BA,
                                  • Sleeps 4
                                    (3)
                                    Book it Now!
                                    7 - 14 night minimum stay
                                    • 4 BR,
                                    • 3 BA,
                                    • Sleeps 6
                                      2 Reviews
                                      Book it Now!
                                      2 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                        Book it Now!
                                        3 night minimum stay
                                        • 5 BR,
                                        • 4 BA,
                                        • Sleeps 4
                                          $300 - $350
                                          per night
                                          Book it Now!
                                          3 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 8
                                            3 - 7 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                              (13)
                                              5 - 7 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 8
                                                (3)
                                                2 night minimum stay
                                                • 2 BR,
                                                • 1 BA,
                                                • Sleeps 4
                                                  (7)
                                                  2 - 7 night minimum stay
                                                  • 4 BR,
                                                  • 3 BA,
                                                  • Sleeps 13
                                                    (5)
                                                    2 night minimum stay
                                                    • 2 BR,
                                                    • 1 BA,
                                                    • Sleeps 4
                                                      (10)
                                                      $386 - $600
                                                      per night
                                                      2 - 7 night minimum stay
                                                      • 4 BR,
                                                      • 2 BA,
                                                      • Sleeps 8
                                                        (5)
                                                        2 - 7 night minimum stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                          (3)
                                                          $2,450 - $3,500
                                                          per week
                                                          7 night minimum stay
                                                          • 3 BR,
                                                          • 3 BA,
                                                          • Sleeps 8
                                                            (3)
                                                            $175 - $200
                                                            per night
                                                            2 night minimum stay
                                                            • 1 BR,
                                                            • 1 BA,
                                                            • Sleeps 4
                                                              (4)
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                                                              Recent Southold Reviews

                                                              Our fourth time here and we still love it!

                                                              5 of 5
                                                              We returned to the Cabin on the Pond for our fourth year and it continues to be a highlight of our summer. With each visit we discover more of the North Fork by riding their bikes to nearby wineries, beaches and restaurants. We also spent so much time around the cabin relaxing on the hammock, fishing and BBQing. As always, the cabin was clean and fully equipped with everything we might need. Using the Cabin’s paddleboat, canoe and kayak we spent hours on the lake. The fishing in Great Pond is surprisingly good with small & large mouth bass, chain pickerel, perch sunfish and more. This year the weather was perfect for walking down to nearby Kenny’s beach and getting some sun. Some of our favorite destinations nearby: Briarmere farms for pie Braun’s seafood to pick up fresh oysters Grana for pizza Vineyards: Lenz, Mattebella, Shinn (Mainly for the friendly service, pretty atmosphere and lack of crowds) We’re looking forward to our 5th year!
                                                              • Submitted: Sep 19, 2014
                                                              • Stayed: Aug 2014

                                                              Exceptional

                                                              5 of 5
                                                              The property was located on a wooded lot, alongside a wide creek, with a floating dock and access onto Peconic Bay. In a short drive we could reach multiple beaches, Greenport, vineyards and a plethora of restaurants. The house was large with spacious rooms, furnished comfortably and fully equipped so that we could entertain as many as 10 guests. The property was well maintained and clean. The owner was pleasant and helpful. This was a 5 star vacation.
                                                              • Submitted: Sep 14, 2014
                                                              • Stayed: Aug 2014

                                                              cute rustic cottage with great location

                                                              5 of 5
                                                              My husband and I stayed here for Labor Day weekend, and were thrilled with the cottage. It was the perfect space for 2 people (although you could squeeze an extra 2 in on the sofabed if you're really desperate). We loved the old hardwood floors and quaint details, and the location was great: 10 min. walk to Kenney's Beach, and within a 10 min. drive to many of the local farms and wineries. The kitchen was fully stocked, including a big pot and kitchen shears for cooking lobsters, and a grill with direct gas line. We enjoyed cooking our farm fresh ingredients there most nights. There were plenty of towels, but bring your own hair dryer. We were so sad to leave, and would definitely consider renting here again.
                                                              • Submitted: Sep 2, 2014
                                                              • Stayed: Aug 2014