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Make a Holiday Rental House in Southold, Long Island Your Home Away From Home

At the north-eastern tip of Long Island in the state of New York lies the peaceful town of Southold. The town has been a settlement since the 17th century and is steeped in American history. A Southold holiday rental house will offer spectacular sea views as well as the opportunity to experience a range of activities.

Things to Do on Holiday to Southold, Long Island

One of the main attractions of a Southold holiday is the beaches. The town has several unspoilt, sandy beaches that are perfect for sunbathing and swimming. Visitors can also enjoy a range of watersports such as sailing, windsurfing, fishing, jet skiing and water skiing. Other activities available in the town include bird watching, horse riding, cycling, golf and nature walks.

Also worth a visit on a Southold holiday is the Southold Indian Museum. This building has a collection of artefacts pertaining to the tribes that inhabited the area for thousands of years. Visitors can view pottery relics, spear heads, Indian art, children’s toys and examples of the fishing methods used by these Indians.

Places to Visit on Holiday to Southold, Long Island

Approximately half an hour’s drive south-west of Southold is the town of Riverhead. Not only does the town offer paddle-boat cruises, beaches and parks, it is home to the Riverhead Raceway. This is a quarter-mile oval track which is now the only racing circuit on the whole of Long Island. Visitors can enjoy NASCAR, Enduro, demolition derby’s and monster trucks throughout the year at the venue.

Also worth a visit in the town is the Hallockville Museum. The museum is a farm homestead that dates back to the 18th century. As well as the actual homestead itself there are a range of original outbuildings, a barn, old machinery and beautiful gardens.

Weather in Southold, Long Island

Long Island is blessed with warm, somewhat humid summers and cold winters. The warmest months of the year to go on a Southold holiday are June, July and August, when the temperature can reach as high as 28°C during the day. December and January are generally the coldest months with average daytime temperatures of 3°C. Snow can fall to an amount of 20 inches during the winter. Visitors should be aware that Southold and the rest of Long Island is susceptible to thunderstorms and mild hurricanes.

Travel to Southold, Long Island Visitors on a Southold holiday will arrive at the Long Island MacArthur Airport (ISP) which is approximately 74 kilometres from the town. Operators that offer cheap, regular flights to the area include BMI, US Airways, British Airways, United Airlines and Continental Airlines. Travellers can depart from several UK airports such as London Heathrow (LHR), Gatwick (LGW), Aberdeen (ABZ), Manchester (MAN) and Birmingham (BHX).

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  • 1 - 50 of 300+
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    Exceptional! 5.0/5
    (30 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 10
    House #648890vb
    30
    Viewed 44 times in the last 48 hours
      • 4 BR
      • 2 BA
      • Sleeps 10
      House #575273vb
      6
        avg/night
        • 4 BR
        • 3 BA
        • Sleeps 10
        House #906820vb
        Viewed 5 times in the last 48 hours
          avg/night
          • 4 BR
          • 3 BA
          • Separate Toilet
          • Sleeps 10
          House #4113898
          3
          Viewed 6 times in the last 48 hours
            Wonderful! 4.8/5
            (19 reviews)
            avg/night
            • 3 BR
            • 1 BA
            • Sleeps 5
            Cottage #285350vb
            19
            Viewed 19 times in the last 48 hours
              Exceptional! 5.0/5
              (6 reviews)
              avg/night
              • 4 BR
              • 3 BA
              • Sleeps 14
              House #821199vb
              6
              Viewed 20 times in the last 48 hours
                avg/night
                • 4 BR
                • 2 BA
                • Sleeps 9
                House #4212692
                1
                Viewed 20 times in the last 48 hours
                  Excellent! 4.7/5
                  (9 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 4
                  House #57035vb
                  9
                    • 3 BR
                    • 2 BA
                    • Separate Toilet
                    • Sleeps 6
                    Farmhouse #875221vb
                    2
                    Viewed 17 times in the last 48 hours
                      Exceptional! 5.0/5
                      (6 reviews)
                      avg/night
                      • 4 BR
                      • 2 BA
                      • Sleeps 10
                      House #340957
                      6
                      Viewed 10 times in the last 48 hours
                        • 2 BR
                        • 1 BA
                        • Separate Toilet
                        • Sleeps 5
                        House #255932vb
                        6
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 7
                          House #7092717
                          1
                          Viewed 7 times in the last 48 hours
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                            Cottage #3791124
                            7
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              House #4157754
                              Viewed 5 times in the last 48 hours
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 5
                                House #4023369
                                2
                                Viewed 7 times in the last 48 hours
                                  • 4 BR
                                  • 4 BA
                                  • Sleeps 10
                                  House #4039006
                                    Exceptional! 5.0/5
                                    (10 reviews)
                                    avg/night
                                    • 5 BR
                                    • 2 BA
                                    • Sleeps 10
                                    House #647972vb
                                    10
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 6
                                      House #987257
                                      5
                                        Wonderful! 4.8/5
                                        (6 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        House #482861vb
                                        6
                                          avg/night
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 8
                                          House #4199496
                                          Viewed 13 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (35 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Cottage #966043
                                            35
                                            Viewed 20 times in the last 48 hours
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 11
                                              House #574911vb
                                              13
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 8
                                                House #869467vb
                                                  avg/night
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 10
                                                  Cottage #896250vb
                                                  1
                                                  Viewed 7 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (50 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Separate Toilet
                                                    • Sleeps 6
                                                    Cottage #304995
                                                    50
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 5
                                                      House #867310vb
                                                      1
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Cottage #3561038
                                                        6
                                                          Exceptional! 5.0/5
                                                          (10 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Cottage #488565vb
                                                          10
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 9
                                                            House #4214226
                                                            1
                                                              Wonderful! 4.8/5
                                                              (5 reviews)
                                                              avg/night
                                                              • 5 BR
                                                              • 4 BA
                                                              • Separate Toilet
                                                              • Sleeps 10
                                                              House #601247vb
                                                              5
                                                              Viewed 6 times in the last 48 hours
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 6
                                                                House #4154502
                                                                1
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Cottage #870640vb
                                                                  Viewed 9 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (19 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    House #281433
                                                                    19
                                                                    Viewed 26 times in the last 48 hours
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      House #368762vb
                                                                      7
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        Cottage #365948vb
                                                                        11
                                                                          • 5 BR
                                                                          • 3 BA
                                                                          • Sleeps 7
                                                                          House #860141vb
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 5
                                                                            House #862295vb
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 12
                                                                              House #962919vb
                                                                              Viewed 10 times in the last 48 hours
                                                                                • 4 BR
                                                                                • 3 BA
                                                                                • Separate Toilet
                                                                                • Sleeps 8
                                                                                House #286118vb
                                                                                3
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Separate Toilet
                                                                                  • Sleeps 8
                                                                                  House #397434vb
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 8
                                                                                    House #106308vb
                                                                                    1
                                                                                    Viewed 12 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (64 reviews)
                                                                                      avg/night
                                                                                      • 5 BR
                                                                                      • 5 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 12
                                                                                      House #256774vb
                                                                                      64
                                                                                      Viewed 8 times in the last 48 hours
                                                                                        avg/night
                                                                                        • 7 BR
                                                                                        • 4 BA
                                                                                        • Sleeps 22
                                                                                        House #823805vb
                                                                                        Viewed 50 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Cottage #869140vb
                                                                                          4
                                                                                          Viewed 10 times in the last 48 hours
                                                                                            Excellent! 4.6/5
                                                                                            (20 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 6
                                                                                            House #238066
                                                                                            20
                                                                                            Viewed 7 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (22 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 4 BA
                                                                                              • Separate Toilet
                                                                                              • Sleeps 10
                                                                                              House #694143vb
                                                                                              22
                                                                                              Viewed 28 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (19 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 6
                                                                                                House #902109
                                                                                                19
                                                                                                Viewed 26 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (16 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  House #619892vb
                                                                                                  16
                                                                                                  Viewed 38 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (24 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 7
                                                                                                    House #973167
                                                                                                    24
                                                                                                    Viewed 18 times in the last 48 hours
                                                                                                      • 4 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 7
                                                                                                      House #421606vb
                                                                                                      24
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