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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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  • Showing 1-50 of 300+
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    Exceptional! 5.0/5
    (9 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 5
    Cottage #707484vb
    9
    Viewed 7 times in the last 48 hours
      Wonderful! 4.9/5
      (17 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 5
      Estate #718247vb
      17
      Viewed 8 times in the last 48 hours
        • 4 BR
        • 4 BA
        • Sleeps 8
        House #722609vb
        5
          • 4 BR
          • 3 BA
          • Separate Toilet
          • Sleeps 10
          House #722961vb
            Exceptional! 5.0/5
            (30 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 10
            House #648890vb
            30
            Viewed 22 times in the last 48 hours
              Wonderful! 4.8/5
              (24 reviews)
              avg/night
              • 4 BR
              • 1 BA
              • Sleeps 7
              House #973167
              24
              Viewed 10 times in the last 48 hours
                • 4 BR
                • 1 BA
                • Sleeps 7
                House #421606vb
                24
                  Exceptional! 5.0/5
                  (6 reviews)
                  avg/night
                  • 4 BR
                  • 2 BA
                  • Sleeps 9
                  Cottage #4113414
                  6
                    • 4 BR
                    • 2 BA
                    • Sleeps 10
                    House #575273vb
                    6
                      Exceptional! 5.0/5
                      (59 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      Apartment #246865
                      59
                      Viewed 11 times in the last 48 hours
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Studio #4049919
                        3
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          House #321313vb
                          1 Review
                          Viewed 15 times in the last 48 hours
                            Exceptional! 5.0/5
                            (26 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 6
                            House #401305vb
                            26
                              Wonderful! 4.9/5
                              (11 reviews)
                              avg/night
                              • 3 BR
                              • 1 BA
                              • Sleeps 6
                              Cottage #731486vb
                              11
                              Viewed 25 times in the last 48 hours
                                • 3 BR
                                • 2 BA
                                • Sleeps 4
                                Cottage #3953729
                                13
                                  Exceptional! 5.0/5
                                  (32 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  House #559448vb
                                  32
                                  Viewed 23 times in the last 48 hours
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 10
                                    House #906820vb
                                      Wonderful! 4.9/5
                                      (33 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Separate Toilet
                                      • Sleeps 6
                                      Apartment #563575vb
                                      33
                                      Viewed 14 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (19 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        Bungalow #804815vb
                                        19
                                        Viewed 5 times in the last 48 hours
                                          avg/night
                                          • 8 BR
                                          • 7 BA
                                          • Separate Toilet
                                          • Sleeps 15
                                          House #4159462
                                          3
                                          Viewed 8 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (11 reviews)
                                            avg/night
                                            • 3 BR
                                            • 1 BA
                                            • Separate Toilet
                                            • Sleeps 6
                                            Cottage #797161vb
                                            11
                                            Viewed 7 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (23 reviews)
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              House #3789275
                                              23
                                              Viewed 21 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (16 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 9
                                                House #622236vb
                                                16
                                                Viewed 33 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (5 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                  House #3925407
                                                  5
                                                  Viewed 34 times in the last 48 hours
                                                    • 4 BR
                                                    • 3 BA
                                                    • Separate Toilet
                                                    • Sleeps 10
                                                    House #4113898
                                                    3
                                                      Wonderful! 4.9/5
                                                      (15 reviews)
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                                                      • 5 BR
                                                      • 2 BA
                                                      • Sleeps 12
                                                      House #3981190
                                                      15
                                                      Viewed 9 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
                                                          (25 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Cottage #723865vb
                                                          25
                                                          Viewed 7 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (11 reviews)
                                                            avg/night
                                                            • 5 BR
                                                            • 3 BA
                                                            • Sleeps 14
                                                            Farmhouse #810873vb
                                                            11
                                                            Viewed 26 times in the last 48 hours
                                                              Excellent! 4.7/5
                                                              (19 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Apartment #711062vb
                                                              19
                                                              Viewed 6 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (16 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                Apartment #716707vb
                                                                16
                                                                Viewed 5 times in the last 48 hours
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 7
                                                                  Bungalow #488661vb
                                                                  4
                                                                    Wonderful! 4.9/5
                                                                    (14 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 5
                                                                    House #3554393
                                                                    14
                                                                    Viewed 29 times in the last 48 hours
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                      House #860859vb
                                                                      Viewed 14 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (9 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                        House #3950429
                                                                        9
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Separate Toilet
                                                                          • Sleeps 6
                                                                          House #750517vb
                                                                          5
                                                                            Exceptional! 5.0/5
                                                                            (6 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 14
                                                                            House #821199vb
                                                                            6
                                                                            Viewed 12 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (19 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Apartment #997722
                                                                              19
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 9
                                                                                House #4212692
                                                                                1 Review
                                                                                Viewed 14 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (14 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Condo #607936vb
                                                                                  14
                                                                                  Viewed 12 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
                                                                                      • Sleeps 6
                                                                                      House #587577vb
                                                                                      5
                                                                                        Excellent! 4.6/5
                                                                                        (7 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Separate Toilet
                                                                                        • Sleeps 8
                                                                                        House #3621885
                                                                                        7
                                                                                        Viewed 8 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 1 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 8
                                                                                          House #856356vb
                                                                                          3
                                                                                          Viewed 23 times in the last 48 hours
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Separate Toilet
                                                                                            • Sleeps 6
                                                                                            Farmhouse #875221vb
                                                                                            2 Reviews
                                                                                            Viewed 18 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
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                Chateau / Country House #318061vb
                                                                                                23
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  Farmhouse #864192vb
                                                                                                  2 Reviews
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 5
                                                                                                    House #255932vb
                                                                                                    6
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    Terrific weekend getaway

                                                                                                    5 of 5
                                                                                                    We spent a lovely weekend at this home. Loved the nearby restaurants, the quick walk to the beach, and of course the property itself. It was a beautifully restored place, very roomy,, and the pictures don't do it justice. The location is peaceful and charming. We thoroughly enjoyed our short stay and would definitely return.
                                                                                                    • Review Submitted: 08-Oct-2009
                                                                                                    • Date of Stay: Sep 2009