Southold Vacation Rentals are Perfect for NY Residents

Long Island runs along the coast of New York as a barrier island and hot vacation destination for northeastern residents. With numerous villages on the island, it might be hard to choose just one. However, you might consider Southold vacation rentals. Southold North Fork rentals are located in the North Fork of Long Island, which is one of the most northern villages. From Southold beach house rentals, you can explore the entire island and its beaches.

The History of Southold North Fork Rentals


Southold was settled in the 1640s, and is considered the first English settlement on Long Island, though East Hampton was actually settled a year earlier. Surprisingly, many of the residents on the island came from New Haven Colony in Connecticut to settle in Southold. When you visit Southold North Fork rentals, you can learn more about the history of the early town, including its Dutch roots. Or consider Southold golf rentals for a convenient golf vacation with friends. Many rentals are located on the green for easy access.

Southold Beach House Rentals Close to Long Island Hamlets


Every day you can leave Southold house rentals to explore the villages and hamlets on the island. A short drive from Southold North Fork rentals are Greenport, Cutchogue, East Marion, and Fishers Island. Each of these hamlets will have beaches, boating, and water attractions to keep you and your family entertained for the day. Do not forget to bring your picnic lunch from Southold vacation rentals to enjoy a little meal in one of the local parks.

Southold Vacation Rentals by Souvenir Shops


Shopping near Southold vacation rentals is mostly filled with tourist souvenirs but every once in a while you can find some antiques, artist prints, and other treasures. If you can stay at Southold beach house rentals for a few weeks, you might take some of the ferries in the area to Connecticut or New York for a different flavor of shopping.

Check out additional vacation rentals on Long Island such as house rentals on Fire Island, Greenport Long Island rentals, or Long Beach Island house rental to find the perfect vacation home on the coast of New York.


Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Barns
Chalets
Cottages
Farmhouses
Homes
Boats
Bungalows
Cabins
Castles
Condos
Estates
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Southold: Houses, Cottages & More(91)

91 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 - 14 night minimum stay
        • 3 BR,
        • 1 BA,
        • Sleeps 6
          (9)
          2 - 3 night minimum stay
          • 3 BR,
          • 1 BA,
          • Sleeps 5
            Book it Now!
            • 3 BR,
            • 3 BA,
            • Sleeps 8
              2 - 7 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 7
                (30)
                3 - 7 night minimum stay
                • 4 BR,
                • 2 BA,
                • Sleeps 10
                  (3)
                  2 night minimum stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 6
                    1 Review
                    3 - 7 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 5
                      3 - 7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 8
                        Book it Now!
                        5 - 7 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 8
                          1 Review
                          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)
                                  2 night minimum stay
                                  • 2 BR,
                                  • 1 BA,
                                  • Sleeps 4
                                    (9)
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      1 Review
                                      Book it Now!
                                      3 night minimum stay
                                      • 1 BR,
                                      • 1 BA,
                                      • Sleeps 3
                                        2 Reviews
                                        Book it Now!
                                        2 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          Book it Now!
                                          3 - 7 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                            2 Reviews
                                            $490 - $821
                                            per night
                                            Book it Now!
                                            3 - 7 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                              2 - 3 night minimum stay
                                              • 2 BR,
                                              • 1 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                                (38)
                                                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!
                                                      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
                                                          5 - 7 night minimum stay
                                                          • 3 BR,
                                                          • 2 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 8
                                                            (3)
                                                            2 - 5 night minimum stay
                                                            • 2 BR,
                                                            • 1 BA,
                                                            • Sleeps 6
                                                              (14)
                                                              Advertisement