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location Southold is highly rated for Wineries and Family-Friendly by 37 people

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Tonight May 23 - May 24
This weekend May 24 - May 26
Next weekend May 31 - Jun 2

Top 10 Hotels in Southold

See all 920 Properties in Southold

Estimated price for 1 night/2 adults

Shorecrest Bed and Breakfast

Shorecrest Bed and Breakfast

54300 County Route 48, Southold, NY
Shorecrest Bed and Breakfast
    3.5 out of 5.0
     
     

    Situated by the ocean, this bed & breakfast is within 3 mi (5 km) of Horton Point Park, The Old Field Vineyards, and Sparkling Pointe. 67 Steps Beach and Kontokosta ...

    $266 per night for 2 guests

    May 29 - May 30
    Southold Beach Motel

    Southold Beach Motel

    53250 North Road, Southold, NY
    Southold Beach Motel
      2.0 out of 5.0
       
       

      Nestled on the beach, this Southold motel is within 3 mi (5 km) of Horton Point Park and Sparkling Pointe. Railroad Museum of Long Island and East End Seaport ...

      $205 per night for 2 guests

      May 27 - May 28
      Heron Suites at Port of Egypt Marine

      Heron Suites at Port of Egypt Marine

      61600 Main Rd, Southold, NY
      Heron Suites at Port of Egypt Marine
        3.0 out of 5.0
         
         

        Situated near the beach, this condo resort is 0.5 mi (0.8 km) from The Old Field Vineyards and within 3 mi (5 km) of Railroad Museum of Long Island and Sparkling ...

        Heron Suites at Port of Egypt MarineGet Rates

        New Listing: Bay Haven Colonial Steps From Private Beach w/ Fireplace, Backyard Deck, Outdoor DiningGet Rates

        5 Star Home! Great Outside Yard

        5 Star Home! Great Outside Yard

        Southold, NY
        5 Star Home! Great Outside Yard
           
           

          Situated on the beach, this romantic vacation home is within 1 mi (2 km) of Croteaux Vineyards, Mattebella Vineyards, and Corey Creek Winery. Osprey's Dominion ...

          5 Star Home! Great Outside YardGet Rates

          Perfect Family Vacation Home! Charming Waterfront Property Close to Vineyards

          Perfect Family Vacation Home! Charming Waterfront Property Close to Vineyards

          Southold, NY
          Perfect Family Vacation Home! Charming Waterfront Property Close to Vineyards
             
             

            Situated on the beach, this vacation home is within 3 mi (5 km) of Croteaux Vineyards, Mattebella Vineyards, and Corey Creek Winery. Osprey's Dominion and Sparkling ...

            Perfect Family Vacation Home! Charming Waterfront Property Close to VineyardsGet Rates

            Quaint North Fork House, Close to Beaches and Vineyards

            Quaint North Fork House, Close to Beaches and Vineyards

            Southold, NY
            Quaint North Fork House, Close to Beaches and Vineyards
               
               

              Situated in Southold, this vacation home is within 3 mi (5 km) of Sparkling Pointe, Horton Point Park, and Goldsmith's Inlet Park. Mattebella Vineyards and Osprey's ...

              Quaint North Fork House, Close to Beaches and VineyardsGet Rates

              Relaxation in Wine Country - Luxury 3 Bedroom With Heated Pool

              Relaxation in Wine Country - Luxury 3 Bedroom With Heated Pool

              Southold, NY
              Relaxation in Wine Country - Luxury 3 Bedroom With Heated Pool
                 
                 

                Situated in Southold, this romantic vacation home is 1.1 mi (1.7 km) from The Old Field Vineyards and within 3 mi (5 km) of Sparkling Pointe and Horton Point ...

                Relaxation in Wine Country - Luxury 3 Bedroom With Heated PoolGet Rates

                Lovely Waterview Cottage in the Heart of Long Island Wine Country

                Lovely Waterview Cottage in the Heart of Long Island Wine Country

                Southold, NY
                Lovely Waterview Cottage in the Heart of Long Island Wine Country
                   
                   

                  Situated in Southold, this romantic property is within 3 mi (5 km) of Sparkling Pointe, Horton Point Park, and Goldsmith's Inlet Park. Mattebella Vineyards and ...

                  Lovely Waterview Cottage in the Heart of Long Island Wine CountryGet Rates

                  Walk to Founders Landing Beach, Vineyards, Restaurants all a few Minutes Away

                  Walk to Founders Landing Beach, Vineyards, Restaurants all a few Minutes Away

                  Southold, NY
                  Walk to Founders Landing Beach, Vineyards, Restaurants all a few Minutes Away
                     
                     

                    Situated in Southold, this historic vacation home is 0.9 mi (1.5 km) from The Old Field Vineyards and within 3 mi (5 km) of Sparkling Pointe and Mattebella Vineyards. ...

                    Walk to Founders Landing Beach, Vineyards, Restaurants all a few Minutes AwayGet Rates

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