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Southold Vacations

Pack those stellar shades. We have Southold vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Southold – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Southold vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Southold

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Southold vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Southold well.

Southold Flight + Hotel packages

Top Hotel Deals

See all 241 Hotels in Southold
Heron Suites at Port of Egypt Marine

Heron Suites at Port of Egypt Marine

61600 Main Rd, Southold
    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 ...

    Southold Beach Motel

    Southold Beach Motel

    53250 North Road, Southold
      2.0 out of 5.0
       
       

      Nestled on the beach, this Southold motel is within 3 mi (5 km) of Horton Point Park, The Old Field Vineyards, and Sparkling Pointe. 67 Steps Beach and Norman ...

      Shorecrest Bed and Breakfast

      Shorecrest Bed and Breakfast

      54300 County Route 48, Southold
        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. Kontokosta Winery and ...

        The Atlantic Hotel

        The Atlantic Hotel

        1655 County Road 39, Southampton
          2.5 out of 5.0
           
           

          Situated by the ocean, this hotel is 1 mi (1.7 km) from Shinnecock Hills Golf Course and within 3 mi (5 km) of Shinnecock Nation Cultural Center and Museum and ...

          The Atlantic Hotel$127

          The Atlantic Hotel$127
          Greenview Inn Riverhead

          Greenview Inn Riverhead

          1433 W Main St, Riverhead
            2.0 out of 5.0
             
             

            Located in the heart of Riverhead, this motel is within 2 mi (3 km) of Riverhead Raceway, Tanger Outlet Center, and Out East Family Fun. Safari Adventure and ...

            Greenview Inn Riverhead$79

            Greenview Inn Riverhead$79
            Water's Edge Resort & Spa

            Water's Edge Resort & Spa

            1525 Boston Post Road, Westbrook
              3.5 out of 5.0
               
               

              This Westbrook resort is on the beach, 1.7 mi (2.8 km) from Tanger Outlets, and within 6 mi (10 km) of Harvey's Beach and Indian River Marina. General William ...

              Water's Edge Resort & Spa $210

              Water's Edge Resort & Spa $210
              Hampton Maid Motel

              Hampton Maid Motel

              259 E Montauk Hwy, Southampton
                2.5 out of 5.0
                 
                 

                Situated near the beach in Hampton Bays, this motel is close to Meschutt Beach, Shinnecock Hills Golf Course and Shinnecock East County Park. Area attractions ...

                Topping Rose House

                Topping Rose House

                One Bridgehampton - Sag Harbor Turnpike, Southampton
                  4.5 out of 5.0
                   
                   

                  Situated in Bridgehampton, this luxury hotel is within a 15-minute walk of South Fork Natural History Museum and Nature Center and Children's Museum of The East ...

                  Hilton Garden Inn Riverhead

                  Hilton Garden Inn Riverhead

                  2038 Old Country Rd, Riverhead
                    3.0 out of 5.0
                     
                     

                    Located in the heart of Riverhead, this hotel is within a 15-minute walk of Tanger Outlet Center and Riverhead Raceway. Out East Family Fun and Splish Splash ...

                    Hilton Garden Inn Riverhead$139

                    Hilton Garden Inn Riverhead$139
                    Southampton Inn

                    Southampton Inn

                    91 Hill Street, Southampton
                      3.0 out of 5.0
                       
                       

                      This family-friendly Southampton hotel is located by the ocean, within a 5-minute walk of Agawam Park and Southampton Cultural Center. Southampton Historical ...

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.