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South Shore Vacations

Pack those stellar shades. We have South Shore 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 South Shore – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with South Shore 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 South Shore

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 South Shore 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 South Shore well.

Top Hotel Deals

See all 23 Hotels in South Shore
Days Inn by Wyndham Ashland

Days Inn by Wyndham Ashland

12700 Route 180, Ashland
    2.0 out of 5.0
     
     

    Situated in Ashland, this hotel is 1.3 mi (2.1 km) from KYOVA Tri-State Mall and within 6 mi (10 km) of Sandy Creek Golf Course and Armco Park. Diamond Links ...

    Days Inn by Wyndham Ashland$57

    Days Inn by Wyndham Ashland$57
    Carter Caves State Resort Park

    Carter Caves State Resort Park

    344 Caveland Dr, Olive Hill
      2.5 out of 5.0
       
       

      Situated in a state park, this hotel is steps from Carter Caves State Park and Carter Caves State Park Golf Course. Bat Cave and Cascade Caverns is 0.8 mi (1.3 ...

      Knights Inn Ashland

      Knights Inn Ashland

      7216 Sr 60, Ashland
        1.5 out of 5.0
         
         

        Situated in Ashland, this motel is 1.1 mi (1.8 km) from Armco Park and 1.9 mi (3 km) from KYOVA Tri-State Mall. Sandy Creek Golf Course and Sundowner Golf Course ...

        Knights Inn Ashland$51

        Knights Inn Ashland$51
        Super 8 by Wyndham Grayson

        Super 8 by Wyndham Grayson

        125 Super Eight Ln, Grayson
          2.0 out of 5.0
           
           

          Situated in Grayson, this hotel is 0.2 mi (0.3 km) from Kentucky Christian University and 12 mi (19.3 km) from Hidden Cove Golf Course. KYOVA Tri-State Mall ...

          Super 8 by Wyndham Grayson$64

          Super 8 by Wyndham Grayson$64
          Holiday Inn Express & Suites Ashland

          Holiday Inn Express & Suites Ashland

          13131 Slone Court, Ashland
            2.5 out of 5.0
             
             

            Situated in Ashland, this hotel is 1.5 mi (2.4 km) from KYOVA Tri-State Mall and within 6 mi (10 km) of Sandy Creek Golf Course and Armco Park. Paramount Arts ...

            Holiday Inn Express & Suites Ashland$89

            Holiday Inn Express & Suites Ashland$89
            Quality Inn and Suites

            Quality Inn and Suites

            501 CW Stevens Blvd, Grayson
              2.5 out of 5.0
               
               

              Situated in Grayson, this hotel is 0.8 mi (1.4 km) from Kentucky Christian University and within 20 mi (32 km) of KYOVA Tri-State Mall and Hidden Cove Golf Course. ...

              Quality Inn and Suites$84

              Quality Inn and Suites$84
              Fairfield Inn & Suites By Marriott Ashland

              Fairfield Inn & Suites By Marriott Ashland

              10945 Route 60, Ashland
                2.5 out of 5.0
                 
                 

                Situated in Ashland, this hotel is 0.5 mi (0.8 km) from KYOVA Tri-State Mall and within 6 mi (10 km) of Sandy Creek Golf Course and Armco Park. Paramount Arts ...

                Fairfield Inn & Suites By Marriott Ashland$84

                Fairfield Inn & Suites By Marriott Ashland$84
                Holiday Inn Portsmouth Downtown

                Holiday Inn Portsmouth Downtown

                711 2nd St, Portsmouth
                  3.0 out of 5.0
                   
                   

                  Situated in Portsmouth, this hotel is 0.4 mi (0.6 km) from Shawnee State University and within 6 mi (10 km) of Philip Moore Jr. Stone House and Earl Thomas Conley ...

                  Holiday Inn Portsmouth Downtown$146

                  Holiday Inn Portsmouth Downtown$146
                  Greenbo Lake State Resort Park

                  Greenbo Lake State Resort Park

                  965 Lodge Rd, Argillite
                     
                     

                    Situated in Argillite, this lodge is close to Greenbo Lake State Resort Park. Regional attractions also include KYOVA Tri-State Mall and Ashland Town ...

                    Holiday Inn Express & Suites Ironton

                    Holiday Inn Express & Suites Ironton

                    401 South 9th Street, Ironton
                      2.5 out of 5.0
                       
                       

                      Situated in Ironton, this hotel is 1.1 mi (1.8 km) from Ohio University Southern Campus and within 6 mi (10 km) of Paramount Arts Center and Pendleton Art Center. ...

                      Holiday Inn Express & Suites Ironton$113

                      Holiday Inn Express & Suites Ironton$113

                      Top Flight Deals

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