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Winchester Vacations

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

Hotwire can help you find your travel bliss with Winchester 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 Winchester

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 Winchester 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 Winchester well.

Top Hotel Deals

See all 16 Hotels in Winchester
French Quarter Inn

French Quarter Inn

25 East McDonald Parkway, Maysville
    3.0 out of 5.0
     
     

    Situated in Maysville, this hotel is within a 10-minute walk of Russell Theatre, Kentucky Gateway Museum Center, and National Underground Railroad Museum. Washington ...

    Super 8 by Wyndham Maysville KY

    Super 8 by Wyndham Maysville KY

    550 Tucker Dr, Maysville
      2.0 out of 5.0
       
       

      Situated in Maysville, this hotel is within 2 mi (3 km) of Washington Visitors Center, Laurel Oaks Golf Club, and Kenton Station Golf Course. National Underground ...

      Super 8 by Wyndham Maysville KY$69

      Super 8 by Wyndham Maysville KY$69
      Hampton Inn Maysville

      Hampton Inn Maysville

      503 Marketplace Dr, Maysville
         
         

        Situated in Maysville, this hotel is within 3 mi (5 km) of Washington Visitors Center, Kenton Station Golf Course, and Laurel Oaks Golf Club. National Underground ...

        Days Inn by Wyndham Hillsboro

        Days Inn by Wyndham Hillsboro

        103 Harry Sauner Rd, Hillsboro
          2.5 out of 5.0
           
           

          Situated in a rural location, this aparthotel is 1.9 mi (3.1 km) from Highland County Courthouse and within 9 mi (15 km) of Hillsboro Elks Country Club and Rocky ...

          Countryside Inn & Suites

          Countryside Inn & Suites

          100 Leininger Street, Mount Orab
            2.5 out of 5.0
             
             

            Situated in Mount Orab, this hotel is within 20 mi (32 km) of Elks Run Golf Course, The Golf Club at Stonelick Hills, and Tri-State Warbird Museum. EastGate ...

            Countryside Inn & Suites$102

            Countryside Inn & Suites$102
            Brown's Motel Aberdeen

            Brown's Motel Aberdeen

            1055 US HWY 52, Aberdeen
              2.0 out of 5.0
               
               

              Situated in Aberdeen, this motel is within 2 mi (3 km) of Russell Theatre, National Underground Railroad Museum, and Kentucky Gateway Museum Center. Kenton Station ...

              Quality Inn

              Quality Inn

              1428A US 68, Maysville
                2.0 out of 5.0
                 
                 

                Located in the heart of Maysville, this motel is within 3 mi (5 km) of Washington Visitors Center, Kenton Station Golf Course, and National Underground Railroad ...

                Comfort Inn Seaman

                Comfort Inn Seaman

                55 Stern Dr, Seaman
                  2.5 out of 5.0
                   
                   

                  Situated in Seaman, this hotel is within 25 mi (40 km) of Serpent Mound, Highland County Courthouse, and Hillsboro Elks Country Club. Rocky Fork Lake State Park ...

                  Greystone Motel

                  Greystone Motel

                  8190 US Highway 50, Hillsboro
                    2.5 out of 5.0
                     
                     

                    Situated in Hillsboro, this motel is 1.4 mi (2.2 km) from Highland County Courthouse and 2.6 mi (4.1 km) from Hillsboro Elks Country Club. Rocky Fork Lake State ...

                    Ammen Home Bed, Breakfast and Retreat

                    Ammen Home Bed, Breakfast and Retreat

                    115 S. Apple Street, Georgetown
                      3.0 out of 5.0
                       
                       

                      This bed & breakfast is in Georgetown.

                      Top Flight Deals

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