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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 42 Properties in Winchester
Best Western Inn

Best Western Inn

1602 Dinah Shore Boulevard, Winchester
    2.5 out of 5.0
     
     

    Situated in Winchester, this hotel is 6.3 mi (10.1 km) from Cowan Railroad Museum and 8.5 mi (13.7 km) from Elk River Dam. University of the South and Lake Cheston ...

    Best Western Inn$76

    Best Western Inn$76
    The Smokehouse Lodge and Cabins

    The Smokehouse Lodge and Cabins

    844 W Main Street, Monteagle
      3.0 out of 5.0
       
       

      Situated on a lake, this hotel is within 6 mi (10 km) of Sewanee Golf and Tennis Club, University of the South, and Lake Cheston.

      The Smokehouse Lodge and Cabins$70

      The Smokehouse Lodge and Cabins$70
      Microtel Inn & Suites by Wyndham Manchester

      Microtel Inn & Suites by Wyndham Manchester

      201 Expressway Dr, Manchester
        2.0 out of 5.0
         
         

        Situated in Manchester, this hotel is 1.7 mi (2.7 km) from Great Stage Park and within 20 mi (32 km) of Elk River Dam and George Dickel Distillery. Black House ...

        Microtel Inn & Suites by Wyndham Manchester$51

        Microtel Inn & Suites by Wyndham Manchester$51
        Baymont by Wyndham Tullahoma

        Baymont by Wyndham Tullahoma

        2113 N Jackson St, Tullahoma
          2.5 out of 5.0
           
           

          Situated in Tullahoma, this hotel is 4.6 mi (7.4 km) from George Dickel Distillery and within 16 mi (25 km) of Elk River Dam and Jack Daniel's Distillery. Calsonic ...

          Baymont by Wyndham Tullahoma$67

          Baymont by Wyndham Tullahoma$67
          Red Roof Inn & Suites Manchester, TN

          Red Roof Inn & Suites Manchester, TN

          126 Expressway Drive, Manchester
            2.0 out of 5.0
             
             

            Situated in Manchester, this hotel is 1.6 mi (2.5 km) from Great Stage Park and within 20 mi (32 km) of Elk River Dam and George Dickel Distillery. Black House ...

            Red Roof Inn & Suites Manchester, TN$64

            Red Roof Inn & Suites Manchester, TN$64
            Sleep Inn And Suites Manchester

            Sleep Inn And Suites Manchester

            84 Relco Drive, Manchester
              2.5 out of 5.0
               
               

              Located in the heart of Manchester, this hotel is 1.3 mi (2.2 km) from Great Stage Park and within 25 mi (40 km) of Elk River Dam and George Dickel Distillery. ...

              Sleep Inn And Suites Manchester$99

              Sleep Inn And Suites Manchester$99
              Super 8 by Wyndham Monteagle TN

              Super 8 by Wyndham Monteagle TN

              713 W Main St, Monteagle
                2.0 out of 5.0
                 
                 

                Situated in Monteagle, this hotel is within 6 mi (10 km) of Sewanee Golf and Tennis Club, University of the South, and Lake Cheston. Cowan Railroad Museum is ...

                Super 8 by Wyndham Monteagle TN$59

                Super 8 by Wyndham Monteagle TN$59
                Hampton Inn Fayetteville

                Hampton Inn Fayetteville

                110 Redstone Dr, Fayetteville
                  2.5 out of 5.0
                   
                   

                  Situated in Fayetteville, this hotel is 1.2 mi (2 km) from Fayetteville Lincoln County Museum and 3.4 mi (5.5 km) from Fayetteville Golf and Country. Jack Daniel's ...

                  Hampton Inn Fayetteville$88

                  Hampton Inn Fayetteville$88
                  Quality Inn & Suites

                  Quality Inn & Suites

                  1156 Highway 28, Jasper
                    2.5 out of 5.0
                     
                     

                    Situated in a rural location, this hotel is 0.6 mi (1 km) from Grandview Medical Center and 2.8 mi (4.5 km) from Jasper City Park. Marion County Park is 6.3 ...

                    Quality Inn & Suites$81

                    Quality Inn & Suites$81
                    Hampton Inn Kimball

                    Hampton Inn Kimball

                    100 Hampton Drive, Kimball
                      2.5 out of 5.0
                       
                       

                      Situated in Kimball, this hotel is within 9 mi (15 km) of Grandview Medical Center, Jasper City Park, and Bridgeport Depot Museum. Marion County Park is 9 mi ...

                      Hampton Inn Kimball$89

                      Hampton Inn Kimball$89

                      Top Flight Deals

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