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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 210 Hotels in Winchester
La Quinta Inn & Suites Winchester

La Quinta Inn & Suites Winchester

1055 Millwood Pike, Route 50 East, Winchester
    3.0 out of 5.0
     
     

    Situated in the suburbs, this hotel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

    La Quinta Inn & Suites Winchester$98

    La Quinta Inn & Suites Winchester$98
    Country Inn & Suites by Radisson, Winchester, VA

    Country Inn & Suites by Radisson, Winchester, VA

    141 Kernstown Commons Blvd, Winchester
      3.0 out of 5.0
       
       

      Situated in Winchester, this hotel is within 6 mi (10 km) of The Kernstown Battlefield, Shenandoah University, and Rock Harbor Golf Course. Shenandoah Valley ...

      Country Inn & Suites by Radisson, Winchester, VA$71

      Country Inn & Suites by Radisson, Winchester, VA$71
      Travelodge by Wyndham Winchester

      Travelodge by Wyndham Winchester

      160 Front Royal Pike, Winchester
        2.0 out of 5.0
         
         

        Situated in Winchester, this motel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

        Travelodge by Wyndham Winchester$57

        Travelodge by Wyndham Winchester$57
        Comfort Inn Winchester

        Comfort Inn Winchester

        1601 Martinsburg Pike, Winchester
          2.5 out of 5.0
           
           

          Set in Winchester, this family-friendly hotel is within 6 mi (10 km) of Stonewall Jackson's Headquarters, Apple Blossom Mall, and Jim Barnett Park. Bright Box ...

          Comfort Inn Winchester$99

          Comfort Inn Winchester$99
          Wingate by Wyndham Winchester

          Wingate by Wyndham Winchester

          150 Wingate Dr, Winchester
            2.5 out of 5.0
             
             

            Situated in Winchester, this hotel is within a 10-minute walk of Abram's Delight, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

            Wingate by Wyndham Winchester$93

            Wingate by Wyndham Winchester$93
            Red Roof Inn Winchester, VA

            Red Roof Inn Winchester, VA

            991 Millwood Pike, Winchester
              2.0 out of 5.0
               
               

              Located in the heart of Winchester, this hotel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and ...

              Red Roof Inn Winchester, VA$65

              Red Roof Inn Winchester, VA$65
              Motel 6 Winchester, VA

              Motel 6 Winchester, VA

              2951 Valley Avenue, Winchester
                2.0 out of 5.0
                 
                 

                Located in the heart of Winchester, this motel is 0.6 mi (1 km) from The Kernstown Battlefield and within 3 mi (5 km) of Apple Blossom Mall and Abram's Delight. ...

                Motel 6 Winchester, VA$57

                Motel 6 Winchester, VA$57
                Holiday Inn Winchester Se-Historic Gateway

                Holiday Inn Winchester Se-Historic Gateway

                333 Front Royal Pike, Winchester
                  3.0 out of 5.0
                   
                   

                  Situated near the airport, this hotel is 1.1 mi (1.7 km) from Shenandoah University and within 3 mi (5 km) of Apple Blossom Mall and Jim Barnett Park. George ...

                  Holiday Inn Winchester Se-Historic Gateway$97

                  Holiday Inn Winchester Se-Historic Gateway$97
                  Wayside Inn

                  Wayside Inn

                  7783 Main St, Middletown
                    3.5 out of 5.0
                     
                     

                    Situated in Middletown, this inn is within 1 mi (2 km) of Wayside Theater and Cedar Creek and Belle Grove National Historical Park. Cedar Creek Battlefield Foundation ...

                    Wayside Inn$95

                    Wayside Inn$95
                    Super 8 by Wyndham Front Royal

                    Super 8 by Wyndham Front Royal

                    111 South St, Front Royal
                      2.0 out of 5.0
                       
                       

                      Located in Front Royal Entrance Shenandoah National Park, this hotel is within a 10-minute walk of Blue Ridge Arts Council and Gallery and Front Royal Visitor's ...

                      Super 8 by Wyndham Front Royal$54

                      Super 8 by Wyndham Front Royal$54

                      Top Flight Deals

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