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Upperville Vacations

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

Hotwire can help you find your travel bliss with Upperville 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 Upperville

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 Upperville 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 Upperville well.

Top Hotel Deals

See all 81 Properties in Upperville
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
    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$89

      La Quinta Inn & Suites Winchester$89
      Comfort Inn Winchester

      Comfort Inn Winchester

      1601 Martinsburg Pike, Winchester
        2.5 out of 5.0
         
         

        Situated in Winchester, this hotel is within 6 mi (10 km) of Stonewall Jackson's Headquarters, Handley Regional Library, and Mt Hebron Cemetery. Bright Box Theater ...

        Comfort Inn Winchester$79

        Comfort Inn Winchester$79
        Super 8 by Wyndham Winchester VA

        Super 8 by Wyndham Winchester VA

        1077 Millwood Pike, Winchester
          2.0 out of 5.0
           
           

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

          Super 8 by Wyndham Winchester VA$51

          Super 8 by Wyndham Winchester VA$51
          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
            Hampton Inn Front Royal

            Hampton Inn Front Royal

            9800 Winchester Rd, Front Royal
              2.5 out of 5.0
               
               

              Situated in the mountains, this hotel is within 3 mi (5 km) of Blue Ridge Shadows Golf Club, Bing Crosby Stadium, and Belle Boyd Cottage. Warren Rifles Confederate ...

              Hampton Inn Front Royal$112

              Hampton Inn Front Royal$112
              Airlie

              Airlie

              6809 Airlie Road, Warrenton
                3.5 out of 5.0
                 
                 

                Situated in a rural location, this historic hotel is within 6 mi (10 km) of Old Jail Museum, Liberty Heritage Society Museum, and Marterella Winery. Mediterranean ...

                Airlie$190

                Airlie$190
                SpringHill Suites by Marriott Gainesville Haymarket

                SpringHill Suites by Marriott Gainesville Haymarket

                7921 Gateway Promenade Place, Gainesville
                  2.5 out of 5.0
                   
                   

                  Situated in Gainesville, this hotel is 1.7 mi (2.7 km) from Jiffy Lube Live and within 6 mi (10 km) of Manassas National Battlefield Park and Vint Hill Craft ...

                  SpringHill Suites by Marriott Gainesville Haymarket$158

                  SpringHill Suites by Marriott Gainesville Haymarket$158
                  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$55

                    Travelodge by Wyndham Winchester$55
                    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 and Winchester-Frederick County Convention & Visitors Bureau. Apple Blossom ...

                      Wingate by Wyndham Winchester$93

                      Wingate by Wyndham Winchester$93

                      Top Flight Deals

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