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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 164 Hotels in Winchester
Red Roof Inn Lexington - Winchester

Red Roof Inn Lexington - Winchester

1100 Interstate Drive, Winchester
    2.0 out of 5.0
     
     

    Situated in Winchester, this motel is 1.2 mi (1.9 km) from Lykins Park and within 3 mi (5 km) of Bluegrass Heritage Museum and Community Park. Clark Regional ...

    Red Roof Inn Lexington - Winchester$54

    Red Roof Inn Lexington - Winchester$54
    Baymont by Wyndham Winchester

    Baymont by Wyndham Winchester

    960 Interstate Dr, Winchester
      2.5 out of 5.0
       
       

      Situated in Winchester, this hotel is 1.2 mi (1.9 km) from Lykins Park and within 3 mi (5 km) of Bluegrass Heritage Museum and Community Park. Clark Regional ...

      Baymont by Wyndham Winchester$85

      Baymont by Wyndham Winchester$85
      Hampton Inn Winchester

      Hampton Inn Winchester

      1025 Early Dr, Winchester
        2.5 out of 5.0
         
         

        Located in the heart of Winchester, this hotel is within 2 mi (3 km) of Lykins Park, Bluegrass Heritage Museum, and Community Park. Clark Regional Medical Center ...

        Hampton Inn Winchester$143

        Hampton Inn Winchester$143
        Comfort Inn

        Comfort Inn

        5250 Revilo Rd, Winchester
          2.5 out of 5.0
           
           

          Located in the heart of Winchester, this hotel is within 3 mi (5 km) of Clark Regional Medical Center, Community Park, and Cassell Creek Golf Course. Bluegrass ...

          Comfort Inn$75

          Comfort Inn$75
          Holiday Inn Express Lexington East - Winchester

          Holiday Inn Express Lexington East - Winchester

          100 Winchester Plaza, Winchester
            2.5 out of 5.0
             
             
            GuestHouse Inn & Suites Lexington

            GuestHouse Inn & Suites Lexington

            2261 Elkhorn Road, Lexington
              2.5 out of 5.0
               
               

              Situated in a shopping district, this hotel is within 6 mi (10 km) of Castlewood Park, Mary Todd Lincoln House, and Rupp Arena. University of Kentucky and Commonwealth ...

              GuestHouse Inn & Suites Lexington$56

              GuestHouse Inn & Suites Lexington$56
              Microtel Inn by Wyndham Lexington

              Microtel Inn by Wyndham Lexington

              2240 Buena Vista Rd, Lexington
                2.0 out of 5.0
                 
                 

                Situated near the airport, this hotel is within 6 mi (10 km) of Castlewood Park, Mary Todd Lincoln House, and Rupp Arena. University of Kentucky and Commonwealth ...

                Microtel Inn by Wyndham Lexington$59

                Microtel Inn by Wyndham Lexington$59
                Ramada Hotel & Conference Center by Wyndham Lexington North

                Ramada Hotel & Conference Center by Wyndham Lexington North

                2143 N Broadway, Lexington
                  3.0 out of 5.0
                   
                   

                  Situated near the airport, this hotel is within 3 mi (5 km) of Whitaker Bank Ballpark, The Thoroughbred Center, and Castlewood Park. Loudoun House and West Sixth ...

                  Ramada Hotel & Conference Center by Wyndham Lexington North$61

                  Ramada Hotel & Conference Center by Wyndham Lexington North$61
                  Hyatt Place Lexington

                  Hyatt Place Lexington

                  2001 Bryant Rd, Lexington
                    3.0 out of 5.0
                     
                     

                    Located just off highway I-75, Hyatt Place Lexington is a 25-minute drive from Blue Grass Airport. Sights and attractions within a 20-minute drive include central ...

                    Hyatt Place Lexington$98

                    Hyatt Place Lexington$98
                    Red Roof Inn Lexington South

                    Red Roof Inn Lexington South

                    2651 Wilhite Dr, Lexington
                      2.0 out of 5.0
                       
                       

                      Situated in Lexington, this motel is 0.7 mi (1.1 km) from The Mall At Lexington Green and within 3 mi (5 km) of Commonwealth Stadium and University of Kentucky. ...

                      Red Roof Inn Lexington South$54

                      Red Roof Inn Lexington South$54

                      Top Flight Deals

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