Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

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 7 Hotels in Winchester
Greenville Inn

Greenville Inn

851 Martin St, Greenville
    2.5 out of 5.0
     
     

    Located in the heart of Greenville, this hotel is 0.4 mi (0.6 km) from Caddie Shack Driving Range and 3 mi (4.9 km) from Turtle Creek Golf Course. The Winery ...

    Greenville Inn$86

    Greenville Inn$86
    Comfort Inn Greenville

    Comfort Inn Greenville

    1190 E Russ Rd, Greenville
      2.5 out of 5.0
       
       

      Located in the heart of Greenville, this hotel is 1.4 mi (2.2 km) from Caddie Shack Driving Range and within 9 mi (15 km) of Turtle Creek Golf Course and The ...

      Comfort Inn Greenville$94

      Comfort Inn Greenville$94
      Holiday Inn Express & Suites Portland

      Holiday Inn Express & Suites Portland

      100 Holiday Dr, Portland
        2.5 out of 5.0
         
         

        Situated in a rural location, this hotel is within 20 mi (32 km) of Lehman Park, Berne Clock Tower, and Berne Public Library. Randolph County Courthouse and ...

        Holiday Inn Express & Suites Portland$132

        Holiday Inn Express & Suites Portland$132
        Portland Inn

        Portland Inn

        1147 N US Highway 27, Portland
          2.0 out of 5.0
           
           

          Located in the heart of Portland, this hotel is within 16 mi (25 km) of Lehman Park, Berne Clock Tower, and Berne Public Library. Randolph County Courthouse ...

          Portland Inn$75

          Portland Inn$75
          Towne House Motel

          Towne House Motel

          209 E. Main St., Greenville
            2.0 out of 5.0
             
             

            Situated in Greenville, this motel is close to Caddie Shack Driving Range. Area attractions also include Turtle Creek Golf Course.

            Holiday Inn Express Hotel & Suites Greenville

            Holiday Inn Express Hotel & Suites Greenville

            1195 Russ Rd, Greenville
              2.5 out of 5.0
               
               

              Situated in a rural location, this hotel is 1.4 mi (2.2 km) from Caddie Shack Driving Range and within 9 mi (15 km) of Turtle Creek Golf Course and The Winery ...

              Holiday Inn Express Hotel & Suites Greenville$124

              Holiday Inn Express Hotel & Suites Greenville$124