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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 682 Properties in Winchester
The Winchester Hotel & Spa

The Winchester Hotel & Spa

Worthy Lane, Winchester
    4.0 out of 5.0
     
     

    Located in the heart of Winchester, this spa hotel is within a 15-minute walk of Theatre Royal Winchester, Great Hall, and Winchester Cathedral. Westgate Museum ...

    The Winchester Hotel & Spa$95

    The Winchester Hotel & Spa$95
    Days Inn Winchester M3

    Days Inn Winchester M3

    Moto Motorway Service Area, Winchester
      2.0 out of 5.0
       
       

      Situated in Winchester, this hotel is within 6 mi (10 km) of Winnall Moors Nature Reserve, Great Hall, and Winchester City Mill. Winchester Guildhall and Westgate ...

      Days Inn Winchester M3$42

      Days Inn Winchester M3$42
      Mercure Wessex Winchester Hotel

      Mercure Wessex Winchester Hotel

      Paternoster Row, Winchester
        4.0 out of 5.0
         
         

        Located in the heart of Winchester, this hotel is steps from Winchester Guildhall and Winchester Cathedral. Great Hall is 0.4 mi (0.7 km) away.

        Mercure Wessex Winchester Hotel$64

        Mercure Wessex Winchester Hotel$64
        Marwell Hotel

        Marwell Hotel

        Thompson Lane, Winchester
          3.0 out of 5.0
           
           

          Situated in a rural location, this hotel is 0.2 mi (0.2 km) from Marwell Zoo and within 9 mi (15 km) of University of Southampton and Winchester Cathedral. Great ...

          Marwell Hotel$95

          Marwell Hotel$95
          BW Premier Collection Winchester Royal Hotel

          BW Premier Collection Winchester Royal Hotel

          St Peter Street, Winchester
            4.0 out of 5.0
             
             

            Located in the heart of Winchester, this romantic hotel is within a 5-minute walk of Theatre Royal Winchester and Winchester Cathedral. Great Hall is 0.3 mi ...

            BW Premier Collection Winchester Royal Hotel$75

            BW Premier Collection Winchester Royal Hotel$75
            Lainston House Hotel

            Lainston House Hotel

            Woodman Lane, Winchester
              5.0 out of 5.0
               
               

              Situated in Winchester, this luxury hotel is within 3 mi (5 km) of Sparsholt College, Great Hall, and Winchester Cathedral. Westgate Museum and Gurkha Museum ...

              Lainston House Hotel$208

              Lainston House Hotel$208
              Norton Park

              Norton Park

              Sutton Scotney, Winchester
                4.0 out of 5.0
                 
                 

                Situated near the airport, this spa hotel is within 9 mi (15 km) of Whitchurch Silk Mill, Great Hall, and St Mary's Church. Gurkha Museum Winchester and Royal ...

                Norton Park$119

                Norton Park$119
                Holiday Inn Winchester

                Holiday Inn Winchester

                Telegraph Way Morn Hill, Winchester
                  4.0 out of 5.0
                   
                   

                  Situated in a rural location, this eco-friendly hotel is 0.1 mi (0.1 km) from Winchester Science Centre and Planetarium and within 3 mi (5 km) of Winchester ...

                  Holiday Inn Winchester$88

                  Holiday Inn Winchester$88
                  Hotel du Vin & Bistro Winchester

                  Hotel du Vin & Bistro Winchester

                  Southgate Street, Winchester
                    4.0 out of 5.0
                     
                     

                    Located in the heart of Winchester, this romantic hotel is steps from Queen Eleanors Garden and Great Hall. Winchester Cathedral is 0.2 mi (0.3 km) away.

                    Hotel du Vin & Bistro Winchester$136

                    Hotel du Vin & Bistro Winchester$136
                    The King Alfred Pub

                    The King Alfred Pub

                    11 Saxon Road, Winchester
                      4.0 out of 5.0
                       
                       

                      Situated in Winchester, this inn is within a 15-minute walk of Theatre Royal Winchester, Winchester Cathedral, and Great Hall. Winnall Moors Nature Reserve and ...

                      The King Alfred Pub$95

                      The King Alfred Pub$95