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Windsor Vacations

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

Hotwire can help you find your travel bliss with Windsor 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 Windsor

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 Windsor 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 Windsor well.

Windsor Flight + Hotel packages

Top Hotel Deals

See all 3,126 Hotels in Windsor
De Vere Beaumont Estate

De Vere Beaumont Estate

Burfield Road, Berkshire, Windsor
    4.0 out of 5.0
     
     

    Situated in a rural location, this eco-friendly hotel is 3 mi (4.8 km) from Windsor Castle and within 6 mi (10 km) of Windsor Racecourse and Legoland. Thorpe ...

    Clarion Collection Harte & Garter Hotel & Spa

    Clarion Collection Harte & Garter Hotel & Spa

    31 High Street, Windsor
      4.0 out of 5.0
       
       

      Located in Windsor City Centre, this hotel is steps from Windsor Castle, Windsor Parish Church, and Windsor Guildhall. Windsor Royal Shopping Centre and Theatre ...

      Clarion Collection Harte & Garter Hotel & Spa$110

      Clarion Collection Harte & Garter Hotel & Spa$110
      Macdonald Windsor Hotel

      Macdonald Windsor Hotel

      23 High Street, Windsor
        4.0 out of 5.0
         
         

        Located in Windsor City Centre, this eco-friendly hotel is steps from Windsor Parish Church and Windsor Castle. Legoland and Eton College are also within 3 mi ...

        Macdonald Windsor Hotel$165

        Macdonald Windsor Hotel$165
        The Oakley Court

        The Oakley Court

        Windsor Road, Windsor
          4.0 out of 5.0
           
           

          A 5-minute drive from Royal Windsor Racecourse, The Oakley Court is set on a 33 acres of private land overlooking the River Thames, 10 minutes from Windsor Castle ...

          The Oakley Court$168

          The Oakley Court$168
          The Crown and Cushion

          The Crown and Cushion

          84 Hight Street, Windsor
            3.0 out of 5.0
             
             

            Situated in Eton, this guesthouse is within a 10-minute walk of Windsor Bridge, Windsor Castle, and Eton College. Legoland and Frogmore House are also within ...

            Castle Hotel Windsor MGallery Collection

            Castle Hotel Windsor MGallery Collection

            18 High Street, Windsor
              4.0 out of 5.0
               
               

              Located in Windsor City Centre, this hotel is steps from Windsor Parish Church and Windsor Castle. Legoland and Eton College are also within 3 mi (5 km).

              Castle Hotel Windsor MGallery Collection$116

              Castle Hotel Windsor MGallery Collection$116
              Sir Christopher Wren Hotel and Spa

              Sir Christopher Wren Hotel and Spa

              Thames Street, Windsor
                4.0 out of 5.0
                 
                 

                Located in Windsor City Centre, this spa hotel is within a 10-minute walk of Windsor Bridge, Windsor Castle, and Eton College. Legoland and Frogmore House are ...

                Sir Christopher Wren Hotel and Spa$152

                Sir Christopher Wren Hotel and Spa$152
                The Royal Adelaide Hotel

                The Royal Adelaide Hotel

                46 Kings Road, Windsor
                  3.5 out of 5.0
                   
                   

                  Situated in Windsor, this hotel is within a 15-minute walk of Windsor Guildhall and Windsor Castle. Eton College and Frogmore House are also within 2 mi (3 ...

                  Holiday Inn Express Windsor

                  Holiday Inn Express Windsor

                  71 Alma Road, Windsor
                    3.0 out of 5.0
                     
                     

                    Located in the heart of Windsor, this hotel is within a 15-minute walk of Windsor Parish Church and Windsor Castle. Eton College and Frogmore House are also ...

                    Holiday Inn Express Windsor$73

                    Holiday Inn Express Windsor$73
                    The Union Inn

                    The Union Inn

                    17 Crimp Hill Road, Windsor
                      4.0 out of 5.0
                       
                       

                      Situated in a rural location, this inn is within 3 mi (5 km) of Runnymede, Windsor Castle, and Frogmore House. Windsor Guildhall and Windsor Parish Church are ...

                      The Union Inn$81

                      The Union Inn$81

                      Top Flight Deals

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