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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.

Top Hotel Deals

See all 12 Hotels in Windsor
Quality Inn & Suites

Quality Inn & Suites

4922 Paradise Rd, Mattoon
    2.5 out of 5.0
     
     

    Located in the heart of Mattoon, this hotel is within 6 mi (10 km) of Kinzel Field, Mattoon City Hall, and Mattoon Peterson Park. Veteran's Monument and Kelly ...

    Quality Inn & Suites$109

    Quality Inn & Suites$109
    Super 8 by Wyndham Mattoon

    Super 8 by Wyndham Mattoon

    205 Mcfall Rd, Mattoon
      2.0 out of 5.0
       
       

      Situated in Mattoon, this hotel is 1.8 mi (2.9 km) from Mattoon Peterson Park and 2.9 mi (4.7 km) from Mattoon City Hall. Kinzel Field is 4.1 mi (6.6 km) ...

      Super 8 by Wyndham Mattoon$76

      Super 8 by Wyndham Mattoon$76
      Baymont by Wyndham Mattoon

      Baymont by Wyndham Mattoon

      206 Mcfall Rd, Mattoon
        2.5 out of 5.0
         
         

        Situated in Mattoon, this hotel is 1.8 mi (2.9 km) from Mattoon Peterson Park and 2.9 mi (4.7 km) from Mattoon City Hall. Kinzel Field is 4.1 mi (6.6 km) ...

        Baymont by Wyndham Mattoon$89

        Baymont by Wyndham Mattoon$89
        Comfort Suites Mattoon

        Comfort Suites Mattoon

        1408 Broadway Ave E, Mattoon
          2.5 out of 5.0
           
           

          Situated in Mattoon, this hotel is 1.8 mi (2.8 km) from Mattoon Peterson Park and 2.9 mi (4.6 km) from Mattoon City Hall. Kinzel Field is 3.9 mi (6.2 km) ...

          Comfort Suites Mattoon$110

          Comfort Suites Mattoon$110
          Holiday Inn Express & Suites Mattoon

          Holiday Inn Express & Suites Mattoon

          121 Swords Dr, Mattoon
            2.5 out of 5.0
             
             

            Situated in Mattoon, this hotel is 1.6 mi (2.6 km) from Mattoon Peterson Park and 2.7 mi (4.4 km) from Mattoon City Hall. Kinzel Field is 3.7 mi (6 km) ...

            Holiday Inn Express & Suites Mattoon$122

            Holiday Inn Express & Suites Mattoon$122
            Motel 6 Mattoon IL

            Motel 6 Mattoon IL

            4200 Lake Land Boulevard, Mattoon
              2.0 out of 5.0
               
               

              Situated in Mattoon, this motel is within 6 mi (10 km) of Mattoon City Hall, Kinzel Field, and Mattoon Peterson Park. Rockome Gardens and Veteran's Monument ...

              Motel 6 Mattoon IL$56

              Motel 6 Mattoon IL$56
              Suite Dreams Hotel

              Suite Dreams Hotel

              300 Broadway Avenue East, Mattoon
                2.5 out of 5.0
                 
                 

                Situated in Mattoon, this hotel is 0.7 mi (1.1 km) from Mattoon Peterson Park and within 3 mi (5 km) of Mattoon City Hall and Kinzel Field. Kelly Moore Memorial ...

                Suite Dreams Hotel$100

                Suite Dreams Hotel$100
                Hampton Inn Mattoon

                Hampton Inn Mattoon

                1416 Broadway Avenue East, Mattoon
                  2.5 out of 5.0
                   
                   

                  Situated in the business district, this hotel is 1.8 mi (3 km) from Mattoon Peterson Park and 2.9 mi (4.7 km) from Mattoon City Hall. Kinzel Field is 3.9 mi ...

                  Hampton Inn Mattoon$109

                  Hampton Inn Mattoon$109
                  Spillway Motel

                  Spillway Motel

                  1295 County Highway 6, Shelbyville
                    2.0 out of 5.0
                     
                     

                    Situated in Shelbyville, this motel is within 2 mi (3 km) of Shelby County Courthouse, Lake Shelbyville Beach, and Forest Park. Kinzel Field and Mattoon City ...

                    The Shelby Inn

                    The Shelby Inn

                    816 W Main Street, Shelbyville
                      2.5 out of 5.0
                       
                       

                      Situated in the historical district, this motel is 0.6 mi (1 km) from Shelby County Courthouse and within 3 mi (5 km) of Forest Park and Lake Shelbyville Beach. ...

                      Top Flight Deals

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