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

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 56 Properties in Windsor
Quail Hollow Resort Trademark Collection by Wyndham

Quail Hollow Resort Trademark Collection by Wyndham

11080 Concord-Hambden Rd, Painesville
    3.5 out of 5.0
     
     

    Situated in Painesville, this golf hotel is 2.7 mi (4.3 km) from Little Mountain Country Club and within 6 mi (10 km) of Lake Erie College and Lake County History ...

    Quail Hollow Resort Trademark Collection by Wyndham$71

    Quail Hollow Resort Trademark Collection by Wyndham$71
    Red Roof Inn Cleveland East - Willoughby

    Red Roof Inn Cleveland East - Willoughby

    4166 State Route 306, Willoughby
      2.0 out of 5.0
       
       

      Located in the heart of Willoughby, this hotel is within 6 mi (10 km) of Classic Park, Lake Metroparks Farmpark, and Mentor Civic Arena. Mentor Lagoons Nature ...

      Red Roof Inn Cleveland East - Willoughby$61

      Red Roof Inn Cleveland East - Willoughby$61
      Punderson Manor Lodge and Conference Center

      Punderson Manor Lodge and Conference Center

      11755 Kinsman Rd, Newbury
        3.5 out of 5.0
         
         

        Situated on the waterfront, this historic hotel is 0.3 mi (0.5 km) from Punderson State Park and 7.5 mi (12 km) from Alpine Valley. Aurora Farms Premium Outlets ...

        Punderson Manor Lodge and Conference Center$144

        Punderson Manor Lodge and Conference Center$144
        Americas Best Value Inn Austinburg

        Americas Best Value Inn Austinburg

        2352 State Route 45 N, Austinburg
          2.0 out of 5.0
           
           

          Located in the heart of Austinburg, this motel is within 1 mi (2 km) of Austinburg Township Park and Maple Ridge Golf Course. Harpersfield Covered Bridge and ...

          Americas Best Value Inn Austinburg$59

          Americas Best Value Inn Austinburg$59
          Best Western Plus Lawnfield Inn & Suites

          Best Western Plus Lawnfield Inn & Suites

          8434 Mentor Avenue, Mentor
            3.0 out of 5.0
             
             

            Situated in Mentor, this hotel is 0.6 mi (1 km) from James Garfield National Historic Site and 2.6 mi (4.2 km) from Mentor Civic Arena. Mentor Lagoons Nature ...

            Best Western Plus Lawnfield Inn & Suites$109

            Best Western Plus Lawnfield Inn & Suites$109
            Hampton Inn Ashtabula

            Hampton Inn Ashtabula

            2900 GH Dr, Austinburg
              2.5 out of 5.0
               
               

              Situated in Austinburg, this hotel is 0.8 mi (1.3 km) from Austinburg Township Park and 1.5 mi (2.3 km) from Maple Ridge Golf Course. Harpersfield Covered Bridge ...

              Hampton Inn Ashtabula$125

              Hampton Inn Ashtabula$125
              Ramada by Wyndham Austinburg/Ashtabula

              Ramada by Wyndham Austinburg/Ashtabula

              1860 Austinburg-Ashtabula Rd, Austinburg
                3.0 out of 5.0
                 
                 

                Located in the heart of Austinburg, this historic hotel is within 1 mi (2 km) of Maple Ridge Golf Course and Austinburg Township Park. Mechanicsville Road Covered ...

                Ramada by Wyndham Austinburg/Ashtabula$83

                Ramada by Wyndham Austinburg/Ashtabula$83
                Motel 6 Geneva OH

                Motel 6 Geneva OH

                1715 S Broadway, Geneva
                  2.0 out of 5.0
                   
                   

                  Situated in Geneva, this motel is within 1 mi (2 km) of Ferrante Winery and Harpersfield Covered Bridge. Laurello Vineyards and The Winery at Spring Hill are ...

                  Motel 6 Geneva OH$76

                  Motel 6 Geneva OH$76
                  Sleep Inn & Suites Near I-90 and Ashtabula

                  Sleep Inn & Suites Near I-90 and Ashtabula

                  9350 Center Rd, Austinburg
                    2.5 out of 5.0
                     
                     

                    Located in the heart of Austinburg, this hotel is 1 mi (1.6 km) from Maple Ridge Golf Course and 1.3 mi (2 km) from Austinburg Township Park. Mechanicsville ...

                    Sleep Inn & Suites Near I-90 and Ashtabula$109

                    Sleep Inn & Suites Near I-90 and Ashtabula$109
                    Hampton Inn & Suites Cleveland Mentor

                    Hampton Inn & Suites Cleveland Mentor

                    5675 Emerald Ct, Mentor
                      2.5 out of 5.0
                       
                       

                      Situated in Mentor, this hotel is 2.9 mi (4.6 km) from Mentor Civic Arena and 3.1 mi (5 km) from Lake Erie College. Mentor Marsh - Carol H. Sweet Nature Center ...

                      Hampton Inn & Suites Cleveland Mentor$115

                      Hampton Inn & Suites Cleveland Mentor$115

                      Top Flight Deals

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