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 163 Hotels in Windsor
Hartford/Windsor Marriott Airport

Hartford/Windsor Marriott Airport

28 Day Hill Rd, Windsor
    3.5 out of 5.0
     
     

    Situated near the airport, this hotel is within 3 mi (5 km) of Windsor Arts Center, Windsor Historical Society, and Vintage Radio and Communications Museum of ...

    Hartford/Windsor Marriott Airport$95

    Hartford/Windsor Marriott Airport$95
    HYATT house Hartford North/Windsor

    HYATT house Hartford North/Windsor

    200 Corporate Dr, Windsor
      3.0 out of 5.0
       
       

      Situated near the airport, this hotel is 2.4 mi (3.9 km) from Windsor Arts Center and 2.5 mi (4 km) from Windsor Historical Society. Northwest Park and Keney ...

      HYATT house Hartford North/Windsor$104

      HYATT house Hartford North/Windsor$104
      Hilton Garden Inn Hartford North/Bradley Int'l Airport

      Hilton Garden Inn Hartford North/Bradley Int'l Airport

      555 Corporate Dr, Windsor
        3.0 out of 5.0
         
         

        Situated near the airport, this hotel is 2.4 mi (3.8 km) from Windsor Arts Center and 2.4 mi (3.9 km) from Windsor Historical Society. Northwest Park and Keney ...

        Hilton Garden Inn Hartford North/Bradley Int'l Airport$88

        Hilton Garden Inn Hartford North/Bradley Int'l Airport$88
        Courtyard by Marriott Hartford Windsor

        Courtyard by Marriott Hartford Windsor

        1 Day Hill Rd, Windsor
          3.0 out of 5.0
           
           

          This suburban hotel offers easy access to downtown Hartford (8 miles) and the airport (4 miles); nearby landmarks include the First Cathedral, the Basketball ...

          Courtyard by Marriott Hartford Windsor$79

          Courtyard by Marriott Hartford Windsor$79
          Residence Inn by Marriott Hartford/Windsor

          Residence Inn by Marriott Hartford/Windsor

          100 Dunfey Ln, Windsor
            3.0 out of 5.0
             
             

            Situated in Windsor, this aparthotel is 1.7 mi (2.7 km) from Windsor Arts Center and 2 mi (3.2 km) from Windsor Historical Society. Keney Park and Northwest ...

            Residence Inn by Marriott Hartford/Windsor$109

            Residence Inn by Marriott Hartford/Windsor$109
            Hampton Inn Hartford/Airport

            Hampton Inn Hartford/Airport

            2168 Poquonock Ave, Windsor
              2.5 out of 5.0
               
               

              Situated near the airport, this hotel is 2.9 mi (4.7 km) from Northwest Park and within 6 mi (10 km) of New England Air Museum and Oliver Ellsworth Homestead. ...

              Hampton Inn Hartford/Airport$101

              Hampton Inn Hartford/Airport$101
              The Goodwin Hotel

              The Goodwin Hotel

              1 Haynes St, Hartford
                3.5 out of 5.0
                 
                 

                Located in Downtown, this hotel is within a 10-minute walk of Theater Works and Bushnell Park. Mark Twain House and Trinity College are also within 3 mi (5 ...

                The Goodwin Hotel$159

                The Goodwin Hotel$159
                La Quinta Inn & Suites Springfield

                La Quinta Inn & Suites Springfield

                100 Congress Street, Springfield
                  3.0 out of 5.0
                   
                   

                  Located in the heart of Springfield, this hotel is within 1 mi (2 km) of Quadrangle and Springfield Armory. Naismith Memorial Basketball Hall of Fame is 1.4 ...

                  La Quinta Inn & Suites Springfield$98

                  La Quinta Inn & Suites Springfield$98
                  Travelodge by Wyndham Bradley Airport

                  Travelodge by Wyndham Bradley Airport

                  383 S Center St, Windsor Locks
                    3.0 out of 5.0
                     
                     

                    Situated near the airport, this hotel is 2 mi (3.3 km) from Oliver Ellsworth Homestead and within 6 mi (10 km) of Broad Brook Brewing and Connecticut Trolley ...

                    Travelodge by Wyndham Bradley Airport$50

                    Travelodge by Wyndham Bradley Airport$50
                    Clarion Hotel & Aqua Lagoon Waterpark

                    Clarion Hotel & Aqua Lagoon Waterpark

                    1080 Riverdale St, West Springfield
                      2.5 out of 5.0
                       
                       

                      This family-friendly hotel is located in the city center, within 3 mi (5 km) of Josiah Day House and Holyoke Mall. Springfield Armory and Naismith Memorial Basketball ...

                      Clarion Hotel & Aqua Lagoon Waterpark$99

                      Clarion Hotel & Aqua Lagoon Waterpark$99

                      Top Flight Deals

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