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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 630 Hotels in Windsor
Windsor Mansion Inn

Windsor Mansion Inn

153 Pembroke Road, Windsor
    3.5 out of 5.0
     
     

    Situated in Windsor, this bed & breakfast is within 2 mi (3 km) of Old Constitution House, South Congregational Church, and American Precision Museum. Cornish-Windsor ...

    Snapdragon Inn

    Snapdragon Inn

    26 Main Street, Windsor
       
       

      Situated in Windsor, this bed & breakfast is within a 10-minute walk of Old Constitution House and South Congregational Church. American Precision Museum and ...

      West Windsor Retreat Vacation Home 3

      West Windsor Retreat Vacation Home 3

      607 Bannister Rd, Windsor
         
         

        Situated in West Windsor, this vacation home is in the same area as Mount Ascutney, Mt Ascutney State Park, and Path of Life Garden. Area attractions also include ...

        Hillside Inn at Killington

        Hillside Inn at Killington

        375 Killington Rd, Killington
          2.0 out of 5.0
           
           

          Conveniently near skiing facilities, this Killington motel is located in the mountains, within 3 mi (5 km) of Gifford Woods State Park and Pico Mountain at Killington ...

          Hillside Inn at Killington$65

          Hillside Inn at Killington$65
          Chalet Killington

          Chalet Killington

          2685 Killington Rd, Killington
            2.5 out of 5.0
             
             

            Conveniently near skiing facilities, this Killington hotel is within 3 mi (5 km) of Killington Golf Course and Killington Resort and close to winter sports such ...

            Pointe at Castle Hill Resort

            Pointe at Castle Hill Resort

            2940 State Route 103, Proctorsville
              3.5 out of 5.0
               
               

              Situated in a rural location, this spa hotel is within 6 mi (10 km) of Dorsey Park, Okemo Mountain Resort, and Okemo Valley Golf Club. Buttermilk Falls and Camp ...

              Pointe at Castle Hill Resort$169

              Pointe at Castle Hill Resort$169
              Hotel Coolidge

              Hotel Coolidge

              39 South Main Street, Hartford
                3.0 out of 5.0
                 
                 

                Located in the heart of Hartford, this hotel is steps from Briggs Opera House and New England Transportation Institute and Museum. Main Street Museum and Tupelo ...

                Hotel Coolidge$76

                Hotel Coolidge$76
                Woodstock Inn & Resort

                Woodstock Inn & Resort

                Fourteen The Green, Woodstock
                   
                   

                  Situated in Woodstock, this resort is within a 5-minute walk of Woodstock Town Hall Theatre and Dana House Museum. Billings Park and Trail and Mount Tom Peak ...

                  Woodstock Inn & Resort$125

                  Woodstock Inn & Resort$125
                  Mountain Green Ski & Golf Resort

                  Mountain Green Ski & Golf Resort

                  133 E Mountain Rd, Killington
                    3.0 out of 5.0
                     
                     

                    Situated in the mountains, this spa condo resort is within 1 mi (2 km) of Killington Golf Course and Killington Resort. Pico Mountain at Killington Ski Resort ...

                    Comfort Inn

                    Comfort Inn

                    56 Ralph Lehman Dr, Hartford
                      2.5 out of 5.0
                       
                       

                      Situated in Hartford, this hotel is within 2 mi (3 km) of Upper Valley Aquatic Center, Briggs Opera House, and Main Street Museum. Tupelo Music Hall and New ...

                      Comfort Inn$99

                      Comfort Inn$99

                      Top Flight Deals

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