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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 621 Properties in Windsor
Snapdragon Inn

Snapdragon Inn

26 Main Street, Windsor
    3.5 out of 5.0
     
     

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

    Snapdragon Inn$224

    Snapdragon Inn$224
    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 ...

      Windsor Mansion Inn$179

      Windsor Mansion Inn$179
      West Windsor Retreat Vacation Home 3

      West Windsor Retreat Vacation Home 3

      607 Bannister Rd, Windsor
        3.5 out of 5.0
         
         

        Situated in Windsor, this vacation home is 4.2 mi (6.7 km) from Mt Ascutney State Park and within 12 mi (20 km) of American Precision Museum and South Congregational ...

        Killington Mountain Lodge, BW Signature Collection

        Killington Mountain Lodge, BW Signature Collection

        2617 Killington Rd, Killington
          3.5 out of 5.0
           
           

          Conveniently near skiing facilities, this Killington hotel is located in the mountains, within 3 mi (5 km) of Killington Golf Course and Killington Resort, and ...

          Killington Mountain Lodge, BW Signature Collection$89

          Killington Mountain Lodge, BW Signature Collection$89
          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
            Fireside Inn & Suites West Lebanon

            Fireside Inn & Suites West Lebanon

            25 Airport Road, West Lebanon
              2.5 out of 5.0
               
               

              Situated in West Lebanon, this hotel is within 3 mi (5 km) of Main Street Museum, Briggs Opera House, and New England Transportation Institute and Museum. Tupelo ...

              Fireside Inn & Suites West Lebanon$121

              Fireside Inn & Suites West Lebanon$121
              The Shire Woodstock

              The Shire Woodstock

              46 Pleasant St., Woodstock
                3.0 out of 5.0
                 
                 

                Situated in Woodstock, this hotel is within a 15-minute walk of Dana House Museum, Billings Park and Trail, and Woodstock Town Hall Theatre. Mount Tom Peak and ...

                The Shire Woodstock$149

                The Shire Woodstock$149
                Baymont by Wyndham West Lebanon

                Baymont by Wyndham West Lebanon

                45 Airport Road, West Lebanon
                  2.0 out of 5.0
                   
                   

                  Situated near the airport, this hotel is within 3 mi (5 km) of Main Street Museum, Briggs Opera House, and New England Transportation Institute and Museum. Tupelo ...

                  Baymont by Wyndham West Lebanon$94

                  Baymont by Wyndham West Lebanon$94
                  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 ...

                    Chalet Killington$85

                    Chalet Killington$85
                    Element Hanover Lebanon

                    Element Hanover Lebanon

                    25 Foothill Street, Lebanon
                      3.0 out of 5.0
                       
                       

                      Situated in Lebanon, this hotel is within 3 mi (5 km) of Dartmouth-Hitchcock Medical Center, Lebanon Opera House, and AVA Gallery and Art Center. Thompson Arena ...

                      Element Hanover Lebanon$149

                      Element Hanover Lebanon$149

                      Top Flight Deals

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