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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 131 Properties in Windsor
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

1032 South Street, Pittsfield
    3.0 out of 5.0
     
     

    Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

    Hilton Garden Inn Lenox Pittsfield$127

    Hilton Garden Inn Lenox Pittsfield$127
    Yankee Inn

    Yankee Inn

    461 Pittsfield Rd, Lenox
      2.5 out of 5.0
       
       

      Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

      Yankee Inn$93

      Yankee Inn$93
      The Orchards Hotel

      The Orchards Hotel

      222 Adams Rd, Williamstown
        3.5 out of 5.0
         
         

        Situated in a rural location, this hotel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and Chapin Library of Rare Books and Manuscripts. ...

        The Orchards Hotel$179

        The Orchards Hotel$179
        Berkshire Hills Country Inn

        Berkshire Hills Country Inn

        1146 Cold Spring Road, Williamstown
          2.5 out of 5.0
           
           

          Situated in Williamstown, this hotel is within 3 mi (5 km) of Williamstown Historical Museum, Waubeeka Golf Links, and 62 Center for Theater and Dance. Chapin ...

          Berkshire Hills Country Inn$80

          Berkshire Hills Country Inn$80
          Hampton Inn & Suites Berkshires Lenox

          Hampton Inn & Suites Berkshires Lenox

          445 Pittsfield Rd, Lenox
            2.5 out of 5.0
             
             

            Situated in a rural location, this hotel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary ...

            Hampton Inn & Suites Berkshires Lenox$118

            Hampton Inn & Suites Berkshires Lenox$118
            Vacation Village in the Berkshires

            Vacation Village in the Berkshires

            276 Brodie Mountain Rd, Hancock
              3.0 out of 5.0
               
               

              Situated in Hancock, this condo building is within 9 mi (15 km) of Mount Greylock State Reservation Visitor Center, Pittsfield State Forest, and Waubeeka Golf ...

              Vacation Village in the Berkshires$135

              Vacation Village in the Berkshires$135
              Courtyard by Marriott Lenox Berkshires

              Courtyard by Marriott Lenox Berkshires

              70 Pittsfield Rd, Lenox
                3.0 out of 5.0
                 
                 

                Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded ...

                Courtyard by Marriott Lenox Berkshires$152

                Courtyard by Marriott Lenox Berkshires$152
                Cranwell Spa and Golf Resort

                Cranwell Spa and Golf Resort

                55 Lee Road, Lenox
                  3.5 out of 5.0
                   
                   

                  Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company ...

                  Cranwell Spa and Golf Resort$159

                  Cranwell Spa and Golf Resort$159
                  Berkshire Mountain Lodge

                  Berkshire Mountain Lodge

                  8 Dan Fox Dr, Pittsfield
                    3.0 out of 5.0
                     
                     

                    Situated in Pittsfield, this lodge is 1 mi (1.7 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

                    Berkshire Mountain Lodge$122

                    Berkshire Mountain Lodge$122
                    The Williams Inn

                    The Williams Inn

                    1090 Main Street, Williamstown
                      3.0 out of 5.0
                       
                       

                      Situated in Williamstown, this hotel is within a 5-minute walk of Williamstown Historical Museum and 62 Center for Theater and Dance. Chapin Library of Rare ...

                      The Williams Inn$145

                      The Williams Inn$145

                      Top Flight Deals

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