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See all 162 Properties in Windsor
Berkshire Plaza Hotel

Berkshire Plaza Hotel

1 West St, Pittsfield
    3.5 out of 5.0
     
     

    Located in the heart of Pittsfield, this spa hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

    Berkshire Plaza Hotel$91

    Berkshire Plaza Hotel$91
    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
      Jiminy Peak Mountain Resort

      Jiminy Peak Mountain Resort

      37 Corey Rd, Hancock
        3.0 out of 5.0
         
         

        Located in the mountains, this Hancock condo resort offers ski-in/ski-out access within 12 mi (20 km) of Mount Greylock State Reservation Visitor Center, Waubeeka ...

        Jiminy Peak Mountain Resort$129

        Jiminy Peak Mountain Resort$129
        Black Swan Inn, an Ascend Collection Hotel

        Black Swan Inn, an Ascend Collection Hotel

        435 Laurel St, Lee
          3.0 out of 5.0
           
           

          Situated on a lake, this hotel is within 1 mi (2 km) of Animagic Museum of Animation and Lee Library. Greenock Country Club and The Mount are also within 3 mi ...

          Black Swan Inn, an Ascend Collection Hotel$110

          Black Swan Inn, an Ascend Collection Hotel$110
          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$99

            Berkshire Hills Country Inn$99
            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$150

              The Williams Inn$150
              Berkshire Inn

              Berkshire Inn

              150 W Housatonic St, Pittsfield
                2.0 out of 5.0
                 
                 

                Located in the heart of Pittsfield, this motel is within a 15-minute walk of Colonial Theater and Berkshire Museum. Berkshire Athenaeum and Canoe Meadows Wildlife ...

                Berkshire Inn$75

                Berkshire Inn$75
                Seven Hills Inn

                Seven Hills Inn

                40 Plunkett Street, Lenox
                  4.0 out of 5.0
                   
                   

                  This family-friendly Lenox inn is within 2 mi (3 km) of The Mount, Shakespeare and Company, and Ventfort Hall Mansion and Gilded Age Museum. Lenox Library and ...

                  Seven Hills Inn$149

                  Seven Hills Inn$149
                  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$76

                    Yankee Inn$76
                    Super 8 by Wyndham Lee/Berkshires/Outlet Area

                    Super 8 by Wyndham Lee/Berkshires/Outlet Area

                    170 Housatonic Street, Lee
                      2.0 out of 5.0
                       
                       

                      Situated in Lee, this motel is within a 15-minute walk of Lee Prime Outlets, Lee Library, and Animagic Museum of Animation. Greenock Country Club and Beartown ...

                      Super 8 by Wyndham Lee/Berkshires/Outlet Area$76

                      Super 8 by Wyndham Lee/Berkshires/Outlet Area$76

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