Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Top Hotel Deals

See all 443 Properties in Pittsfield
Clear River Inn

Clear River Inn

2640 Route 100, Pittsfield
    3.0 out of 5.0
     
     

    Situated in Pittsfield, this inn is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and Pico Mountain at Killington Ski ...

    Casa Bella Inn & Restaurant

    Casa Bella Inn & Restaurant

    3911 Route 100 North, Pittsfield
      3.0 out of 5.0
       
       

      Situated in the mountains, this inn is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and White River Golf Club. Pico ...

      Casa Bella Inn & Restaurant$115

      Casa Bella Inn & Restaurant$115
      Hawk Landing by RedAwning

      Hawk Landing by RedAwning

      132 Hawk Ln, Pittsfield
        3.5 out of 5.0
         
         

        Situated in Pittsfield, this vacation home is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and White River Golf Club. ...

        Sweet Life

        Sweet Life

        64 Dove Drive, Pittsfield
          3.5 out of 5.0
           
           

          Situated in Pittsfield, this vacation home is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and White River Golf Club. ...

          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$99

            Killington Mountain Lodge, BW Signature Collection$99
            Days Inn by Wyndham Rutland/Killington Area

            Days Inn by Wyndham Rutland/Killington Area

            401 Us Route 7 S, Rutland
              2.5 out of 5.0
               
               

              Situated in Rutland, this hotel is 0.9 mi (1.4 km) from Rutland Country Club and within 3 mi (5 km) of Hathaway Farm and Pine Hill Park. Paramount Theater and ...

              Days Inn by Wyndham Rutland/Killington Area$64

              Days Inn by Wyndham Rutland/Killington Area$64
              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
                Middlebury Inn

                Middlebury Inn

                14 Court Square, Middlebury
                  3.0 out of 5.0
                   
                   

                  Located in the heart of Middlebury, this spa hotel is within a 15-minute walk of Town Hall Theater and Middlebury College. National Museum of the Morgan Horse ...

                  Middlebury Inn$135

                  Middlebury Inn$135
                  Woodstock Inn & Resort

                  Woodstock Inn & Resort

                  Fourteen The Green, Woodstock
                    3.5 out of 5.0
                     
                     

                    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$399

                    Woodstock Inn & Resort$399
                    506 On the River Inn

                    506 On the River Inn

                    1653 West Woodstock Road, Woodstock
                      4.0 out of 5.0
                       
                       

                      This family-friendly Woodstock hotel is located in the historical district, within 2 mi (3 km) of Union Arena Community Center, Marsh-Billings-Rockefeller National ...

                      506 On the River Inn$300

                      506 On the River Inn$300

                      Top Flight Deals

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