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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • Sleeps 8
    Chalet #4335951
    1
      Exceptional! 5.0/5
      (6 reviews)
      avg/night
      • 4 BR
      • 3 BA
      • Sleeps 10
      House #129127vb
      6
        • 5 BR
        • 3 BA
        • Sleeps 14
        House #345355
        10
          Wonderful! 4.8/5
          (9 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 8
          Chalet #3642810
          9
            • 3 BR
            • 2 BA
            • Sleeps 10
            House #340808
            23
              Excellent! 4.6/5
              (10 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Sleeps 12
              House #334430
              10
                • 2 BR
                • 1 BA
                • Sleeps 8
                House #868730vb
                1
                  Wonderful! 4.8/5
                  (11 reviews)
                  avg/night
                  • 5 BR
                  • 2 BA
                  • Sleeps 12
                  House #622687vb
                  11
                    • 3 BR
                    • 2 BA
                    • Sleeps 20
                    Chalet #640519vb
                    2
                      • 4 BR
                      • 2 BA
                      • Sleeps 11
                      House #759492vb
                      0
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 15
                        House #148104vb
                        57
                          Wonderful! 4.8/5
                          (21 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 10
                          House #166942vb
                          21
                            Wonderful! 4.9/5
                            (9 reviews)
                            avg/night
                            • 3 BR
                            • 1 BA
                            • 1 HF BA
                            • Sleeps 8
                            House #429854vb
                            9
                              • 4 BR
                              • 2 BA
                              • Sleeps 8
                              House #3861821
                              0
                                • 5 BR
                                • 3 BA
                                • Sleeps 16
                                Condo #938633
                                1
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  House #764994vb
                                  0
                                    • 3 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 6
                                    House #4328487
                                    0
                                      Exceptional! 5.0/5
                                      (10 reviews)
                                      avg/night
                                      • 5 BR
                                      • 3 BA
                                      • Sleeps 14
                                      House #259766vb
                                      10
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        House #151465vb
                                        48
                                          Wonderful! 4.8/5
                                          (36 reviews)
                                          avg/night
                                          • 5 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 13
                                          House #119086
                                          36
                                            Exceptional! 5.0/5
                                            (5 reviews)
                                            avg/night
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Cabin #312902vb
                                            5
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 8
                                              Chalet #204550vb
                                              1
                                                • 6 BR
                                                • 3 BA
                                                • Sleeps 21
                                                House #935042vb
                                                3
                                                  Wonderful! 4.8/5
                                                  (19 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Farmhouse #394111vb
                                                  19
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    House #263559
                                                    22
                                                      Wonderful! 4.9/5
                                                      (10 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                      House #474848vb
                                                      10
                                                        Excellent! 4.7/5
                                                        (20 reviews)
                                                        avg/night
                                                        • 5 BR
                                                        • 2 BA
                                                        • Sleeps 22
                                                        House #94002vb
                                                        20
                                                          • 5 BR
                                                          • 3 BA
                                                          • 1 HF BA
                                                          • Sleeps 13
                                                          House #853465vb
                                                          7
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 5
                                                            Chalet #645213vb
                                                            8
                                                              • 3 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 10
                                                              House #3837975
                                                              1
                                                                Exceptional! 5.0/5
                                                                (7 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 3 BA
                                                                • Sleeps 6
                                                                House #772545vb
                                                                7
                                                                  • 6 BR
                                                                  • 3 BA
                                                                  • Sleeps 32
                                                                  House #76323vb
                                                                  37
                                                                    • 5 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 10
                                                                    House #868713vb
                                                                    2
                                                                      Exceptional! 5.0/5
                                                                      (10 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 13
                                                                      House #644647vb
                                                                      10
                                                                        Exceptional! 5.0/5
                                                                        (55 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        House #217614vb
                                                                        55
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 12
                                                                          Chalet #788299vb
                                                                          13
                                                                            Wonderful! 4.8/5
                                                                            (37 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            Condo #128197
                                                                            37
                                                                              Excellent! 4.4/5
                                                                              (5 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 6
                                                                              Condo #4081070
                                                                              5
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Condo #973368vb
                                                                                1
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • 2 HF BA
                                                                                  • Sleeps 12
                                                                                  House #4216957
                                                                                  2
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 8
                                                                                    House #264368
                                                                                    13
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      House #3861978
                                                                                      3
                                                                                        Wonderful! 4.9/5
                                                                                        (18 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        House #10877vb
                                                                                        18
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 10
                                                                                          Cabin #4018112
                                                                                          3
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Condo #3639177
                                                                                            0
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              House #126984
                                                                                              11
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 10
                                                                                                House #959109
                                                                                                0
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 18
                                                                                                  House #4328491
                                                                                                  0
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 8
                                                                                                    Townhome #4319000
                                                                                                    0
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 11
                                                                                                      House #918418vb
                                                                                                      2
                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield: Houses, Condos & More (300+)

                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      wonderful holiday escape

                                                                                                      5 of 5
                                                                                                      One of the best rental house we ever stayed. We read a previous negative review complaining about the heater setting and towel use, and was a bit worried. But that turned out to be over exaggerated. Everything is in good shape (well, the heater controller is a bit dated, but I think anyone with minimal experience can easily handle that). The owner even provides the ski trail map and hand and toe warmer for us.
                                                                                                      • Submitted: Jan 8, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Wonderful rental for skiing and snowmobiling!!

                                                                                                      5 of 5
                                                                                                      We had a terrific stay over the New Years holiday here. Place was clean and comfortable. Excellent communication with the owners. We skied both killington 15 mins and sugarbush 45 mins. The property has beautiful views!!
                                                                                                      • Submitted: Jan 3, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Perfect Getaway Spot

                                                                                                      5 of 5
                                                                                                      We had 5 couples (all late 20s) stay for new years weekend and it was perfect! House was bigger than pictures make it look and we were all very comfortable. Beautiful view out the back windows of house as well. 15 minutes to Killington ski resort. Great weekend had by all! Highly recommend. Pat was very accessible leading up to our stay as well...thanks!
                                                                                                      • Submitted: Jan 3, 2017
                                                                                                      • Stayed: Dec 2016