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  • Showing 1-50 of 253
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (6 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 10
    House #129127vb
    6
    Viewed 26 times in the last 48 hours
      Exceptional! 5.0/5
      (10 reviews)
      avg/night
      • 5 BR
      • 3 BA
      • Sleeps 14
      House #345355
      10
      Viewed 38 times in the last 48 hours
        Wonderful! 4.9/5
        (23 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 10
        House #340808
        23
        Viewed 55 times in the last 48 hours
          Excellent! 4.6/5
          (11 reviews)
          avg/night
          • 5 BR
          • 3 BA
          • Sleeps 12
          House #334430
          11
          Viewed 76 times in the last 48 hours
            • 2 BR
            • 1 BA
            • Sleeps 8
            House #868730vb
            1
            Viewed 30 times in the last 48 hours
              avg/night
              • 4 BR
              • 2 BA
              • Sleeps 11
              House #759492vb
              0
              Viewed 28 times in the last 48 hours
                Wonderful! 4.9/5
                (57 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 15
                House #148104vb
                57
                Viewed 5 times in the last 48 hours
                  Wonderful! 4.8/5
                  (11 reviews)
                  avg/night
                  • 5 BR
                  • 2 BA
                  • Sleeps 12
                  House #622687vb
                  11
                  Viewed 15 times in the last 48 hours
                    Wonderful! 4.8/5
                    (21 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 10
                    House #166942vb
                    21
                    Viewed 90 times in the last 48 hours
                      Wonderful! 4.9/5
                      (9 reviews)
                      avg/night
                      • 3 BR
                      • 1 BA
                      • 1 HF BA
                      • Sleeps 8
                      House #429854vb
                      9
                        avg/night
                        • 4 BR
                        • 2 BA
                        • Sleeps 8
                        House #3861821
                        0
                        Viewed 10 times in the last 48 hours
                          • 3 BR
                          • 3 BA
                          • Sleeps 6
                          House #764994vb
                          0
                          Viewed 39 times in the last 48 hours
                            Excellent! 4.7/5
                            (9 reviews)
                            View details for price
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 6
                            House #4328487
                            9
                              Exceptional! 5.0/5
                              (10 reviews)
                              avg/night
                              • 5 BR
                              • 3 BA
                              • Sleeps 14
                              House #259766vb
                              10
                              Viewed 13 times in the last 48 hours
                                Wonderful! 4.8/5
                                (48 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                House #151465vb
                                48
                                Viewed 74 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (37 reviews)
                                  avg/night
                                  • 5 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 13
                                  House #119086
                                  37
                                  Viewed 97 times in the last 48 hours
                                    avg/night
                                    • 6 BR
                                    • 3 BA
                                    • Sleeps 21
                                    House #935042vb
                                    3
                                    Viewed 93 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (23 reviews)
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #263559
                                      23
                                      Viewed 45 times in the last 48 hours
                                        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
                                          Viewed 28 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (7 reviews)
                                            avg/night
                                            • 5 BR
                                            • 3 BA
                                            • 1 HF BA
                                            • Sleeps 13
                                            House #853465vb
                                            7
                                            Viewed 52 times in the last 48 hours
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                              House #3837975
                                              1
                                              Viewed 18 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (7 reviews)
                                                avg/night
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 6
                                                House #772545vb
                                                7
                                                Viewed 45 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (38 reviews)
                                                  avg/night
                                                  • 6 BR
                                                  • 3 BA
                                                  • Sleeps 32
                                                  House #76323vb
                                                  38
                                                  Viewed 96 times in the last 48 hours
                                                    avg/night
                                                    • 5 BR
                                                    • 2 BA
                                                    • 1 HF BA
                                                    • Sleeps 10
                                                    House #868713vb
                                                    2
                                                    Viewed 22 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (10 reviews)
                                                      avg/night
                                                      • 4 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 13
                                                      House #644647vb
                                                      10
                                                      Viewed 31 times in the last 48 hours
                                                        avg/night
                                                        • 4 BR
                                                        • 3 BA
                                                        • 2 HF BA
                                                        • Sleeps 12
                                                        House #4216957
                                                        3
                                                        Viewed 84 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (55 reviews)
                                                          avg/night
                                                          • 4 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 10
                                                          House #217614vb
                                                          55
                                                          Viewed 64 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (13 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 8
                                                            House #264368
                                                            13
                                                            Viewed 13 times in the last 48 hours
                                                              • 4 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 11
                                                              House #918418vb
                                                              2
                                                              Viewed 30 times in the last 48 hours
                                                                avg/night
                                                                • 4 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                House #3861978
                                                                3
                                                                Viewed 35 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (18 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 10
                                                                  House #10877vb
                                                                  18
                                                                  Viewed 77 times in the last 48 hours
                                                                    Very Good! 4.1/5
                                                                    (11 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 6
                                                                    House #126984
                                                                    11
                                                                    Viewed 9 times in the last 48 hours
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • Sleeps 18
                                                                      House #4328491
                                                                      0
                                                                      Viewed 87 times in the last 48 hours
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        House #959109
                                                                        0
                                                                        Viewed 32 times in the last 48 hours
                                                                          Exceptional! 5.0/5
                                                                          (20 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 12
                                                                          House #651874vb
                                                                          20
                                                                          Viewed 57 times in the last 48 hours
                                                                            Excellent! 4.6/5
                                                                            (18 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 3 BA
                                                                            • Sleeps 12
                                                                            House #148363
                                                                            18
                                                                            Viewed 23 times in the last 48 hours
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 3 BA
                                                                              • Sleeps 12
                                                                              House #200427
                                                                              3
                                                                              Viewed 64 times in the last 48 hours
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                House #988098vb
                                                                                0
                                                                                Viewed 62 times in the last 48 hours
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  House #868701vb
                                                                                  4
                                                                                  Viewed 30 times in the last 48 hours
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 12
                                                                                    House #4329162
                                                                                    1
                                                                                    Viewed 66 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (13 reviews)
                                                                                      avg/night
                                                                                      • 5 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 16
                                                                                      House #662431vb
                                                                                      13
                                                                                      Viewed 30 times in the last 48 hours
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 6
                                                                                        House #868696vb
                                                                                        4
                                                                                        Viewed 49 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (7 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 7
                                                                                          House #868692vb
                                                                                          7
                                                                                          Viewed 10 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (14 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 11
                                                                                            House #937557
                                                                                            14
                                                                                            Viewed 49 times in the last 48 hours
                                                                                              Very Good! 4.0/5
                                                                                              (6 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              House #868706vb
                                                                                              6
                                                                                              Viewed 58 times in the last 48 hours
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 10
                                                                                                House #4064899
                                                                                                2
                                                                                                Viewed 17 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (12 reviews)
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 7
                                                                                                  House #393827vb
                                                                                                  12
                                                                                                  Viewed 24 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (21 reviews)
                                                                                                    avg/night
                                                                                                    • 10 BR
                                                                                                    • 3 BA
                                                                                                    • 2 HF BA
                                                                                                    • Sleeps 16
                                                                                                    House #147901vb
                                                                                                    21
                                                                                                    Viewed 48 times in the last 48 hours
                                                                                                      Exceptional! 5.0/5
                                                                                                      (6 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 9
                                                                                                      House #4055252
                                                                                                      6
                                                                                                      Viewed 40 times in the last 48 hours
                                                                                                      • 1 - 50 of 253

                                                                                                      Pittsfield: House Rentals (253)

                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      One of those rare finds on Homeaway...

                                                                                                      5 of 5
                                                                                                      This is really a spectacular house, and we knew there would be some good views, but little did we know just how good. You really feel like you are on top of the world up there with views of seemingly all the major peaks within a hundred miles. Everything about the house would appear to be like new - you would have thought we were the first ones to use it. The driveway would be very intimidating if there had been snow/ice, however it's also clear that the owner is ready to go out of his way to help with this, whether via the caretaker who lives right below the house, rapid plowing/sanding service, or the spare truck in the garage with chains on the tires that could be used to shuttle people up the driveway if needed. Everyone should try to stay here at least once!
                                                                                                      • Submitted: Jan 16, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      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

                                                                                                      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