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Additional fees apply. Taxes may be added.
    Exceptional! 5/5
    (12 reviews)
    avg/night
    • 5 BR
    • 3 BA
    • Sleeps 14
    House #345355ha
    12
    Viewed 45 times in the last 48 hours
      • 3 BR
      • 2 BA
      • Sleeps 20
      House #640519
      3
      Viewed 6 times in the last 48 hours
        Excellent! 4.7/5
        (13 reviews)
        avg/night
        • 5 BR
        • 3 BA
        • Sleeps 12
        House #334430ha
        13
        Viewed 8 times in the last 48 hours
          Wonderful! 4.8/5
          (12 reviews)
          avg/night
          • 5 BR
          • 2 BA
          • Sleeps 12
          House #622687
          12
            Wonderful! 4.8/5
            (25 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 10
            House #340808ha
            25
            Viewed 17 times in the last 48 hours
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Chalet #4335951ha
              3
              Viewed 7 times in the last 48 hours
                Excellent! 4.6/5
                (9 reviews)
                avg/night
                • 4 BR
                • 3 BA
                • Sleeps 10
                House #129127
                9
                Viewed 12 times in the last 48 hours
                  • 2 BR
                  • 1 BA
                  • Sleeps 8
                  Condo #868730
                  6
                    Excellent! 4.7/5
                    (11 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    Chalet #3642810ha
                    11
                    Viewed 6 times in the last 48 hours
                      • 3 BR
                      • 3 BA
                      • Sleeps 6
                      House #764994
                        Wonderful! 4.9/5
                        (9 reviews)
                        avg/night
                        • 3 BR
                        • 1 BA
                        • 1 HF BA
                        • Sleeps 8
                        House #429854
                        9
                        Viewed 5 times in the last 48 hours
                          Wonderful! 4.9/5
                          (57 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 15
                          House #148104
                          57
                          Viewed 6 times in the last 48 hours
                            • 5 BR
                            • 3 BA
                            • Sleeps 16
                            Condo #938633ha
                            2
                              avg/night
                              • 4 BR
                              • 2 BA
                              • Sleeps 11
                              House #759492
                              1
                              Viewed 13 times in the last 48 hours
                                Exceptional! 5/5
                                (12 reviews)
                                avg/night
                                • 5 BR
                                • 3 BA
                                • Sleeps 14
                                House #259766
                                12
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 8
                                  House #3861821ha
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 20
                                    House #8164567ha
                                      • 3 BR
                                      • 3 BA
                                      • Sleeps 6
                                      House #8164546ha
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 11
                                        House #8167865ha
                                          Wonderful! 4.9/5
                                          (41 reviews)
                                          avg/night
                                          • 5 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 13
                                          House #119086ha
                                          41
                                          Viewed 53 times in the last 48 hours
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            House #151465
                                            52
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 8
                                              Chalet #204550
                                              2
                                              Viewed 9 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (22 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 10
                                                House #166942
                                                22
                                                  Wonderful! 4.8/5
                                                  (9 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 3 BA
                                                  • 1 HF BA
                                                  • Sleeps 13
                                                  House #853465
                                                  9
                                                  Viewed 15 times in the last 48 hours
                                                    Wonderful! 4.8/5
                                                    (43 reviews)
                                                    avg/night
                                                    • 6 BR
                                                    • 3 BA
                                                    • Sleeps 32
                                                    House #76323
                                                    43
                                                    Viewed 18 times in the last 48 hours
                                                      Exceptional! 5/5
                                                      (8 reviews)
                                                      avg/night
                                                      • 6 BR
                                                      • 3 BA
                                                      • Sleeps 21
                                                      House #935042
                                                      8
                                                      Viewed 28 times in the last 48 hours
                                                        Exceptional! 5/5
                                                        (5 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Cabin #312902
                                                        5
                                                          Excellent! 4.7/5
                                                          (21 reviews)
                                                          avg/night
                                                          • 5 BR
                                                          • 2 BA
                                                          • Sleeps 22
                                                          House #94002
                                                          21
                                                          Viewed 41 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (28 reviews)
                                                            avg/night
                                                            • 5 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 15
                                                            House #3545103ha
                                                            28
                                                            Viewed 23 times in the last 48 hours
                                                              avg/night
                                                              • 5 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 10
                                                              House #868713
                                                              3
                                                              Viewed 6 times in the last 48 hours
                                                                Exceptional! 5/5
                                                                (11 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 13
                                                                House #644647
                                                                11
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • Sleeps 18
                                                                  House #4328491ha
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 10
                                                                    House #3861978ha
                                                                    4
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 9
                                                                      House #4355567ha
                                                                      Viewed 8 times in the last 48 hours
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        House #3837975ha
                                                                        1
                                                                        Viewed 11 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (21 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Farmhouse #394111
                                                                          21
                                                                          Viewed 16 times in the last 48 hours
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            House #263559ha
                                                                            25
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 10
                                                                              House #959109ha
                                                                                • 6 BR
                                                                                • 3 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 16
                                                                                House #209094ha
                                                                                28
                                                                                  Exceptional! 5/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 5
                                                                                  Chalet #645213
                                                                                  9
                                                                                  Viewed 7 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (11 reviews)
                                                                                    avg/night
                                                                                    • 5 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 12
                                                                                    House #956396ha
                                                                                    11
                                                                                    Viewed 13 times in the last 48 hours
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      House #264368ha
                                                                                      14
                                                                                        Exceptional! 5/5
                                                                                        (9 reviews)
                                                                                        avg/night
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 8
                                                                                        House #772545
                                                                                        9
                                                                                          • 4 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 12
                                                                                          House #651874
                                                                                          22
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 10
                                                                                            Farmhouse #3867434ha
                                                                                            2
                                                                                              Excellent! 4.7/5
                                                                                              (20 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 12
                                                                                              House #148363ha
                                                                                              20
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 8
                                                                                                House #331057
                                                                                                1
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  House #306812ha
                                                                                                  1
                                                                                                    Exceptional! 5/5
                                                                                                    (16 reviews)
                                                                                                    View details for price
                                                                                                    • 5 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 14
                                                                                                    Lodge #334087
                                                                                                    16
                                                                                                      Exceptional! 5/5
                                                                                                      (59 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 10
                                                                                                      House #217614
                                                                                                      59
                                                                                                      Viewed 10 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield: Condos, Chalets & More (300+)

                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Fantastic Vacation Rental

                                                                                                      5 of 5
                                                                                                      Our group absolutely loved this house. It is close to Killington, which is why we chose it. The kids and adults loved the spacious interior, as well as the hot tub. The hot tub worked great. I booked the rental and I didn't hear one complaint from any member of our group about the house. We look forward to booking this house again.
                                                                                                      • Submitted: Mar 26, 2017
                                                                                                      • Stayed: Mar 2017

                                                                                                      bigger than the pictures let on

                                                                                                      5 of 5
                                                                                                      My group and I had a fantastic weekend! We loved how it was close so Killington and yet set back enough in the woods to allow for some privacy. The house was much bigger than we expected, very clean and all instructions were posted. The hot tub was a real treat and it definitely works GREAT! Such a comfortable atmosphere. Thank you Mike!
                                                                                                      • Submitted: Mar 22, 2017
                                                                                                      • Stayed: Mar 2017

                                                                                                      Comfortable, cozy, nice views, good location! Great place

                                                                                                      5 of 5
                                                                                                      The house was very comfortable, very cozy, and 15 min drive from the ski resort ! We were a group of 9 friends, we stayed there 3 nights and we were all very happy! The views from the house are very nice ! I recommend this place !
                                                                                                      • Submitted: Mar 9, 2017
                                                                                                      • Stayed: Feb 2017