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Pittsfield: Condos, Houses & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (10 reviews)
    avg/night
    • 5 BR
    • 3 BA
    • Sleeps 14
    House #345355
    10
    Viewed 22 times in the last 48 hours
      • 2 BR
      • 1 BA
      • Sleeps 8
      House #868730vb
      1
      Viewed 7 times in the last 48 hours
        Wonderful! 4.9/5
        (23 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 10
        House #340808
        23
        Viewed 32 times in the last 48 hours
          • 3 BR
          • 2 BA
          • Sleeps 20
          Chalet #640519vb
          2
          Viewed 25 times in the last 48 hours
            Exceptional! 5.0/5
            (6 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Sleeps 10
            House #129127vb
            6
            Viewed 32 times in the last 48 hours
              Excellent! 4.6/5
              (10 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Sleeps 12
              House #334430
              10
              Viewed 18 times in the last 48 hours
                Wonderful! 4.8/5
                (10 reviews)
                avg/night
                • 5 BR
                • 2 BA
                • Sleeps 12
                House #622687vb
                10
                Viewed 10 times in the last 48 hours
                  Wonderful! 4.8/5
                  (9 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 8
                  Chalet #3642810
                  9
                  Viewed 9 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
                    Viewed 6 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 7 times in the last 48 hours
                        avg/night
                        • 4 BR
                        • 2 BA
                        • Sleeps 11
                        House #759492vb
                        Viewed 35 times in the last 48 hours
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          Chalet #4335951
                          Viewed 148 times in the last 48 hours
                            Exceptional! 5.0/5
                            (86 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • 1 HF BA
                            • Sleeps 5
                            Cabin #176037
                            86
                            Viewed 70 times in the last 48 hours
                              Wonderful! 4.8/5
                              (9 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 4
                              Cabin #754153vb
                              9
                              Viewed 12 times in the last 48 hours
                                Excellent! 4.6/5
                                (5 reviews)
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                Condo #104286
                                5
                                Viewed 73 times in the last 48 hours
                                  avg/night
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 6
                                  Condo #628992vb
                                  1
                                  Viewed 22 times in the last 48 hours
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Condo #3840565
                                    Viewed 33 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (31 reviews)
                                      avg/night
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                      House #3809315
                                      31
                                      Viewed 54 times in the last 48 hours
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Apartment #4053247
                                        2
                                        Viewed 13 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (12 reviews)
                                          avg/night
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Condo #4053986
                                          12
                                          Viewed 21 times in the last 48 hours
                                            Excellent! 4.4/5
                                            (13 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 10
                                            Townhome #3484922
                                            13
                                            Viewed 15 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (12 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Condo #758489vb
                                              12
                                              Viewed 12 times in the last 48 hours
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                Cottage #4272059
                                                2
                                                Viewed 16 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (17 reviews)
                                                  avg/night
                                                  • 5 BR
                                                  • 3 BA
                                                  • 2 HF BA
                                                  • Sleeps 17
                                                  Lodge #3782397
                                                  17
                                                  Viewed 19 times in the last 48 hours
                                                    Excellent! 4.7/5
                                                    (80 reviews)
                                                    avg/night
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Condo #374633vb
                                                    80
                                                    Viewed 12 times in the last 48 hours
                                                      Excellent! 4.7/5
                                                      (11 reviews)
                                                      avg/night
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 12
                                                      Chalet #788299vb
                                                      11
                                                      Viewed 19 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (18 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Cabin #401479vb
                                                        18
                                                        Viewed 27 times in the last 48 hours
                                                          • 5 BR
                                                          • 2 BA
                                                          • Sleeps 7
                                                          House #495543vb
                                                          4
                                                            Exceptional! 5.0/5
                                                            (21 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 10
                                                            House #125564
                                                            21
                                                            Viewed 9 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (13 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              Chalet #3992583
                                                              13
                                                              Viewed 67 times in the last 48 hours
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 4
                                                                Condo #846796vb
                                                                3
                                                                  Excellent! 4.6/5
                                                                  (14 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 2 BA
                                                                  • Sleeps 18
                                                                  House #112754
                                                                  14
                                                                  Viewed 20 times in the last 48 hours
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    Condo #3837341
                                                                    6
                                                                    Viewed 28 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (9 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 7
                                                                      House #258826vb
                                                                      9
                                                                      Viewed 9 times in the last 48 hours
                                                                        Excellent! 4.6/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        Cottage #256292
                                                                        5
                                                                        Viewed 7 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (11 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Apartment #499330vb
                                                                          11
                                                                          Viewed 7 times in the last 48 hours
                                                                            Excellent! 4.4/5
                                                                            (14 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Condo #264900
                                                                            14
                                                                            Viewed 34 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (13 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 1 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              Lodge #432099vb
                                                                              13
                                                                                Wonderful! 4.8/5
                                                                                (9 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • Sleeps 8
                                                                                Cottage #3929442
                                                                                9
                                                                                Viewed 6 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 9
                                                                                  House #4055252
                                                                                  6
                                                                                  Viewed 23 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (28 reviews)
                                                                                    avg/night
                                                                                    • 7 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 19
                                                                                    House #137934
                                                                                    28
                                                                                    Viewed 33 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                      Chalet #204550vb
                                                                                      1
                                                                                      Viewed 12 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (21 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Condo #117502
                                                                                        21
                                                                                        Viewed 36 times in the last 48 hours
                                                                                          Excellent! 4.6/5
                                                                                          (5 reviews)
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 3 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 13
                                                                                          House #853465vb
                                                                                          5
                                                                                          Viewed 39 times in the last 48 hours
                                                                                            • 1 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 4
                                                                                            House #4203259
                                                                                            3
                                                                                            Viewed 15 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (17 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              Condo #446305vb
                                                                                              17
                                                                                              Viewed 28 times in the last 48 hours
                                                                                                Wonderful! 4.8/5
                                                                                                (20 reviews)
                                                                                                avg/night
                                                                                                • 10 BR
                                                                                                • 3 BA
                                                                                                • 2 HF BA
                                                                                                • Sleeps 16
                                                                                                House #147901vb
                                                                                                20
                                                                                                Viewed 18 times in the last 48 hours
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Condo #268757vb
                                                                                                  3
                                                                                                  Viewed 36 times in the last 48 hours
                                                                                                    Excellent! 4.7/5
                                                                                                    (10 reviews)
                                                                                                    avg/night
                                                                                                    • 5 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 10
                                                                                                    Chalet #478821vb
                                                                                                    10
                                                                                                    Viewed 7 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (17 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      House #618168vb
                                                                                                      17
                                                                                                      Viewed 19 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      A great stay

                                                                                                      4 of 5
                                                                                                      I thoroughly enjoyed the stay at the condo. Everything was clean and super convenient. I can't think of how it could have been any better or easier. Will definitely come stay again.
                                                                                                      • Submitted: Nov 30, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Amazing mountain escape!

                                                                                                      5 of 5
                                                                                                      We had the pleasure of staying at the lodge over a long weekend in October, with three other families (5 kids total). Wow! What an amazing home, in a breathtaking setting. The home is very large and modern, yet cozy at the same time. Plenty of room inside and out for the kids to run around and play. The kids particularly enjoyed the game room downstairs, while the adults enjoyed the hot tub. We all enjoyed searching for the hidden room (which we found, and the kids got a real kick out of). The house is fully stocked with games, towels and linens, and pots and pans - we really didn't need to bring a thing other than food. The lodge is conveniently located to hiking, wineries, breweries, etc. Kris (the owner) is great and always very responsive to questions. Needless to say, we did not want to leave, and look forward to staying here again!
                                                                                                      • Submitted: Nov 29, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Wonderful than my thought

                                                                                                      5 of 5
                                                                                                      The house is a really great place to stay for a ski vacation and the owner is very friendly and helpful. Looking forward for another visit in the future
                                                                                                      • Submitted: Nov 29, 2016
                                                                                                      • Stayed: Nov 2016