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  • Showing 1-50 of 300+
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    Exceptional! 5/5
    (10 reviews)
    avg/night
    House #345355
    • 5 BR
    • 3 BA
    • Sleeps 14
    10
    Viewed 22 times in the last 48 hours

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      Exceptional! 5/5
      (10 reviews)
      avg/night
      House #259766vb
      • 5 BR
      • 3 BA
      • Sleeps 14
      10

      Confirmation within 24 hours

      Your booking request will be confirmed or denied within 24 hours.

        Wonderful! 4.8/5
        (24 reviews)
        avg/night
        House #340808
        • 3 BR
        • 2 BA
        • Sleeps 10
        24
        Viewed 23 times in the last 48 hours

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.

          Chalet #640519vb
          • 3 BR
          • 2 BA
          • Sleeps 20
          2

          Instant confirmation

          Your booking request will be confirmed immediately.

            Exceptional! 5/5
            (6 reviews)
            avg/night
            House #129127vb
            • 4 BR
            • 3 BA
            • Sleeps 10
            6
            Viewed 5 times in the last 48 hours

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              Excellent! 4.7/5
              (12 reviews)
              avg/night
              House #334430
              • 5 BR
              • 3 BA
              • Sleeps 12
              12

              Confirmation within 24 hours

              Your booking request will be confirmed or denied within 24 hours.

                avg/night
                Chalet #4335951
                • 3 BR
                • 2 BA
                • Sleeps 8
                2
                Viewed 7 times in the last 48 hours

                Confirmation within 24 hours

                Your booking request will be confirmed or denied within 24 hours.

                  Wonderful! 4.8/5
                  (12 reviews)
                  avg/night
                  House #622687vb
                  • 5 BR
                  • 2 BA
                  • Sleeps 12
                  12
                  Viewed 6 times in the last 48 hours

                  Confirmation within 24 hours

                  Your booking request will be confirmed or denied within 24 hours.

                    Excellent! 4.7/5
                    (11 reviews)
                    avg/night
                    Chalet #3642810
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    11
                    Viewed 7 times in the last 48 hours

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.

                      Wonderful! 4.9/5
                      (57 reviews)
                      avg/night
                      House #148104vb
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 15
                      57
                      Viewed 5 times in the last 48 hours

                      Confirmation within 24 hours

                      Your booking request will be confirmed or denied within 24 hours.

                        Wonderful! 4.8/5
                        (21 reviews)
                        avg/night
                        House #166942vb
                        • 3 BR
                        • 2 BA
                        • Sleeps 10
                        21
                        Viewed 12 times in the last 48 hours

                        Confirmation within 24 hours

                        Your booking request will be confirmed or denied within 24 hours.

                          Wonderful! 4.9/5
                          (9 reviews)
                          avg/night
                          House #429854vb
                          • 3 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 8
                          9
                          Viewed 5 times in the last 48 hours

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            Wonderful! 4.8/5
                            (4 reviews)
                            avg/night
                            Condo #868730vb
                            • 2 BR
                            • 1 BA
                            • Sleeps 8
                            4
                            Viewed 9 times in the last 48 hours

                            Instant confirmation

                            Your booking request will be confirmed immediately.

                              House #759492vb
                              • 4 BR
                              • 2 BA
                              • Sleeps 11
                              1

                              Instant confirmation

                              Your booking request will be confirmed immediately.

                                avg/night
                                Condo #938633
                                • 5 BR
                                • 3 BA
                                • Sleeps 16
                                2
                                Viewed 9 times in the last 48 hours

                                Confirmation within 24 hours

                                Your booking request will be confirmed or denied within 24 hours.

                                  House #764994vb
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6

                                  Instant confirmation

                                  Your booking request will be confirmed immediately.

                                    House #3861821
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      Excellent! 4.7/5
                                      (9 reviews)
                                      View details for price
                                      House #4328487
                                      • 3 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      9

                                      Confirmation within 24 hours

                                      Your booking request will be confirmed or denied within 24 hours.

                                        Exceptional! 5/5
                                        (97 reviews)
                                        avg/night
                                        Cabin #176037
                                        • 2 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 5
                                        97
                                        Viewed 101 times in the last 48 hours

                                        Confirmation within 24 hours

                                        Your booking request will be confirmed or denied within 24 hours.

                                          Excellent! 4.6/5
                                          (5 reviews)
                                          avg/night
                                          Condo #104286
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 10
                                          5
                                          Viewed 27 times in the last 48 hours

                                          Confirmation within 24 hours

                                          Your booking request will be confirmed or denied within 24 hours.

                                            Wonderful! 4.8/5
                                            (39 reviews)
                                            avg/night
                                            House #119086
                                            • 5 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 13
                                            39
                                            Viewed 62 times in the last 48 hours

                                            Confirmation within 24 hours

                                            Your booking request will be confirmed or denied within 24 hours.

                                              Excellent! 4.5/5
                                              (4 reviews)
                                              avg/night
                                              Condo #846796vb
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 4
                                              4
                                              Viewed 52 times in the last 48 hours

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                Wonderful! 4.8/5
                                                (9 reviews)
                                                avg/night
                                                Cabin #754153vb
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                9
                                                Viewed 36 times in the last 48 hours

                                                Confirmation within 24 hours

                                                Your booking request will be confirmed or denied within 24 hours.

                                                  avg/night
                                                  Apartment #4053247
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  2
                                                  Viewed 19 times in the last 48 hours

                                                  Confirmation within 24 hours

                                                  Your booking request will be confirmed or denied within 24 hours.

                                                    Wonderful! 4.9/5
                                                    (36 reviews)
                                                    avg/night
                                                    House #3809315
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    36
                                                    Viewed 16 times in the last 48 hours

                                                    Confirmation within 24 hours

                                                    Your booking request will be confirmed or denied within 24 hours.

                                                      avg/night
                                                      Condo #628992vb
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      3
                                                      Viewed 19 times in the last 48 hours

                                                      Confirmation within 24 hours

                                                      Your booking request will be confirmed or denied within 24 hours.

                                                        Condo #3840565
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        Viewed 9 times in the last 48 hours

                                                        Confirmation within 24 hours

                                                        Your booking request will be confirmed or denied within 24 hours.

                                                          Excellent! 4.5/5
                                                          (15 reviews)
                                                          avg/night
                                                          House #104116
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          15
                                                          Viewed 24 times in the last 48 hours

                                                          Confirmation within 24 hours

                                                          Your booking request will be confirmed or denied within 24 hours.

                                                            Excellent! 4.7/5
                                                            (85 reviews)
                                                            avg/night
                                                            Condo #374633vb
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            85
                                                            Viewed 20 times in the last 48 hours

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.

                                                              avg/night
                                                              Cottage #4272059
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              3
                                                              Viewed 26 times in the last 48 hours

                                                              Confirmation within 24 hours

                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                Exceptional! 5/5
                                                                (19 reviews)
                                                                avg/night
                                                                Cabin #401479vb
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                19
                                                                Viewed 39 times in the last 48 hours

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                  Exceptional! 5/5
                                                                  (23 reviews)
                                                                  avg/night
                                                                  Farmhouse #3839959
                                                                  • 7 BR
                                                                  • 4 BA
                                                                  • Sleeps 24
                                                                  23
                                                                  Viewed 37 times in the last 48 hours

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                    Wonderful! 4.9/5
                                                                    (16 reviews)
                                                                    avg/night
                                                                    Condo #758489vb
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    16
                                                                    Viewed 12 times in the last 48 hours

                                                                    Instant confirmation

                                                                    Your booking request will be confirmed immediately.

                                                                      Wonderful! 4.8/5
                                                                      (12 reviews)
                                                                      avg/night
                                                                      House #4086336
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • Sleeps 18
                                                                      12
                                                                      Viewed 84 times in the last 48 hours

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        Exceptional! 5/5
                                                                        (4 reviews)
                                                                        avg/night
                                                                        House #495543vb
                                                                        • 5 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        4

                                                                        Confirmation within 24 hours

                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                          Exceptional! 5/5
                                                                          (32 reviews)
                                                                          avg/night
                                                                          House #411999vb
                                                                          • 2 BR
                                                                          • 3 BA
                                                                          • Sleeps 6
                                                                          32
                                                                          Viewed 8 times in the last 48 hours

                                                                          Confirmation within 24 hours

                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                            Excellent! 4.6/5
                                                                            (16 reviews)
                                                                            avg/night
                                                                            House #112754
                                                                            • 5 BR
                                                                            • 2 BA
                                                                            • Sleeps 15
                                                                            16
                                                                            Viewed 32 times in the last 48 hours

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                              Wonderful! 4.8/5
                                                                              (9 reviews)
                                                                              avg/night
                                                                              Cottage #3929442
                                                                              • 3 BR
                                                                              • 1 BA
                                                                              • Sleeps 8
                                                                              9
                                                                              Viewed 18 times in the last 48 hours

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                Exceptional! 5/5
                                                                                (53 reviews)
                                                                                avg/night
                                                                                Apartment #354330
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                53
                                                                                Viewed 20 times in the last 48 hours

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  Wonderful! 4.8/5
                                                                                  (9 reviews)
                                                                                  avg/night
                                                                                  Condo #4225962
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6
                                                                                  9
                                                                                  Viewed 24 times in the last 48 hours

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    Wonderful! 4.8/5
                                                                                    (9 reviews)
                                                                                    avg/night
                                                                                    House #853465vb
                                                                                    • 5 BR
                                                                                    • 3 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 13
                                                                                    9
                                                                                    Viewed 28 times in the last 48 hours

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                      Wonderful! 4.8/5
                                                                                      (39 reviews)
                                                                                      avg/night
                                                                                      Condo #128197
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 6
                                                                                      39
                                                                                      Viewed 51 times in the last 48 hours

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                        Exceptional! 5/5
                                                                                        (16 reviews)
                                                                                        avg/night
                                                                                        House #3992583
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 10
                                                                                        16
                                                                                        Viewed 40 times in the last 48 hours

                                                                                        Confirmation within 24 hours

                                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                                          Excellent! 4.5/5
                                                                                          (19 reviews)
                                                                                          avg/night
                                                                                          Condo #264900
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          19
                                                                                          Viewed 16 times in the last 48 hours

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                                            Wonderful! 4.9/5
                                                                                            (13 reviews)
                                                                                            avg/night
                                                                                            Lodge #432099vb
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 8
                                                                                            13
                                                                                            Viewed 30 times in the last 48 hours

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              Excellent! 4.7/5
                                                                                              (10 reviews)
                                                                                              avg/night
                                                                                              Chalet #478821vb
                                                                                              • 5 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 10
                                                                                              10
                                                                                              Viewed 13 times in the last 48 hours

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                Wonderful! 4.9/5
                                                                                                (9 reviews)
                                                                                                avg/night
                                                                                                Condo #967638vb
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                9
                                                                                                Viewed 12 times in the last 48 hours

                                                                                                Confirmation within 24 hours

                                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                                  Exceptional! 5/5
                                                                                                  (25 reviews)
                                                                                                  avg/night
                                                                                                  Lodge #263450vb
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 14
                                                                                                  25
                                                                                                  Viewed 36 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                                    Condo #268757vb
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    5

                                                                                                    Confirmation within 24 hours

                                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                                      Wonderful! 4.8/5
                                                                                                      (16 reviews)
                                                                                                      avg/night
                                                                                                      Chalet #788299vb
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 12
                                                                                                      16
                                                                                                      Viewed 24 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield Vacation Rentals (300+)