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  • Showing 1-50 of 300+
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    House #345355
    • 5 BR
    • 3 BA
    • Sleeps 14
    10

    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.

        House #340808
        • 3 BR
        • 2 BA
        • Sleeps 10
        24

        Confirmation within 24 hours

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

          Exceptional! 5/5
          (7 reviews)
          avg/night
          House #129127vb
          • 4 BR
          • 3 BA
          • Sleeps 10
          7

          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.

              Chalet #4335951
              • 3 BR
              • 2 BA
              • Sleeps 8
              2

              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

                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.

                    Excellent! 4.7/5
                    (11 reviews)
                    avg/night
                    Chalet #3642810
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    11

                    Confirmation within 24 hours

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

                      House #148104vb
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 15
                      57

                      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

                        Confirmation within 24 hours

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

                          Condo #868730vb
                          • 2 BR
                          • 1 BA
                          • Sleeps 8
                          4

                          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.

                              Condo #938633
                              • 5 BR
                              • 3 BA
                              • Sleeps 16
                              2

                              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

                                      Confirmation within 24 hours

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

                                        Condo #104286
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 10
                                        5

                                        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

                                          Confirmation within 24 hours

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

                                            Condo #846796vb
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4
                                            4

                                            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

                                              Confirmation within 24 hours

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

                                                Apartment #4053247
                                                • 1 BR
                                                • 1 BA
                                                • Sleeps 4
                                                3

                                                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

                                                  Confirmation within 24 hours

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

                                                    Condo #628992vb
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    3

                                                    Confirmation within 24 hours

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

                                                      Condo #3840565
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4

                                                      Confirmation within 24 hours

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

                                                        Cottage #4272059
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        3

                                                        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

                                                          Confirmation within 24 hours

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

                                                            Condo #374633vb
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            85

                                                            Confirmation within 24 hours

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

                                                              Exceptional! 5/5
                                                              (6 reviews)
                                                              avg/night
                                                              Cottage #755454vb
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              6

                                                              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

                                                                Confirmation within 24 hours

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

                                                                  Farmhouse #3839959
                                                                  • 7 BR
                                                                  • 4 BA
                                                                  • Sleeps 24
                                                                  23

                                                                  Confirmation within 24 hours

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

                                                                    House #4086336
                                                                    • 5 BR
                                                                    • 3 BA
                                                                    • Sleeps 18
                                                                    13

                                                                    Confirmation within 24 hours

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

                                                                      Condo #758489vb
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      16

                                                                      Instant confirmation

                                                                      Your booking request will be confirmed immediately.

                                                                        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.

                                                                          House #411999vb
                                                                          • 2 BR
                                                                          • 3 BA
                                                                          • Sleeps 6
                                                                          32

                                                                          Confirmation within 24 hours

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

                                                                            Cottage #3929442
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 8
                                                                            9

                                                                            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

                                                                              Confirmation within 24 hours

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

                                                                                Condo #4225962
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 6
                                                                                10

                                                                                Confirmation within 24 hours

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

                                                                                  House #853465vb
                                                                                  • 5 BR
                                                                                  • 3 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 13
                                                                                  9

                                                                                  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

                                                                                    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

                                                                                      Confirmation within 24 hours

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

                                                                                        House #3992583
                                                                                        • 3 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 10
                                                                                        16

                                                                                        Confirmation within 24 hours

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

                                                                                          Condo #264900
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          19

                                                                                          Confirmation within 24 hours

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

                                                                                            Exceptional! 5/5
                                                                                            (55 reviews)
                                                                                            avg/night
                                                                                            Farmhouse #3482379
                                                                                            • 6 BR
                                                                                            • 4 BA
                                                                                            • Sleeps 12
                                                                                            55

                                                                                            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

                                                                                              Confirmation within 24 hours

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

                                                                                                Chalet #478821vb
                                                                                                • 5 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                10

                                                                                                Confirmation within 24 hours

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

                                                                                                  Condo #967638vb
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  9

                                                                                                  Confirmation within 24 hours

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

                                                                                                    House #125564
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 10
                                                                                                    21

                                                                                                    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.

                                                                                                      • 1 - 50 of 300+

                                                                                                      Pittsfield Vacation Rentals (300+)