Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
  • Showing 1-50 of 300+
  View map Map
Additional fees apply. Taxes may be added.
    Exceptional! 5/5
    (13 reviews)
    avg/night
    House #345355
    • 5 BR
    • 3 BA
    • Sleeps 14
    13
    Viewed 42 times in the last 48 hours

    Confirmation within 24 hours

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

      Exceptional! 5/5
      (13 reviews)
      avg/night
      House #259766vb
      • 5 BR
      • 3 BA
      • Sleeps 14
      13
      Viewed 9 times in the last 48 hours

      Confirmation within 24 hours

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

        House #4328487
        • 3 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 6
        9

        Instant confirmation

        Your booking request will be confirmed immediately.

          Excellent! 4.7/5
          (13 reviews)
          avg/night
          House #334430
          • 5 BR
          • 3 BA
          • Sleeps 12
          13
          Viewed 15 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
            (59 reviews)
            avg/night
            House #148104vb
            • 3 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 15
            59
            Viewed 36 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
              (25 reviews)
              avg/night
              House #340808
              • 3 BR
              • 2 BA
              • Sleeps 10
              25
              Viewed 26 times in the last 48 hours

              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
                3
                Viewed 6 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 9 times in the last 48 hours

                  Confirmation within 24 hours

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

                    House #640519vb
                    • 3 BR
                    • 2 BA
                    • Sleeps 20
                    3
                    Viewed 36 times in the last 48 hours

                    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
                      Viewed 6 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

                        Confirmation within 24 hours

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

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

                          Instant confirmation

                          Your booking request will be confirmed immediately.

                            Excellent! 4.3/5
                            (6 reviews)
                            avg/night
                            Condo #868730vb
                            • 2 BR
                            • 1 BA
                            • Sleeps 8
                            6
                            Viewed 8 times in the last 48 hours

                            Instant confirmation

                            Your booking request will be confirmed immediately.

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

                              Instant confirmation

                              Your booking request will be confirmed immediately.

                                House #4615239
                                • 3 BR
                                • 2 BA
                                • Sleeps 6

                                Confirmation within 24 hours

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

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

                                  Instant confirmation

                                  Your booking request will be confirmed immediately.

                                    House #8167865
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 11

                                    Instant confirmation

                                    Your booking request will be confirmed immediately.

                                      avg/night
                                      House #8164567
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 20
                                      Viewed 7 times in the last 48 hours

                                      Instant confirmation

                                      Your booking request will be confirmed immediately.

                                        House #8164546
                                        • 3 BR
                                        • 3 BA
                                        • Sleeps 6

                                        Instant confirmation

                                        Your booking request will be confirmed immediately.

                                          Exceptional! 5/5
                                          (110 reviews)
                                          avg/night
                                          Cabin #176037
                                          • 2 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 5
                                          110
                                          Viewed 102 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
                                            Cabin #754153vb
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            11
                                            Viewed 36 times in the last 48 hours

                                            Confirmation within 24 hours

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

                                              Exceptional! 5/5
                                              (6 reviews)
                                              avg/night
                                              Cottage #4272059
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              6
                                              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
                                                (43 reviews)
                                                avg/night
                                                House #119086
                                                • 5 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 13
                                                43
                                                Viewed 56 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 #846796vb
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  5
                                                  Viewed 12 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
                                                    (18 reviews)
                                                    avg/night
                                                    Condo #4225962
                                                    • 2 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 6
                                                    18
                                                    Viewed 32 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
                                                      (89 reviews)
                                                      $96
                                                      avg/night
                                                      Condo #374633vb
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      89
                                                      Viewed 33 times in the last 48 hours

                                                      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
                                                        Viewed 15 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
                                                          (19 reviews)
                                                          avg/night
                                                          House #4086336
                                                          • 5 BR
                                                          • 3 BA
                                                          • Sleeps 18
                                                          19
                                                          Viewed 90 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
                                                            (17 reviews)
                                                            avg/night
                                                            Condo #967638vb
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            17
                                                            Viewed 26 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
                                                              (41 reviews)
                                                              avg/night
                                                              Condo #128197
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              41
                                                              Viewed 21 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
                                                                (20 reviews)
                                                                $83
                                                                avg/night
                                                                Condo #758489vb
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                20
                                                                Viewed 7 times in the last 48 hours

                                                                Instant confirmation

                                                                Your booking request will be confirmed immediately.

                                                                  Exceptional! 5/5
                                                                  (5 reviews)
                                                                  avg/night
                                                                  House #4203259
                                                                  • 1 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  5
                                                                  Viewed 17 times in the last 48 hours

                                                                  Confirmation within 24 hours

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

                                                                    Exceptional! 5/5
                                                                    (59 reviews)
                                                                    avg/night
                                                                    Farmhouse #3482379
                                                                    • 6 BR
                                                                    • 4 BA
                                                                    • Sleeps 12
                                                                    59
                                                                    Viewed 38 times in the last 48 hours

                                                                    Confirmation within 24 hours

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

                                                                      Exceptional! 5/5
                                                                      (12 reviews)
                                                                      avg/night
                                                                      House #440850vb
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      12
                                                                      Viewed 15 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
                                                                        (20 reviews)
                                                                        avg/night
                                                                        Condo #772841vb
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                        20
                                                                        Viewed 29 times in the last 48 hours

                                                                        Confirmation within 24 hours

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

                                                                          Exceptional! 5/5
                                                                          (42 reviews)
                                                                          avg/night
                                                                          House #3809315
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          42
                                                                          Viewed 24 times in the last 48 hours

                                                                          Confirmation within 24 hours

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

                                                                            Excellent! 4.6/5
                                                                            (16 reviews)
                                                                            avg/night
                                                                            House #104116
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            16
                                                                            Viewed 24 times in the last 48 hours

                                                                            Confirmation within 24 hours

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

                                                                              Exceptional! 5/5
                                                                              (22 reviews)
                                                                              avg/night
                                                                              House #125564
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 10
                                                                              22
                                                                              Viewed 18 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                Excellent! 4.4/5
                                                                                (23 reviews)
                                                                                avg/night
                                                                                Condo #264900
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                23
                                                                                Viewed 6 times in the last 48 hours

                                                                                Confirmation within 24 hours

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

                                                                                  Exceptional! 5/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  Apartment #4053247
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  6
                                                                                  Viewed 8 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
                                                                                    (10 reviews)
                                                                                    avg/night
                                                                                    House #853465vb
                                                                                    • 5 BR
                                                                                    • 3 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 13
                                                                                    10
                                                                                    Viewed 57 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
                                                                                      (52 reviews)
                                                                                      avg/night
                                                                                      House #971056
                                                                                      • 6 BR
                                                                                      • 4 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 14
                                                                                      52
                                                                                      Viewed 29 times in the last 48 hours

                                                                                      Confirmation within 24 hours

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

                                                                                        avg/night
                                                                                        Estate #888377vb
                                                                                        • 8 BR
                                                                                        • 8 BA
                                                                                        • 2 HF BA
                                                                                        • Sleeps 14
                                                                                        4
                                                                                        Viewed 33 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
                                                                                          (23 reviews)
                                                                                          $85
                                                                                          avg/night
                                                                                          House #112754
                                                                                          • 5 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 15
                                                                                          23
                                                                                          Viewed 37 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 31 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
                                                                                              Cabin #401479vb
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              23
                                                                                              Viewed 26 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
                                                                                                (19 reviews)
                                                                                                avg/night
                                                                                                Condo #780495vb
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                19
                                                                                                Viewed 12 times in the last 48 hours

                                                                                                Confirmation within 24 hours

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

                                                                                                  Wonderful! 4.8/5
                                                                                                  (11 reviews)
                                                                                                  avg/night
                                                                                                  Farmhouse #4018072
                                                                                                  • 7 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 28
                                                                                                  11
                                                                                                  Viewed 64 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Exceptional! 5/5
                                                                                                    (24 reviews)
                                                                                                    avg/night
                                                                                                    Farmhouse #3839959
                                                                                                    • 7 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 24
                                                                                                    24
                                                                                                    Viewed 51 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
                                                                                                      Cottage #3929442
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 8
                                                                                                      12
                                                                                                      Viewed 19 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+)