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  • Showing 1-50 of 300+
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    Wonderful! 4.9/5
    (27 reviews)
    avg/night
    House #420727vb
    • 3 BR
    • 2 BA
    • Sleeps 12
    27
    Viewed 27 times in the last 48 hours

    Confirmation within 24 hours

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

      Wonderful! 4.9/5
      (36 reviews)
      avg/night
      House #469617vb
      • 3 BR
      • 1 BA
      • Sleeps 6
      36
      Viewed 38 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
        (15 reviews)
        avg/night
        Cottage #203288vb
        • 3 BR
        • 1 BA
        • Sleeps 6
        15
        Viewed 31 times in the last 48 hours

        Confirmation within 24 hours

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

          avg/night
          Cottage #425380vb
          • 5 BR
          • 3 BA
          • Sleeps 8
          3
          Viewed 31 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
            (23 reviews)
            avg/night
            House #310035vb
            • 1 BR
            • 1 BA
            • Sleeps 4
            23
            Viewed 15 times in the last 48 hours

            Confirmation within 24 hours

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

              Good! 3.7/5
              (6 reviews)
              avg/night
              Cottage #310698
              • 2 BR
              • 1 BA
              • Sleeps 7
              6
              Viewed 16 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
                (15 reviews)
                avg/night
                Apartment #133082
                • 1 BR
                • 1 BA
                • Sleeps 4
                15
                Viewed 9 times in the last 48 hours

                Instant confirmation

                Your booking request will be confirmed immediately.

                  avg/night
                  Condo #878199vb
                  • 3 BR
                  • 3 BA
                  • Sleeps 13
                  2
                  Viewed 22 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
                    (10 reviews)
                    avg/night
                    Condo #595232vb
                    • 3 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 9
                    10
                    Viewed 10 times in the last 48 hours

                    Confirmation within 24 hours

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

                      Very Good! 4/5
                      (8 reviews)
                      avg/night
                      House #344576vb
                      • 3 BR
                      • 2 BA
                      • Sleeps 7
                      8
                      Viewed 16 times in the last 48 hours

                      Confirmation within 24 hours

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

                        Estate #802737vb
                        • 5 BR
                        • 3 BA
                        • 2 HF BA
                        • Sleeps 9
                        2
                        Viewed 28 times in the last 48 hours

                        Confirmation within 24 hours

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

                          avg/night
                          Townhome #4320036
                          • 4 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 10
                          2
                          Viewed 9 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
                            (23 reviews)
                            avg/night
                            House #251195vb
                            • 7 BR
                            • 3 BA
                            • Sleeps 18
                            23
                            Viewed 24 times in the last 48 hours

                            Confirmation within 24 hours

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

                              House #1020471vb
                              • 4 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 12
                              3
                              Viewed 59 times in the last 48 hours

                              Confirmation within 24 hours

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

                                avg/night
                                Apartment #1010923vb
                                • 2 BR
                                • 1 BA
                                • Sleeps 5
                                Viewed 18 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
                                  Apartment #615402vb
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 4
                                  4
                                  Viewed 13 times in the last 48 hours

                                  Confirmation within 24 hours

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

                                    avg/night
                                    House #985738vb
                                    • 8 BR
                                    • 5 BA
                                    • Sleeps 20
                                    Viewed 17 times in the last 48 hours

                                    Confirmation within 24 hours

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

                                      Townhome #4170111
                                      • 4 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 8

                                      Confirmation within 24 hours

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

                                        Condo #4365894
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4

                                        Confirmation within 24 hours

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

                                          Exceptional! 5/5
                                          (6 reviews)
                                          avg/night
                                          House #804956vb
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          6
                                          Viewed 44 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 #330190
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 7
                                            9
                                            Viewed 21 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
                                              Estate #4258796
                                              • 6 BR
                                              • 5 BA
                                              • Sleeps 20
                                              19
                                              Viewed 143 times in the last 48 hours

                                              Confirmation within 24 hours

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

                                                Exceptional! 5/5
                                                (9 reviews)
                                                avg/night
                                                Cottage #3790476
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                9
                                                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
                                                  (20 reviews)
                                                  avg/night
                                                  Cottage #707780vb
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 5
                                                  20
                                                  Viewed 40 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
                                                    (26 reviews)
                                                    avg/night
                                                    House #729783vb
                                                    • 5 BR
                                                    • 5 BA
                                                    • Sleeps 12
                                                    26
                                                    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
                                                      (10 reviews)
                                                      avg/night
                                                      Farmhouse #627684vb
                                                      • 4 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      10
                                                      Viewed 11 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
                                                        Chateau / Country House #4149878
                                                        • 3 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        10
                                                        Viewed 44 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
                                                          (8 reviews)
                                                          avg/night
                                                          Condo #3712818
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          8
                                                          Viewed 11 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
                                                            (38 reviews)
                                                            avg/night
                                                            Cottage #293009
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            38
                                                            Viewed 72 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
                                                              (5 reviews)
                                                              avg/night
                                                              Bungalow #717959vb
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              5
                                                              Viewed 16 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
                                                                (51 reviews)
                                                                avg/night
                                                                Cabin #182224
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                51
                                                                Viewed 65 times in the last 48 hours

                                                                Confirmation within 24 hours

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

                                                                  Exceptional! 5/5
                                                                  (14 reviews)
                                                                  avg/night
                                                                  Barn #616214vb
                                                                  • 5 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 10
                                                                  14
                                                                  Viewed 37 times in the last 48 hours

                                                                  Confirmation within 24 hours

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

                                                                    Wonderful! 4.8/5
                                                                    (21 reviews)
                                                                    avg/night
                                                                    House #236935vb
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    21
                                                                    Viewed 14 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 #272149vb
                                                                      • 3 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 10
                                                                      19
                                                                      Viewed 35 times in the last 48 hours

                                                                      Instant confirmation

                                                                      Your booking request will be confirmed immediately.

                                                                        Exceptional! 5/5
                                                                        (10 reviews)
                                                                        avg/night
                                                                        House #4064007
                                                                        • 6 BR
                                                                        • 3 BA
                                                                        • Sleeps 10
                                                                        10
                                                                        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
                                                                          (10 reviews)
                                                                          avg/night
                                                                          House #4193492
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          10
                                                                          Viewed 17 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
                                                                            (22 reviews)
                                                                            avg/night
                                                                            Cabin #189705vb
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            22
                                                                            Viewed 38 times in the last 48 hours

                                                                            Confirmation within 24 hours

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

                                                                              House #700566vb
                                                                              • 4 BR
                                                                              • 1 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              7

                                                                              Confirmation within 24 hours

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

                                                                                Exceptional! 5/5
                                                                                (5 reviews)
                                                                                avg/night
                                                                                House #4160350
                                                                                • 5 BR
                                                                                • 3 BA
                                                                                • Sleeps 8
                                                                                5
                                                                                Viewed 14 times in the last 48 hours

                                                                                Confirmation within 24 hours

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

                                                                                  Exceptional! 5/5
                                                                                  (17 reviews)
                                                                                  avg/night
                                                                                  Estate #629154vb
                                                                                  • 6 BR
                                                                                  • 4 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 12
                                                                                  17
                                                                                  Viewed 12 times in the last 48 hours

                                                                                  Confirmation within 24 hours

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

                                                                                    Excellent! 4.5/5
                                                                                    (13 reviews)
                                                                                    avg/night
                                                                                    House #3860654
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    13
                                                                                    Viewed 20 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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

                                                                                      Good! 3.9/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      Cottage #3576605
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 8
                                                                                      10
                                                                                      Viewed 20 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 #3811779
                                                                                        • 3 BR
                                                                                        • 1 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 8
                                                                                        16
                                                                                        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
                                                                                          (16 reviews)
                                                                                          avg/night
                                                                                          House #396147vb
                                                                                          • 6 BR
                                                                                          • 5 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 16
                                                                                          16
                                                                                          Viewed 69 times in the last 48 hours

                                                                                          Confirmation within 24 hours

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

                                                                                            Exceptional! 5/5
                                                                                            (17 reviews)
                                                                                            avg/night
                                                                                            House #583082vb
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 12
                                                                                            17
                                                                                            Viewed 40 times in the last 48 hours

                                                                                            Confirmation within 24 hours

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

                                                                                              Exceptional! 5/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              Lodge #3967190
                                                                                              • 7 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 24
                                                                                              9
                                                                                              Viewed 106 times in the last 48 hours

                                                                                              Confirmation within 24 hours

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

                                                                                                avg/night
                                                                                                House #4222851
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                Viewed 17 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
                                                                                                  (33 reviews)
                                                                                                  avg/night
                                                                                                  House #135474vb
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 3
                                                                                                  33
                                                                                                  Viewed 26 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
                                                                                                    (12 reviews)
                                                                                                    avg/night
                                                                                                    House #479396vb
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 7
                                                                                                    12
                                                                                                    Viewed 19 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Wonderful! 4.8/5
                                                                                                      (29 reviews)
                                                                                                      avg/night
                                                                                                      House #419897vb
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      29
                                                                                                      Viewed 9 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+)