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Additional fees apply. Taxes may be added.
    Wonderful! 4.8/5
    (20 reviews)
    avg/night
    Chalet #3935073
    • 6 BR
    • 5 BA
    • Sleeps 16
    20
    Viewed 34 times in the last 48 hours

    Confirmation within 24 hours

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

      House #4348210
      • 3 BR
      • 1 BA
      • 1 HF BA
      • Sleeps 6
      1

      Confirmation within 24 hours

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

        Exceptional! 5/5
        (10 reviews)
        avg/night
        Cottage #119135
        • 2 BR
        • 1 BA
        • Sleeps 5
        10
        Viewed 5 times in the last 48 hours

        Confirmation within 24 hours

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

          avg/night
          House #4102778
          • 3 BR
          • 2 BA
          • 2 HF BA
          • Sleeps 7
          4
          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
            (129 reviews)
            avg/night
            House #181030vb
            • 4 BR
            • 2 BA
            • Sleeps 10
            129
            Viewed 16 times in the last 48 hours

            Confirmation within 24 hours

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

              Exceptional! 5/5
              (18 reviews)
              avg/night
              Cottage #3563396
              • 5 BR
              • 4 BA
              • 1 HF BA
              • Sleeps 12
              18
              Viewed 24 times in the last 48 hours

              Confirmation within 24 hours

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

                Very Good! 4.2/5
                (35 reviews)
                avg/night
                Cabin #3772464
                • 3 BR
                • 2 BA
                • Sleeps 10
                35
                Viewed 19 times in the last 48 hours

                Confirmation within 24 hours

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

                  Cottage #576715vb
                  • 2 BR
                  • 1 BA
                  • Sleeps 9
                  6
                  Viewed 7 times in the last 48 hours

                  Instant confirmation

                  Your booking request will be confirmed immediately.

                    House #3994869
                    • 2 BR
                    • 1 BA
                    • 1 HF BA
                    • Sleeps 4
                    2
                    Viewed 9 times in the last 48 hours

                    Confirmation within 24 hours

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

                      House #577551vb
                      • 4 BR
                      • 3 BA
                      • Sleeps 14
                      34

                      Confirmation within 24 hours

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

                        Wonderful! 4.9/5
                        (7 reviews)
                        avg/night
                        Cottage #843324vb
                        • 2 BR
                        • 1 BA
                        • Sleeps 5
                        7
                        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
                          (6 reviews)
                          avg/night
                          House #972803vb
                          • 5 BR
                          • 4 BA
                          • Sleeps 10
                          6
                          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
                            (27 reviews)
                            avg/night
                            House #3993646
                            • 5 BR
                            • 3 BA
                            • 1 HF BA
                            • Sleeps 10
                            27
                            Viewed 28 times in the last 48 hours

                            Confirmation within 24 hours

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

                              Exceptional! 5/5
                              (135 reviews)
                              avg/night
                              House #24790vb
                              • 4 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 10
                              135
                              Viewed 19 times in the last 48 hours

                              Instant confirmation

                              Your booking request will be confirmed immediately.

                                House #772653vb
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                6

                                Confirmation within 24 hours

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

                                  Cottage #4199659
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 6
                                  4

                                  Confirmation within 24 hours

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

                                    Excellent! 4.7/5
                                    (10 reviews)
                                    avg/night
                                    House #812330vb
                                    • 3 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 9
                                    10
                                    Viewed 18 times in the last 48 hours

                                    Confirmation within 24 hours

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

                                      avg/night
                                      Cottage #573058vb
                                      • 3 BR
                                      • 1 BA
                                      • 1 HF BA
                                      • Sleeps 7
                                      4
                                      Viewed 16 times in the last 48 hours

                                      Confirmation within 24 hours

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

                                        avg/night
                                        House #952691vb
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6
                                        3
                                        Viewed 27 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
                                          (17 reviews)
                                          avg/night
                                          House #246335
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 6
                                          17
                                          Viewed 13 times in the last 48 hours

                                          Confirmation within 24 hours

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

                                            Wonderful! 4.8/5
                                            (23 reviews)
                                            avg/night
                                            Cabin #3023600
                                            • 3 BR
                                            • 1 BA
                                            • Sleeps 6
                                            23
                                            Viewed 31 times in the last 48 hours

                                            Confirmation within 24 hours

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

                                              Wonderful! 4.9/5
                                              (19 reviews)
                                              avg/night
                                              House #476575vb
                                              • 3 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 7
                                              19
                                              Viewed 16 times in the last 48 hours

                                              Confirmation within 24 hours

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

                                                Good! 3.8/5
                                                (4 reviews)
                                                avg/night
                                                Cabin #4226763
                                                • 2 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                4
                                                Viewed 56 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
                                                  (6 reviews)
                                                  avg/night
                                                  Cottage #137000
                                                  • 3 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  6
                                                  Viewed 10 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
                                                    Cabin #4238413
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 8
                                                    6
                                                    Viewed 51 times in the last 48 hours

                                                    Confirmation within 24 hours

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

                                                      House #4198935
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      1

                                                      Instant confirmation

                                                      Your booking request will be confirmed immediately.

                                                        House #1032679vb
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 7
                                                        2

                                                        Confirmation within 24 hours

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

                                                          Exceptional! 5/5
                                                          (28 reviews)
                                                          View details for price
                                                          Farmhouse #394406vb
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          28

                                                          Confirmation within 24 hours

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

                                                            Exceptional! 5/5
                                                            (10 reviews)
                                                            avg/night
                                                            Estate #3952690
                                                            • 6 BR
                                                            • 6 BA
                                                            • Sleeps 14
                                                            10
                                                            Viewed 15 times in the last 48 hours

                                                            Confirmation within 24 hours

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

                                                              avg/night
                                                              House #3995320
                                                              • 5 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              4
                                                              Viewed 5 times in the last 48 hours

                                                              Confirmation within 24 hours

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

                                                                Wonderful! 4.8/5
                                                                (29 reviews)
                                                                avg/night
                                                                Cabin #583641vb
                                                                • 3 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                29
                                                                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
                                                                  (18 reviews)
                                                                  avg/night
                                                                  Apartment #971040
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  18
                                                                  Viewed 10 times in the last 48 hours

                                                                  Confirmation within 24 hours

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

                                                                    avg/night
                                                                    Cottage #360242vb
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 7
                                                                    3
                                                                    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
                                                                      (7 reviews)
                                                                      avg/night
                                                                      House #748038vb
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      7
                                                                      Viewed 11 times in the last 48 hours

                                                                      Confirmation within 24 hours

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

                                                                        House #100657
                                                                        • 4 BR
                                                                        • 4 BA
                                                                        • Sleeps 8
                                                                        3

                                                                        Confirmation within 24 hours

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

                                                                          Exceptional! 5/5
                                                                          (6 reviews)
                                                                          avg/night
                                                                          Cottage #485000vb
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          6
                                                                          Viewed 18 times in the last 48 hours

                                                                          Confirmation within 24 hours

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

                                                                            Cottage #560958vb
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            4

                                                                            Confirmation within 24 hours

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

                                                                              Estate #4119181
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 12
                                                                              2
                                                                              Viewed 21 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                avg/night
                                                                                House #4484620
                                                                                • 11 BR
                                                                                • 3 BA
                                                                                • Sleeps 22
                                                                                Viewed 6 times in the last 48 hours

                                                                                Confirmation within 24 hours

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

                                                                                  Cottage #959160vb
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 6

                                                                                  Confirmation within 24 hours

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

                                                                                    Cottage #598404vb
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    2

                                                                                    Confirmation within 24 hours

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

                                                                                      House #4444874
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8

                                                                                      Confirmation within 24 hours

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

                                                                                        Cottage #979923
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        8

                                                                                        Confirmation within 24 hours

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

                                                                                          avg/night
                                                                                          House #1107033vb
                                                                                          • 5 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 9
                                                                                          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
                                                                                            (10 reviews)
                                                                                            $50
                                                                                            avg/night
                                                                                            House #3897308
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 10
                                                                                            10

                                                                                            Instant confirmation

                                                                                            Your booking request will be confirmed immediately.

                                                                                              House #711387vb
                                                                                              • 4 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 8
                                                                                              Viewed 7 times in the last 48 hours

                                                                                              Instant confirmation

                                                                                              Your booking request will be confirmed immediately.

                                                                                                Excellent! 4.6/5
                                                                                                (5 reviews)
                                                                                                avg/night
                                                                                                House #3733056
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                5

                                                                                                Confirmation within 24 hours

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

                                                                                                  avg/night
                                                                                                  House #4544362
                                                                                                  • 5 BR
                                                                                                  • 3 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 10
                                                                                                  Viewed 13 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Exceptional! 5/5
                                                                                                    (50 reviews)
                                                                                                    avg/night
                                                                                                    Castle #240837
                                                                                                    • 8 BR
                                                                                                    • 5 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 22
                                                                                                    50
                                                                                                    Viewed 98 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Exceptional! 5/5
                                                                                                      (5 reviews)
                                                                                                      avg/night
                                                                                                      House #3654599
                                                                                                      • 6 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 16
                                                                                                      5
                                                                                                      Viewed 13 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 63

                                                                                                      Winchendon Vacation Rentals (63)