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    Exceptional! 5/5
    (5 reviews)
    $74
    avg/night
    Cottage #8113984
    • 2 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 4
    5
    Viewed 19 times in the last 48 hours
    This property does not have any reviews yet.

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.
      Wonderful! 4.9/5
      (9 reviews)
      $107
      avg/night
      Cottage #8171985
      • 3 BR
      • 1 BA
      • 1 HF BA
      • Sleeps 6
      9
      Viewed 11 times in the last 48 hours
      This property does not have any reviews yet.

      Instant confirmation

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        Wonderful! 4.9/5
        (24 reviews)
        $129
        avg/night
        House #8156298
        • 4 BR
        • 1 BA
        • Sleeps 6
        24
        Viewed 17 times in the last 48 hours
        This property does not have any reviews yet.

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.
          $228
          avg/night
          Multiple rentals Cottage #8102876
          • 4 BR
          • 1 BA
          • Sleeps 8
          2
          Viewed 16 times in the last 48 hours
          This property does not have any reviews yet.

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.
            $74
            avg/night
            Apartment #8173574
            • 1 BR
            • 1 BA
            • Sleeps 2
            4
            Viewed 15 times in the last 48 hours
            This property does not have any reviews yet.

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.
              Exceptional! 5/5
              (9 reviews)
              $111
              avg/night
              Bungalow #6710586
              • 2 BR
              • 2 BA
              • Sleeps 4
              9
              Viewed 8 times in the last 48 hours
              This property does not have any reviews yet.

              Confirmation within 24 hours

              Your booking request will be confirmed or denied within 24 hours.
                $81
                avg/night
                Multiple rentals Cottage #8102876
                • 2 BR
                • 1 BA
                • Sleeps 4
                1
                Viewed 21 times in the last 48 hours
                This property does not have any reviews yet.

                Confirmation within 24 hours

                Your booking request will be confirmed or denied within 24 hours.
                  $93
                  avg/night
                  Cottage #1964170
                  • 4 BR
                  • Sleeps 11
                  Viewed 7 times in the last 48 hours
                  This property does not have any reviews yet.

                  Instant confirmation

                  Your booking request will be confirmed immediately.
                    $197
                    avg/night
                    Cottage #1690832
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    This property does not have any reviews yet.

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.
                      $69
                      avg/night
                      Cottage #6932211
                      • 3 BR
                      • 1 BA
                      • Sleeps 5
                      This property does not have any reviews yet.

                      Instant confirmation

                      Your booking request will be confirmed immediately.
                        $112
                        avg/night
                        House #6976585
                        • 3 BR
                        • 1 BA
                        • 1 HF BA
                        • Sleeps 6
                        1
                        Viewed 14 times in the last 48 hours
                        This property does not have any reviews yet.

                        Instant confirmation

                        Your booking request will be confirmed immediately.
                          $172
                          avg/night
                          Cottage #8129799
                          • 4 BR
                          • 3 BA
                          • Sleeps 8
                          1
                          Viewed 7 times in the last 48 hours
                          This property does not have any reviews yet.

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.
                            $93
                            avg/night
                            Cottage #1976602
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            Viewed 8 times in the last 48 hours
                            This property does not have any reviews yet.

                            Confirmation within 24 hours

                            Your booking request will be confirmed or denied within 24 hours.
                              $108
                              avg/night
                              Cottage #1985148
                              • 2 BR
                              • 2 HF BA
                              • Sleeps 4
                              This property does not have any reviews yet.

                              Instant confirmation

                              Your booking request will be confirmed immediately.
                                $146
                                avg/night
                                Cottage #8168917
                                • 3 BR
                                • 3 HF BA
                                • Sleeps 6
                                This property does not have any reviews yet.

                                Instant confirmation

                                Your booking request will be confirmed immediately.
                                  $125
                                  avg/night
                                  Cottage #1862844
                                  • 4 BR
                                  • 1 HF BA
                                  • Sleeps 6
                                  This property does not have any reviews yet.

                                  Instant confirmation

                                  Your booking request will be confirmed immediately.
                                    $89
                                    avg/night
                                    Cottage #1865198
                                    • 2 BR
                                    • 3 BA
                                    • Sleeps 4
                                    This property does not have any reviews yet.

                                    Instant confirmation

                                    Your booking request will be confirmed immediately.
                                      $117
                                      avg/night
                                      Cottage #1865046
                                      • 2 BR
                                      • 1 HF BA
                                      • Sleeps 4
                                      This property does not have any reviews yet.

                                      Instant confirmation

                                      Your booking request will be confirmed immediately.
                                        $74
                                        avg/night
                                        Cottage #1858996
                                        • 2 BR
                                        • 1 HF BA
                                        • Sleeps 3
                                        This property does not have any reviews yet.

                                        Instant confirmation

                                        Your booking request will be confirmed immediately.
                                          $83
                                          avg/night
                                          Cottage #1857719
                                          • 3 BR
                                          • 1 HF BA
                                          • Sleeps 6
                                          This property does not have any reviews yet.

                                          Instant confirmation

                                          Your booking request will be confirmed immediately.
                                            View details for price
                                            Cottage #1865110
                                            • 3 BR
                                            • 3 HF BA
                                            • Sleeps 6
                                            This property does not have any reviews yet.

                                            Instant confirmation

                                            Your booking request will be confirmed immediately.
                                              $61
                                              avg/night
                                              Cottage #1967119
                                              • 2 BR
                                              • Sleeps 4
                                              Viewed 8 times in the last 48 hours
                                              This property does not have any reviews yet.

                                              Instant confirmation

                                              Your booking request will be confirmed immediately.
                                                $82
                                                avg/night
                                                Cottage #6066022
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                This property does not have any reviews yet.

                                                Instant confirmation

                                                Your booking request will be confirmed immediately.
                                                  $86
                                                  avg/night
                                                  Cottage #8197709
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  This property does not have any reviews yet.

                                                  Instant confirmation

                                                  Your booking request will be confirmed immediately.
                                                    $77
                                                    avg/night
                                                    Cottage #6506804
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    This property does not have any reviews yet.

                                                    Instant confirmation

                                                    Your booking request will be confirmed immediately.
                                                      $59
                                                      avg/night
                                                      Cottage #8345793
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 3
                                                      Viewed 9 times in the last 48 hours
                                                      This property does not have any reviews yet.

                                                      Instant confirmation

                                                      Your booking request will be confirmed immediately.
                                                        $103
                                                        avg/night
                                                        Cottage #8347278
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        Viewed 5 times in the last 48 hours
                                                        This property does not have any reviews yet.

                                                        Instant confirmation

                                                        Your booking request will be confirmed immediately.
                                                          Wonderful! 4.9/5
                                                          (46 reviews)
                                                          $90
                                                          avg/night
                                                          Cabin #8173995
                                                          • 1 BR
                                                          • Sleeps 2
                                                          46
                                                          Viewed 126 times in the last 48 hours
                                                          This property does not have any reviews yet.

                                                          Confirmation within 24 hours

                                                          Your booking request will be confirmed or denied within 24 hours.
                                                            Excellent! 4.4/5
                                                            (25 reviews)
                                                            $145
                                                            avg/night
                                                            Cottage #8046126
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            25
                                                            Viewed 43 times in the last 48 hours
                                                            This property does not have any reviews yet.

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.
                                                              Excellent! 4.6/5
                                                              (37 reviews)
                                                              $76
                                                              avg/night
                                                              Cottage #1890512
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              37
                                                              Viewed 43 times in the last 48 hours
                                                              This property does not have any reviews yet.

                                                              Confirmation within 24 hours

                                                              Your booking request will be confirmed or denied within 24 hours.
                                                                Wonderful! 4.8/5
                                                                (22 reviews)
                                                                $117
                                                                avg/night
                                                                Cottage #8248
                                                                • 4 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 8
                                                                22
                                                                Viewed 54 times in the last 48 hours
                                                                This property does not have any reviews yet.

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.
                                                                  Wonderful! 4.8/5
                                                                  (39 reviews)
                                                                  $89
                                                                  avg/night
                                                                  Cottage #8171140
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  39
                                                                  Viewed 62 times in the last 48 hours
                                                                  This property does not have any reviews yet.

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.
                                                                    Exceptional! 5/5
                                                                    (35 reviews)
                                                                    $91
                                                                    avg/night
                                                                    Cottage #1989698
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    35
                                                                    Viewed 49 times in the last 48 hours
                                                                    This property does not have any reviews yet.

                                                                    Instant confirmation

                                                                    Your booking request will be confirmed immediately.
                                                                      Wonderful! 4.9/5
                                                                      (12 reviews)
                                                                      $96
                                                                      avg/night
                                                                      Cottage #6551716
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 4
                                                                      12
                                                                      Viewed 13 times in the last 48 hours
                                                                      This property does not have any reviews yet.

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.
                                                                        Exceptional! 5/5
                                                                        (21 reviews)
                                                                        $98
                                                                        avg/night
                                                                        House #6730247
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        21
                                                                        Viewed 49 times in the last 48 hours
                                                                        This property does not have any reviews yet.

                                                                        Confirmation within 24 hours

                                                                        Your booking request will be confirmed or denied within 24 hours.
                                                                          Excellent! 4.5/5
                                                                          (15 reviews)
                                                                          $106
                                                                          avg/night
                                                                          Cottage #6759436
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 4
                                                                          15
                                                                          Viewed 71 times in the last 48 hours
                                                                          This property does not have any reviews yet.

                                                                          Confirmation within 24 hours

                                                                          Your booking request will be confirmed or denied within 24 hours.
                                                                            Exceptional! 5/5
                                                                            (32 reviews)
                                                                            $147
                                                                            avg/night
                                                                            House #8073148
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            32
                                                                            Viewed 27 times in the last 48 hours
                                                                            This property does not have any reviews yet.

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.
                                                                              Wonderful! 4.9/5
                                                                              (42 reviews)
                                                                              $89
                                                                              avg/night
                                                                              Cottage #1159360
                                                                              • 3 BR
                                                                              • 1 BA
                                                                              • Sleeps 6
                                                                              42
                                                                              Viewed 82 times in the last 48 hours
                                                                              This property does not have any reviews yet.

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.
                                                                                Exceptional! 5/5
                                                                                (31 reviews)
                                                                                $93
                                                                                avg/night
                                                                                Cottage #1950049
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                31
                                                                                Viewed 46 times in the last 48 hours
                                                                                This property does not have any reviews yet.

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.
                                                                                  Excellent! 4.7/5
                                                                                  (6 reviews)
                                                                                  $64
                                                                                  avg/night
                                                                                  Cottage #1990530
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  6
                                                                                  Viewed 14 times in the last 48 hours
                                                                                  This property does not have any reviews yet.

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.
                                                                                    Excellent! 4.7/5
                                                                                    (33 reviews)
                                                                                    $149
                                                                                    avg/night
                                                                                    Barn #1867699
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    33
                                                                                    Viewed 38 times in the last 48 hours
                                                                                    This property does not have any reviews yet.

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.
                                                                                      Excellent! 4.7/5
                                                                                      (19 reviews)
                                                                                      $73
                                                                                      avg/night
                                                                                      Cottage #8095231
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      19
                                                                                      Viewed 20 times in the last 48 hours
                                                                                      This property does not have any reviews yet.

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.
                                                                                        Wonderful! 4.8/5
                                                                                        (14 reviews)
                                                                                        $79
                                                                                        avg/night
                                                                                        Barn #8161980
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        14
                                                                                        Viewed 14 times in the last 48 hours
                                                                                        This property does not have any reviews yet.

                                                                                        Confirmation within 24 hours

                                                                                        Your booking request will be confirmed or denied within 24 hours.
                                                                                          Exceptional! 5/5
                                                                                          (15 reviews)
                                                                                          $103
                                                                                          avg/night
                                                                                          Barn #8130690
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          15
                                                                                          Viewed 9 times in the last 48 hours
                                                                                          This property does not have any reviews yet.

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.
                                                                                            Wonderful! 4.8/5
                                                                                            (10 reviews)
                                                                                            $163
                                                                                            avg/night
                                                                                            Cottage #6776082
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 4
                                                                                            10
                                                                                            Viewed 20 times in the last 48 hours
                                                                                            This property does not have any reviews yet.

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.
                                                                                              Wonderful! 4.9/5
                                                                                              (8 reviews)
                                                                                              $34
                                                                                              avg/night
                                                                                              Cottage #8051459
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              8
                                                                                              Viewed 43 times in the last 48 hours
                                                                                              This property does not have any reviews yet.

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.
                                                                                                Wonderful! 4.8/5
                                                                                                (6 reviews)
                                                                                                $94
                                                                                                avg/night
                                                                                                Cottage #8126935
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                6
                                                                                                Viewed 23 times in the last 48 hours
                                                                                                This property does not have any reviews yet.

                                                                                                Confirmation within 24 hours

                                                                                                Your booking request will be confirmed or denied within 24 hours.
                                                                                                  Wonderful! 4.8/5
                                                                                                  (28 reviews)
                                                                                                  $76
                                                                                                  avg/night
                                                                                                  Cottage #8155295
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  28
                                                                                                  Viewed 29 times in the last 48 hours
                                                                                                  This property does not have any reviews yet.

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.
                                                                                                    Wonderful! 4.8/5
                                                                                                    (13 reviews)
                                                                                                    $113
                                                                                                    avg/night
                                                                                                    Multiple rentals Cottage #8151859
                                                                                                    • 2 BR
                                                                                                    • Sleeps 4
                                                                                                    13
                                                                                                    Viewed 12 times in the last 48 hours
                                                                                                    This property does not have any reviews yet.

                                                                                                    Confirmation within 24 hours

                                                                                                    Your booking request will be confirmed or denied within 24 hours.
                                                                                                      Exceptional! 5/5
                                                                                                      (5 reviews)
                                                                                                      $274
                                                                                                      avg/night
                                                                                                      Cottage #6958961
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 8
                                                                                                      5
                                                                                                      Viewed 58 times in the last 48 hours
                                                                                                      This property does not have any reviews yet.

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Helmsley Vacation Rentals (300+)

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