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In the far south-eastern corner of Monmouthshire, holiday rental accommodation in Chepstow is not to be overlooked if you have a love of the great outdoors as you won't find a more breathtaking and easily accessible supply than awaits discovery right on the doorstep of any holiday cottage in Chepstow. Nestling amongst the outstanding natural beauty of the Wye Valley with views towards the majestic Black Mountains and close to where the historic Forest of Dean straddles the border of England and Wales, holiday accommodation in Chepstow will give you so many opportunities for sporting and recreational activities that you can be sure the whole family will find something to appeal to their sense of adventure in and around Chepstow - holiday cottages in Monmouthshire being chosen in locations throughout the region particularly by those with a passion for walking, cycling, horse-riding and bird-watching, although with so much architectural heritage scattered around these diverse landscapes, the interests of just about everybody will be catered for when you choose a holiday home rental in Chepstow, as the famous Tintern Abbey and a stunning medievel castle are enough to keep any history-buff happy. Close to the river Wye and within easy reach of at least two clubs with superb facilities for leisure and golf, holiday accommodation in Chepstow couldn't offer much more variety or versatility if it tried, so you really won't need to consider anywhere else for a family vacation rental to remember.

  • Showing 1-50 of 278
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    House #6892517
    • 3 BR
    • 3 BA
    • Sleeps 6
    2

    Confirmation within 24 hours

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

      Wonderful! 4.9/5
      (19 reviews)
      avg/night
      Cottage #6505330
      • 2 BR
      • 1 BA
      • Sleeps 4
      19
      Viewed 39 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
        (26 reviews)
        avg/night
        Bungalow #730799
        • 2 BR
        • 1 BA
        • Separate Toilet
        • Sleeps 6
        26
        Viewed 16 times in the last 48 hours

        Confirmation within 24 hours

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

          Wonderful! 4.8/5
          (8 reviews)
          avg/night
          Cottage #6024828
          • 2 BR
          • 1 BA
          • Sleeps 4
          8
          Viewed 10 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
            (28 reviews)
            avg/night
            Cottage #8126582
            • 2 BR
            • 2 BA
            • Sleeps 6
            28
            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
              (23 reviews)
              avg/night
              Barn #8137953
              • 1 BR
              • 1 BA
              • Sleeps 2
              23
              Viewed 21 times in the last 48 hours

              Confirmation within 24 hours

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

                Wonderful! 4.8/5
                (41 reviews)
                avg/night
                Cottage #8128998
                • 2 BR
                • 1 BA
                • Sleeps 4
                41
                Viewed 42 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
                  (21 reviews)
                  avg/night
                  House #1989892
                  • 4 BR
                  • 4 BA
                  • Sleeps 10
                  21
                  Viewed 32 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
                    Apartment #1870496
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    19
                    Viewed 25 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
                      Multiple rentals Barn #6781888
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      18
                      Viewed 98 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
                        (16 reviews)
                        avg/night
                        Cottage #8124698
                        • 3 BR
                        • 3 BA
                        • Sleeps 6
                        16
                        Viewed 22 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
                          (4 reviews)
                          avg/night
                          House #1598068
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          4
                          Viewed 9 times in the last 48 hours

                          Confirmation within 24 hours

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

                            Wonderful! 4.9/5
                            (8 reviews)
                            avg/night
                            Cottage #8089965
                            • 2 BR
                            • 1 BA
                            • Sleeps 4
                            8
                            Viewed 23 times in the last 48 hours

                            Confirmation within 24 hours

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

                              Multiple rentals House #8137766
                              • 4 BR
                              • 3 BA
                              • Sleeps 9
                              5
                              Viewed 24 times in the last 48 hours

                              Confirmation within 24 hours

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

                                Exceptional! 5/5
                                (14 reviews)
                                avg/night
                                Cottage #6710875
                                • 2 BR
                                • 1 BA
                                • Separate Toilet
                                • Sleeps 6
                                14
                                Viewed 36 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
                                  (14 reviews)
                                  avg/night
                                  Apartment #6104329
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 2
                                  14
                                  Viewed 22 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 #6522094
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    9
                                    Viewed 30 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
                                      (6 reviews)
                                      avg/night
                                      Barn #1874495
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      6
                                      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
                                        (7 reviews)
                                        avg/night
                                        Apartment #1832900
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        7
                                        Viewed 23 times in the last 48 hours

                                        Confirmation within 24 hours

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

                                          Multiple rentals Cottage #6781888
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 4
                                          1
                                          Viewed 29 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
                                            Cottage #8159302
                                            • 3 BR
                                            • 1 BA
                                            • Sleeps 6
                                            12
                                            Viewed 17 times in the last 48 hours

                                            Confirmation within 24 hours

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

                                              Exceptional! 5/5
                                              (11 reviews)
                                              avg/night
                                              Multiple rentals Barn #6781888
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              11
                                              Viewed 10 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
                                                (3 reviews)
                                                avg/night
                                                Cottage #8060087
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 4
                                                3
                                                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
                                                  (12 reviews)
                                                  avg/night
                                                  Farmhouse #6755518
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  12
                                                  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
                                                    (20 reviews)
                                                    avg/night
                                                    Cottage #8147896
                                                    • 1 BR
                                                    • 2 BA
                                                    • Sleeps 4
                                                    20
                                                    Viewed 13 times in the last 48 hours

                                                    Confirmation within 24 hours

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

                                                      Wonderful! 4.9/5
                                                      (11 reviews)
                                                      avg/night
                                                      Cottage #1880426
                                                      • 3 BR
                                                      • 1 BA
                                                      • Separate Toilet
                                                      • Sleeps 7
                                                      11
                                                      Viewed 27 times in the last 48 hours

                                                      Confirmation within 24 hours

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

                                                        Multiple rentals Cottage #1913408
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        3
                                                        Viewed 11 times in the last 48 hours

                                                        Confirmation within 24 hours

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

                                                          Exceptional! 5/5
                                                          (4 reviews)
                                                          avg/night
                                                          Multiple rentals House #410666
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 5
                                                          4
                                                          Viewed 5 times in the last 48 hours

                                                          Confirmation within 24 hours

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

                                                            Exceptional! 5/5
                                                            (4 reviews)
                                                            avg/night
                                                            Cottage #8153108
                                                            • 1 BR
                                                            • 1 BA
                                                            • Separate Toilet
                                                            • Sleeps 4
                                                            4
                                                            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
                                                              (4 reviews)
                                                              avg/night
                                                              Cottage #8076660
                                                              • 2 BR
                                                              • 2 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.

                                                                Cottage #8031311
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                36

                                                                Confirmation within 24 hours

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

                                                                  Wonderful! 4.9/5
                                                                  (9 reviews)
                                                                  avg/night
                                                                  Apartment #426254
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4
                                                                  9
                                                                  Viewed 6 times in the last 48 hours

                                                                  Confirmation within 24 hours

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

                                                                    Wonderful! 4.8/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    Cabin #8079609
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    5
                                                                    Viewed 37 times in the last 48 hours

                                                                    Confirmation within 24 hours

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

                                                                      Excellent! 4.3/5
                                                                      (6 reviews)
                                                                      avg/night
                                                                      Cottage #6813948
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      6
                                                                      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
                                                                        (6 reviews)
                                                                        avg/night
                                                                        Apartment #6781621
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 2
                                                                        6

                                                                        Confirmation within 24 hours

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

                                                                          Cottage #1969185
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 2

                                                                          Instant confirmation

                                                                          Your booking request will be confirmed immediately.

                                                                            Cottage #6491809
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            2

                                                                            Confirmation within 24 hours

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

                                                                              Exceptional! 5/5
                                                                              (5 reviews)
                                                                              avg/night
                                                                              House #8134255
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 5
                                                                              5
                                                                              Viewed 11 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                Multiple rentals House #8137766
                                                                                • 4 BR
                                                                                • 1 BA
                                                                                • Sleeps 9
                                                                                Viewed 5 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
                                                                                  (7 reviews)
                                                                                  avg/night
                                                                                  House #1587648
                                                                                  • 6 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 14
                                                                                  7
                                                                                  Viewed 33 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
                                                                                    Cottage #8160756
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    5
                                                                                    Viewed 12 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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

                                                                                      Wonderful! 4.8/5
                                                                                      (5 reviews)
                                                                                      avg/night
                                                                                      Barn #493322
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 4
                                                                                      5
                                                                                      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
                                                                                        (9 reviews)
                                                                                        avg/night
                                                                                        House #838758
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • Separate Toilet
                                                                                        • Sleeps 9
                                                                                        9
                                                                                        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 #6789190
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Viewed 13 times in the last 48 hours

                                                                                          Confirmation within 24 hours

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

                                                                                            Cottage #1964363
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • Sleeps 8

                                                                                            Instant confirmation

                                                                                            Your booking request will be confirmed immediately.

                                                                                              Exceptional! 5/5
                                                                                              (6 reviews)
                                                                                              avg/night
                                                                                              Cottage #8166366
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 4
                                                                                              6
                                                                                              Viewed 6 times in the last 48 hours

                                                                                              Confirmation within 24 hours

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

                                                                                                avg/night
                                                                                                Cottage #6509450
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 4
                                                                                                1
                                                                                                Viewed 6 times in the last 48 hours

                                                                                                Instant confirmation

                                                                                                Your booking request will be confirmed immediately.

                                                                                                  avg/night
                                                                                                  House #6864805
                                                                                                  • 6 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 10
                                                                                                  Viewed 15 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Cottage #8049840
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 7
                                                                                                    1
                                                                                                    Viewed 21 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Wonderful! 4.8/5
                                                                                                      (13 reviews)
                                                                                                      avg/night
                                                                                                      Cottage #8123500
                                                                                                      • 3 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 6
                                                                                                      13
                                                                                                      Viewed 48 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 278

                                                                                                      Holiday Accommodation Chepstow (278)