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Stokesley self-catering accommodation is set in and around a charming market town on the fringe of the North York Moors. Despite being found in breathtaking countryside, the town is only a few miles from Middlesbrough, one of the most important urban areas on the Northeast coast. So this means that all the amenities you could possibly need at a Stokesley holiday cottage are within easy reach. The landscape here is nothing short of stunning, with huge expanses of scenic heather moorland a little way south. An ideal for a spot for a walk nearby is the unusual Rosebury Topping Hill. This sandstone landform offers wonderful views of the area from its summit as is found no more than a few miles from holiday homes in Stokesley. If you fancy a day at the beach during your trip to a cottage in Stokesley there are some beautiful stretches of sandy beach on the coast a few miles away. Redcar and Saltburn are particularly appealling. The resort at Saltburn has some wonderful 19th Century features like a water-powered funicular railway that carries visitors from the cliff-top to the beach. For a spot of shopping, Middlesbrough is within minutes of Stokesley holiday rentals and offers a wealth of high street stores, with a couple of large shopping centers as well. A site of historical interest close to Stokesley holiday accommodation can be found at the nearby village of Great Ayton, where the famous English explorer Captain James Cook spent much of his formative years. A small museum, monument and the family home can all be visited here. Weather At a Stokesley self-catering cottage you’ll most likely experience mild summers and relatively cool winters. In the warmest months you can expect plenty of sunshine and less rainfall. Best Time to Visit The summer months are the best time to head for Stokesley rental cottages, as this is when you can expect slightly more clement temperatures, ideal for long walks and outdoor fun. Reaching Stokesley The nearest international airport to Stokesley self-catering holiday homes and cottages is Durham Tees Valley (MME), which is about 16 miles away and is served by a number of low-cost carriers.

  • Showing 1-50 of 300+
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    Wonderful! 4.9/5
    (15 reviews)
    avg/night
    Chateau / Country House #8115706
    • 8 BR
    • 5 BA
    • Sleeps 17
    15
    Viewed 48 times in the last 48 hours

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      Apartment #6897915
      • 1 BR
      • 1 BA
      • Sleeps 2

      Instant confirmation

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        Exceptional! 5/5
        (20 reviews)
        avg/night
        Cottage #8052258
        • 2 BR
        • 1 BA
        • Sleeps 4
        20
        Viewed 186 times in the last 48 hours

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          Exceptional! 5/5
          (23 reviews)
          avg/night
          Cottage #1989698
          • 1 BR
          • 1 BA
          • Sleeps 2
          23
          Viewed 71 times in the last 48 hours

          Confirmation within 24 hours

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            Wonderful! 4.8/5
            (13 reviews)
            avg/night
            Cottage #8248
            • 4 BR
            • 2 BA
            • Separate Toilet
            • Sleeps 8
            13
            Viewed 56 times in the last 48 hours

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              Excellent! 4.3/5
              (12 reviews)
              avg/night
              Multiple rentals Mobile Home #8107865
              • 3 BR
              • 1 BA
              • Sleeps 6
              12
              Viewed 101 times in the last 48 hours

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                Excellent! 4.7/5
                (26 reviews)
                avg/night
                Barn #1867699
                • 2 BR
                • 2 BA
                • Sleeps 5
                26
                Viewed 37 times in the last 48 hours

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                  Excellent! 4.7/5
                  (11 reviews)
                  avg/night
                  Cottage #1881241
                  • 2 BR
                  • 2 BA
                  • Sleeps 4
                  11
                  Viewed 52 times in the last 48 hours

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                    Exceptional! 5/5
                    (22 reviews)
                    avg/night
                    Cottage #1950049
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                    22
                    Viewed 66 times in the last 48 hours

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                      Wonderful! 4.8/5
                      (10 reviews)
                      avg/night
                      Cottage #6750222
                      • 2 BR
                      • 1 BA
                      • Sleeps 3
                      10
                      Viewed 43 times in the last 48 hours

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                        Excellent! 4.7/5
                        (11 reviews)
                        avg/night
                        Barn #8161980
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        11
                        Viewed 21 times in the last 48 hours

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                          Excellent! 4.4/5
                          (8 reviews)
                          avg/night
                          Cottage #8037757
                          • 3 BR
                          • 2 BA
                          • Sleeps 7
                          8
                          Viewed 30 times in the last 48 hours

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                            Wonderful! 4.9/5
                            (35 reviews)
                            avg/night
                            Cottage #1159360
                            • 3 BR
                            • 1 BA
                            • Sleeps 6
                            35
                            Viewed 46 times in the last 48 hours

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                              Excellent! 4.5/5
                              (10 reviews)
                              avg/night
                              Cottage #6759436
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              10
                              Viewed 37 times in the last 48 hours

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                                Excellent! 4.5/5
                                (12 reviews)
                                avg/night
                                Cottage #8159031
                                • 1 BR
                                • 1 BA
                                • Sleeps 2
                                12
                                Viewed 34 times in the last 48 hours

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                                  Excellent! 4.6/5
                                  (8 reviews)
                                  avg/night
                                  Cottage #1853870
                                  • 3 BR
                                  • 1 BA
                                  • Sleeps 5
                                  8
                                  Viewed 20 times in the last 48 hours

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                                    Wonderful! 4.9/5
                                    (35 reviews)
                                    avg/night
                                    House #8168579
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    35
                                    Viewed 10 times in the last 48 hours

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                                      Very Good! 4.2/5
                                      (10 reviews)
                                      avg/night
                                      Caravan #1869375
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      10
                                      Viewed 51 times in the last 48 hours

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                                        Wonderful! 4.8/5
                                        (4 reviews)
                                        avg/night
                                        Cottage #1990530
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        4
                                        Viewed 12 times in the last 48 hours

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                                          Wonderful! 4.9/5
                                          (10 reviews)
                                          avg/night
                                          Cottage #8156522
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          10
                                          Viewed 20 times in the last 48 hours

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                                            Wonderful! 4.9/5
                                            (13 reviews)
                                            avg/night
                                            Cottage #1032741
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 8
                                            13
                                            Viewed 11 times in the last 48 hours

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                                              Exceptional! 5/5
                                              (4 reviews)
                                              avg/night
                                              Cottage #6488244
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              4
                                              Viewed 13 times in the last 48 hours

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                                                Wonderful! 4.8/5
                                                (9 reviews)
                                                avg/night
                                                Apartment #6729391
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 5
                                                9
                                                Viewed 10 times in the last 48 hours

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                                                  Exceptional! 5/5
                                                  (7 reviews)
                                                  avg/night
                                                  Bungalow #6710586
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 4
                                                  7
                                                  Viewed 12 times in the last 48 hours

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                                                    Excellent! 4.4/5
                                                    (11 reviews)
                                                    avg/night
                                                    Cottage #8111579
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    11
                                                    Viewed 41 times in the last 48 hours

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                                                      Excellent! 4.7/5
                                                      (23 reviews)
                                                      avg/night
                                                      Apartment #1203280
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 5
                                                      23
                                                      Viewed 11 times in the last 48 hours

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

                                                        Wonderful! 4.8/5
                                                        (4 reviews)
                                                        avg/night
                                                        Cottage #6513233
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        4
                                                        Viewed 34 times in the last 48 hours

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                                                          Exceptional! 5/5
                                                          (20 reviews)
                                                          avg/night
                                                          Cottage #8119427
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          20
                                                          Viewed 22 times in the last 48 hours

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                                                            Excellent! 4.7/5
                                                            (6 reviews)
                                                            avg/night
                                                            Cottage #8090645
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 2
                                                            6
                                                            Viewed 25 times in the last 48 hours

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                                                              Wonderful! 4.9/5
                                                              (18 reviews)
                                                              avg/night
                                                              House #8156298
                                                              • 4 BR
                                                              • 1 BA
                                                              • Sleeps 6
                                                              18
                                                              Viewed 19 times in the last 48 hours

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

                                                                Exceptional! 5/5
                                                                (5 reviews)
                                                                avg/night
                                                                Cottage #8171985
                                                                • 3 BR
                                                                • 1 BA
                                                                • Separate Toilet
                                                                • Sleeps 6
                                                                5
                                                                Viewed 23 times in the last 48 hours

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                                                                  avg/night
                                                                  Bungalow #6771706
                                                                  • 5 BR
                                                                  • 6 BA
                                                                  • Sleeps 11
                                                                  1
                                                                  Viewed 17 times in the last 48 hours

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                                                                    Excellent! 4.7/5
                                                                    (7 reviews)
                                                                    avg/night
                                                                    Cottage #8045250
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • Sleeps 8
                                                                    7
                                                                    Viewed 27 times in the last 48 hours

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                                                                      Exceptional! 5/5
                                                                      (5 reviews)
                                                                      avg/night
                                                                      Cottage #8077359
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      5
                                                                      Viewed 19 times in the last 48 hours

                                                                      Confirmation within 24 hours

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                                                                        House #6770318
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        3
                                                                        Viewed 36 times in the last 48 hours

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

                                                                          Wonderful! 4.8/5
                                                                          (4 reviews)
                                                                          avg/night
                                                                          House #1882725
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                          4
                                                                          Viewed 16 times in the last 48 hours

                                                                          Confirmation within 24 hours

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                                                                            Cottage #6932348
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Viewed 17 times in the last 48 hours

                                                                            Confirmation within 24 hours

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                                                                              Excellent! 4.5/5
                                                                              (11 reviews)
                                                                              avg/night
                                                                              Cottage #8150793
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 5
                                                                              11
                                                                              Viewed 22 times in the last 48 hours

                                                                              Confirmation within 24 hours

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

                                                                                avg/night
                                                                                Cottage #1967501
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 4
                                                                                Viewed 11 times in the last 48 hours

                                                                                Instant confirmation

                                                                                Your booking request will be confirmed immediately.

                                                                                  Excellent! 4.6/5
                                                                                  (5 reviews)
                                                                                  avg/night
                                                                                  Cottage #8170918
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 5
                                                                                  5
                                                                                  Viewed 13 times in the last 48 hours

                                                                                  Confirmation within 24 hours

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                                                                                    Apartment #8173574
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 2
                                                                                    2
                                                                                    Viewed 8 times in the last 48 hours

                                                                                    Confirmation within 24 hours

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                                                                                      Apartment #6810985
                                                                                      • 2 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 4
                                                                                      1
                                                                                      Viewed 25 times in the last 48 hours

                                                                                      Confirmation within 24 hours

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                                                                                        Multiple rentals Caravan #8107865
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Viewed 67 times in the last 48 hours

                                                                                        Confirmation within 24 hours

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                                                                                          Cottage #1850736
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          Viewed 15 times in the last 48 hours

                                                                                          Confirmation within 24 hours

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                                                                                            Multiple rentals Cottage #8102876
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8
                                                                                            2
                                                                                            Viewed 13 times in the last 48 hours

                                                                                            Confirmation within 24 hours

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                                                                                              Wonderful! 4.8/5
                                                                                              (4 reviews)
                                                                                              avg/night
                                                                                              Cottage #8154390
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              4
                                                                                              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
                                                                                                (13 reviews)
                                                                                                avg/night
                                                                                                House #8161389
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 8
                                                                                                13
                                                                                                Viewed 23 times in the last 48 hours

                                                                                                Confirmation within 24 hours

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                                                                                                  House #1906441
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 9
                                                                                                  2
                                                                                                  Viewed 15 times in the last 48 hours

                                                                                                  Confirmation within 24 hours

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                                                                                                    Excellent! 4.7/5
                                                                                                    (9 reviews)
                                                                                                    avg/night
                                                                                                    Cottage #8045259
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 5
                                                                                                    9
                                                                                                    Viewed 26 times in the last 48 hours

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Multiple rentals Cottage #8124143
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      5
                                                                                                      Viewed 16 times in the last 48 hours

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+