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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 3 BA
    • Sleeps 6
    House #6892517
      • 1 BR
      • 1 BA
      • Sleeps 2
      Cottage #8010888
        • 3 BR
        • 3 BA
        • Sleeps 8
        Cottage #6880439
        4
          Exceptional! 5.0/5
          (6 reviews)
          $68
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 2
          Apartment #6781621
          6
            • 1 BR
            • Sleeps 2
            Cottage #8160756
            5
              • 1 BR
              • 1 BA
              • Sleeps 2
              Apartment #6560147
              2 Reviews
                • 2 BR
                • 2 BA
                • Sleeps 4
                Barn #1689669
                  • 2 BR
                  • 1 BA
                  • Sleeps 4
                  Cottage #8060087
                  3
                    • 2 BR
                    • 1 BA
                    • Sleeps 4
                    Multiple rentals Cottage #8137394
                    6
                      • 2 BR
                      • 1 BA
                      • Sleeps 4
                      Cottage #8128998
                      38
                        • 1 BR
                        • Sleeps 2
                        Multiple rentals Barn #8137394
                        9
                          • 3 BR
                          • 2 BA
                          • Sleeps 5
                          Barn #8071320
                          2 Reviews
                            • 1 BR
                            • 1 BA
                            • Sleeps 2
                            Cottage #1969185
                              • 3 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 4
                              Cottage #1124523
                              1 Review
                                • 3 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 5
                                Cottage #1124509
                                  • 3 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 7
                                  Cottage #8146235
                                  2 Reviews
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 6
                                    Cottage #8126582
                                    23
                                      Wonderful! 4.8/5
                                      (11 reviews)
                                      $76
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Farmhouse #6755518
                                      11
                                        • 7 BR
                                        • 4 BA
                                        • 1 HF BA
                                        • Sleeps 17
                                        House #8131077
                                        10
                                          • 3 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 7
                                          Cottage #1880426
                                          8
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 4
                                            Cottage #8089269
                                            1 Review
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Cottage #8031311
                                              34
                                                • 5 BR
                                                • 1 BA
                                                • Sleeps 12
                                                House #8155350
                                                2 Reviews
                                                  Wonderful! 4.9/5
                                                  (12 reviews)
                                                  $95
                                                  avg/night
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 6
                                                  Cottage #8123500
                                                  12
                                                    Exceptional! 5.0/5
                                                    (6 reviews)
                                                    avg/night
                                                    • 8 BR
                                                    • 2 BA
                                                    • 3 HF BA
                                                    • Sleeps 15
                                                    Chateau / Country House #404339
                                                    6
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Cottage #6535431
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 20
                                                        Barn #6812536
                                                        2 Reviews
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          Cottage #1864775
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 3
                                                            Cottage #1862004
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Cottage #6837071
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                Cottage #1968554
                                                                  • 3 BR
                                                                  • Sleeps 6
                                                                  Cottage #1867418
                                                                    Exceptional! 5.0/5
                                                                    (20 reviews)
                                                                    $77
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Cottage #8147896
                                                                    20
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Cottage #8110904
                                                                      2 Reviews
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 3
                                                                        Cottage #6731190
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Barn #6556196
                                                                          6
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 4
                                                                            Cottage #6515309
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 5
                                                                              Multiple rentals Cottage #1019849
                                                                              6
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Cottage #1864873
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Multiple rentals Bungalow #1019849
                                                                                  3
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 9
                                                                                    House #838758
                                                                                    9
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      Multiple rentals Bungalow #1019849
                                                                                      2 Reviews
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Multiple rentals Cottage #1019849
                                                                                        2 Reviews
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 3
                                                                                          Multiple rentals Bungalow #1019849
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Cottage #6826471
                                                                                              • 3 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              Cottage #8159302
                                                                                              11
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 4
                                                                                                Barn #6559144
                                                                                                3
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 10
                                                                                                  Cottage #1868506
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Apartment #8120811
                                                                                                    17
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Cottage #1864776
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chepstow: Cottages, Barns & More (300+)

                                                                                                       

                                                                                                      Recent Chepstow Reviews

                                                                                                      Simply lovely!

                                                                                                      4 of 5
                                                                                                      We had a lovely stay in the converted barn this November. All conveniences were provided and the place was large and nicely appointed. The grounds are pretty and well-maintained. We wish we could have stayed longer. The only thing of note was the heating is via the floor and took a good bit of time to warm the place up. Our host did note that there had been an issue with the boiler shortly before our arrival so that may have been why it started out a little chilly. The thick, luxurious bedding however, made for a cozy night's sleep. :)
                                                                                                      • Submitted: Dec 6, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Very nice cottage in a great location

                                                                                                      5 of 5
                                                                                                      We wanted to explore Wales and visit a number of castles in the area and we thought this cottage would be a good location to travel from. The cottage has been updated and it was very clean and well maintained. Doug (owner) was nice enough to have eggs, butter, bread and a bottle of wine waiting for us at check in. Him and his wife were extremely friendly, helpful and easy to work with. We had dinner at The White Horse pub (down the street) and the food and service were very good. While we traveled in November (not the greatest weather in England) we were lucky as the temps were in the high 50's and the days were sunny. While the cottage is a little hard to find, we were able to travel everywhere from this location which was very convenient. We visited Pembroke Castle, Caerphilly, Cardiff Castle. Chepstow, Raglan and a few more. I'm sure that the pool and tennis courts would be nice to use if we came at a different time. I would recommend this cottage and working with Doug was a pleasure.
                                                                                                      • Submitted: Nov 21, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Very cosy cottage with everything I needed and dog friendly.

                                                                                                      4 of 5
                                                                                                      Definitely a 5 star stay- very welcoming/cosy cottage with everything I needed. Owner even thought about the dogs with dog biscuits and blankets. Had a wonderful stay and enjoyed all the information about the area and vicinity.
                                                                                                      • Submitted: Nov 14, 2016
                                                                                                      • Stayed: Oct 2016