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In the heart of the chianti region of Tuscany, holiday rental accommodation in Castellina in Chianti would suit anyone seeking the ideal destination for a truly authentic experience of rural life in the beautiful province of Siena - holiday villas and apartments in Castellina in Chianti being found in situations of peaceful seclusion surrounded by the rolling hills and sun-drenched vineyards that give this area its unique and distinctive identity. Only 90 kms away from Pisa and even closer to Siena and Florence, holiday accommodation in Castellina in Chianti can let you strike the perfect balance between rustic bliss and urban excitement, particularly as you can plan a day of historical and cultural enlightenment in any one of these cities knowing that your villa or apartment rental in Castellina in Chianti will provide an atmosphere of tranquility that is guaranteed to help you relax and recover from a hectic round of shopping and sightseeing. Where holiday villas in Castellina in Chianti are a fabulous option and offer as much character and charm as some of the traditional farmhouses in Tuscany, holiday accommodation in Castellina in Chianti of any kind will appeal to anyone hoping to swop the same old stressful routine of home for a breathe of fresh air and a slice of country life in Italy.

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  • Showing 1-50 of 300+
Additional service fee may apply.
    Villa #1934854
    • 8 BR
    • 4 BA
    • Sleeps 16
    5

    Instant confirmation

    Your booking request will be confirmed immediately.

      Villa #421433
      • 3 BR
      • 3 BA
      • Sleeps 6
      20

      Confirmation within 24 hours

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

        Multiple rentals Villa #8120549
        • 4 BR
        • 2 BA
        • Sleeps 7

        Confirmation within 24 hours

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

          Farmhouse #8461
          • 3 BR
          • 3 BA
          • Sleeps 6
          9

          Confirmation within 24 hours

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

            Farmhouse #89525
            • 3 BR
            • 2 BA
            • Sleeps 6
            13

            Confirmation within 24 hours

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

              Villa #6842529
              • 8 BR
              • 7 BA
              • Sleeps 16

              Instant confirmation

              Your booking request will be confirmed immediately.

                Multiple rentals Apartment #8120549
                • 2 BR
                • 1 BA
                • Sleeps 6

                Confirmation within 24 hours

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

                  House #1216286
                  • 3 BR
                  • 3 BA
                  • Sleeps 6

                  Confirmation within 24 hours

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

                    Apartment #9457
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    4

                    Confirmation within 24 hours

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

                      Chateau / Country House #6738102
                      • 2 BR
                      • 1 BA
                      • Sleeps 6

                      Confirmation within 24 hours

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

                        Apartment #876923vb
                        • 2 BR
                        • 1 BA
                        • Sleeps 5

                        Confirmation within 24 hours

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

                          Villa #6893849
                          • 5 BR
                          • 3 BA
                          • Sleeps 15

                          Confirmation within 24 hours

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

                            Villa #6847496
                            • 2 BR
                            • 3 BA
                            • Sleeps 6

                            Instant confirmation

                            Your booking request will be confirmed immediately.

                              Apartment #6196463
                              • 2 BR
                              • 1 BA
                              • Sleeps 5
                              46

                              Confirmation within 24 hours

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

                                Farmhouse #435593vb
                                • 3 BR
                                • 3 BA
                                • Sleeps 8
                                29

                                Confirmation within 24 hours

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

                                  Farmhouse #2559183
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 4
                                  1 Review

                                  Confirmation within 24 hours

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                                    Cottage #1207142
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    11

                                    Confirmation within 24 hours

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                                      Castle #825856
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 2
                                      19

                                      Confirmation within 24 hours

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                                        Multiple rentals Apartment #8125211
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        5

                                        Confirmation within 24 hours

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

                                          Apartment #6831648
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 5

                                          Confirmation within 24 hours

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

                                            Villa #1097226
                                            • 5 BR
                                            • 5 BA
                                            • Separate Toilet
                                            • Sleeps 10
                                            4

                                            Confirmation within 24 hours

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

                                              Chateau / Country House #1890995
                                              • 4 BR
                                              • 2 BA
                                              • Separate Toilet
                                              • Sleeps 10

                                              Confirmation within 24 hours

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

                                                Villa #6865207
                                                • 10 BR
                                                • 10 BA
                                                • Sleeps 25

                                                Confirmation within 24 hours

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

                                                  Studio #6447948
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  1 Review

                                                  Confirmation within 24 hours

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

                                                    Multiple rentals Farmhouse #455240
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    10

                                                    Confirmation within 24 hours

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

                                                      Multiple rentals Apartment #8125211
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      3

                                                      Confirmation within 24 hours

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

                                                        Cottage #8088621
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 5
                                                        2 Reviews

                                                        Confirmation within 24 hours

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

                                                          Villa #6895841
                                                          • 5 BR
                                                          • 5 BA
                                                          • Sleeps 10

                                                          Confirmation within 24 hours

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

                                                            Villa #602659vb
                                                            • 4 BR
                                                            • 4 BA
                                                            • Sleeps 9
                                                            12

                                                            Confirmation within 24 hours

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

                                                              Multiple rentals Castle #638158
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 6

                                                              Confirmation within 24 hours

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

                                                                Multiple rentals Castle #638158
                                                                • 5 BR
                                                                • 4 BA
                                                                • Sleeps 12

                                                                Confirmation within 24 hours

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

                                                                  Multiple rentals Apartment #455240
                                                                  • 1 BR
                                                                  • 1 BA
                                                                  • Sleeps 2

                                                                  Confirmation within 24 hours

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

                                                                    Apartment #6789553
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 4

                                                                    Confirmation within 24 hours

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

                                                                      Cottage #1949277
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 4
                                                                      1 Review

                                                                      Confirmation within 24 hours

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

                                                                        Villa #6862286
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        15

                                                                        Confirmation within 24 hours

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

                                                                          Villa #604892vb
                                                                          • 5 BR
                                                                          • 5 BA
                                                                          • Sleeps 13

                                                                          Confirmation within 24 hours

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

                                                                            Villa #902391vb
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8

                                                                            Confirmation within 24 hours

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

                                                                              Barn #1878423
                                                                              • Studio
                                                                              • 1 BA
                                                                              • Sleeps 3
                                                                              1 Review

                                                                              Confirmation within 24 hours

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

                                                                                Apartment #435134
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                22

                                                                                Confirmation within 24 hours

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

                                                                                  Apartment #6735666
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  17

                                                                                  Confirmation within 24 hours

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

                                                                                    Apartment #1839664
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    5

                                                                                    Confirmation within 24 hours

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

                                                                                      Villa #8043542
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Separate Toilet
                                                                                      • Sleeps 7
                                                                                      2 Reviews

                                                                                      Confirmation within 24 hours

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

                                                                                        Villa #6833488
                                                                                        • 6 BR
                                                                                        • 7 BA
                                                                                        • Sleeps 12
                                                                                        3

                                                                                        Confirmation within 24 hours

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

                                                                                          Apartment #2551718
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          1 Review

                                                                                          Confirmation within 24 hours

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

                                                                                            House #413951
                                                                                            • 1 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 2
                                                                                            22

                                                                                            Confirmation within 24 hours

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

                                                                                              House #1922653
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6

                                                                                              Confirmation within 24 hours

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

                                                                                                Apartment #1148424
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                4

                                                                                                Confirmation within 24 hours

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

                                                                                                  Villa #6835857
                                                                                                  • 3 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 8
                                                                                                  2 Reviews

                                                                                                  Confirmation within 24 hours

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

                                                                                                    Apartment #4266124
                                                                                                    • 1 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 2

                                                                                                    Confirmation within 24 hours

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

                                                                                                      Farmhouse #1842956
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 8
                                                                                                      4

                                                                                                      Confirmation within 24 hours

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

                                                                                                      • 1 - 50 of 300+

                                                                                                      Holiday Accommodation Castellina in Chianti (300+)