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Castellina in Chianti: Apartments, Villas & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    Very Good! 4.0/5
    (5 reviews)
    avg/night
    • 8 BR
    • 4 BA
    • Sleeps 16
    Villa #1934854
    5
    Viewed 17 times in the last 48 hours
      Wonderful! 4.9/5
      (20 reviews)
      avg/night
      • 3 BR
      • 3 BA
      • Sleeps 6
      Villa #421433
      20
      Viewed 11 times in the last 48 hours
        Excellent! 4.6/5
        (9 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 6
        Farmhouse #8461
        9
        Viewed 23 times in the last 48 hours
          Exceptional! 5.0/5
          (12 reviews)
          avg/night
          • 4 BR
          • 2 BA
          • Sleeps 8
          Multiple rentals Farmhouse #1140076
          12
          Viewed 12 times in the last 48 hours
            Wonderful! 4.8/5
            (9 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 6
            Villa #64607vb
            9
            Viewed 18 times in the last 48 hours
              • 9 BR
              • 5 BA
              • Sleeps 18
              Multiple rentals Villa #1140076
              16
              Viewed 14 times in the last 48 hours
                Exceptional! 5.0/5
                (8 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 6
                Multiple rentals Farmhouse #1140076
                8
                Viewed 13 times in the last 48 hours
                  Wonderful! 4.9/5
                  (8 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 5
                  Multiple rentals Farmhouse #1140076
                  8
                  Viewed 13 times in the last 48 hours
                    avg/night
                    • 2 BR
                    • 1 BA
                    • Sleeps 6
                    Multiple rentals Farmhouse #6638853
                    Viewed 5 times in the last 48 hours
                      Exceptional! 5.0/5
                      (12 reviews)
                      avg/night
                      • 7 BR
                      • 4 BA
                      • Sleeps 14
                      Multiple rentals Farmhouse #1140076
                      12
                      Viewed 6 times in the last 48 hours
                        • 2 BR
                        • 2 BA
                        • Sleeps 7
                        Multiple rentals Farmhouse #6638853
                          • 2 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 6
                          Multiple rentals Farmhouse #6638853
                            • 4 BR
                            • 4 BA
                            • 1 HF BA
                            • Sleeps 8
                            Villa #1845034
                            Viewed 6 times in the last 48 hours
                              Exceptional! 5.0/5
                              (52 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              House #6235319
                              52
                              Viewed 48 times in the last 48 hours
                                Exceptional! 5.0/5
                                (13 reviews)
                                avg/night
                                • 4 BR
                                • 3 BA
                                • Sleeps 11
                                Villa #607748vb
                                13
                                Viewed 30 times in the last 48 hours
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 7
                                  Multiple rentals Villa #8120549
                                  Viewed 21 times in the last 48 hours
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Multiple rentals Farmhouse #1452175
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 6
                                      Multiple rentals Farmhouse #1452175
                                      4
                                      Viewed 5 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (10 reviews)
                                        avg/night
                                        • 6 BR
                                        • 6 BA
                                        • 1 HF BA
                                        • Sleeps 13
                                        Villa #3808832
                                        10
                                        Viewed 8 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (13 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 6
                                          Farmhouse #89525
                                          13
                                          Viewed 10 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (9 reviews)
                                            avg/night
                                            • 4 BR
                                            • 3 BA
                                            • Sleeps 8
                                            Villa #6345041
                                            9
                                            Viewed 19 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (12 reviews)
                                              avg/night
                                              • 6 BR
                                              • 5 BA
                                              • 1 HF BA
                                              • Sleeps 18
                                              Farmhouse #391835vb
                                              12
                                              Viewed 11 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (43 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                House #282678vb
                                                43
                                                Viewed 11 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (72 reviews)
                                                  $72
                                                  avg/night
                                                  • 2 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 5
                                                  Multiple rentals Cottage #6029171
                                                  72
                                                  Viewed 81 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (60 reviews)
                                                    $59
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Multiple rentals Apartment #6029171
                                                    60
                                                    Viewed 81 times in the last 48 hours
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Apartment #773208vb
                                                      2
                                                      Viewed 6 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (14 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        Farmhouse #654067vb
                                                        14
                                                        Viewed 13 times in the last 48 hours
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Apartment #771909vb
                                                          Viewed 6 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (16 reviews)
                                                            avg/night
                                                            • 13 BR
                                                            • 12 BA
                                                            • Sleeps 32
                                                            Villa #625123vb
                                                            16
                                                            Viewed 73 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (36 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 10
                                                              Villa #1137514
                                                              36
                                                              Viewed 47 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (36 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                House #20670
                                                                36
                                                                Viewed 27 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (9 reviews)
                                                                  $98
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 8
                                                                  Castle #1618965
                                                                  9
                                                                  Viewed 17 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (22 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    Multiple rentals Apartment #809657
                                                                    22
                                                                    Viewed 37 times in the last 48 hours
                                                                      Wonderful! 4.8/5
                                                                      (9 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 3 BA
                                                                      • Sleeps 11
                                                                      Castle #445224
                                                                      9
                                                                      Viewed 55 times in the last 48 hours
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        Cottage #1097580
                                                                        3
                                                                        Viewed 29 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (13 reviews)
                                                                          $85
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Apartment #13190
                                                                          13
                                                                          Viewed 54 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 5
                                                                            Apartment #2221635
                                                                            Viewed 8 times in the last 48 hours
                                                                              $69
                                                                              avg/night
                                                                              • Studio
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Apartment #6830964
                                                                              2
                                                                              Viewed 5 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (11 reviews)
                                                                                $98
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Cottage #1207142
                                                                                11
                                                                                Viewed 15 times in the last 48 hours
                                                                                  Wonderful! 4.9/5
                                                                                  (28 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 4 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 11
                                                                                  Chateau / Country House #1687872
                                                                                  28
                                                                                  Viewed 20 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (26 reviews)
                                                                                    $81
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 5
                                                                                    Apartment #8023809
                                                                                    26
                                                                                    Viewed 10 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (19 reviews)
                                                                                      $90
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 2
                                                                                      Castle #825856
                                                                                      19
                                                                                      Viewed 22 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (12 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #1017337
                                                                                        12
                                                                                        Viewed 15 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (5 reviews)
                                                                                          $60
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Multiple rentals Apartment #8125211
                                                                                          5
                                                                                          Viewed 13 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (8 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 2
                                                                                            Castle #3878711
                                                                                            8
                                                                                            Viewed 15 times in the last 48 hours
                                                                                              • 11 BR
                                                                                              • 9 BA
                                                                                              • Sleeps 22
                                                                                              House #2343152
                                                                                                Wonderful! 4.9/5
                                                                                                (22 reviews)
                                                                                                $54
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 3
                                                                                                Apartment #1803159
                                                                                                22
                                                                                                Viewed 30 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (14 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5
                                                                                                  Apartment #1835979
                                                                                                  14
                                                                                                  Viewed 19 times in the last 48 hours
                                                                                                    $98
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 5
                                                                                                    Apartment #6831648
                                                                                                    Viewed 26 times in the last 48 hours
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Castellina in Chianti Reviews

                                                                                                    Fantastico!

                                                                                                    5 of 5
                                                                                                    We had such a wonderful stay at the farmhouse! We (my husband, 10 year old son and I) visited at the end of November 2016 for 4 nights. Daniele and family could not have been more welcoming or accommodating. The farmhouse was cozy and quiet, and we had all the comforts of home. The views from the veranda were spectacular and the property was every bit as picturesque as it appears in the online photos. The wifi and cable signals (for those who need it) were also great. This is a great location for anyone looking for accommodations near Siena (I think it was about a 20 min drive) that would like to be out of town in a more private setting. My son was also a huge fan of the daily visits from the two local kitties, who were very sweet and friendly. Grazie Daniele e famiglia per una meravigliosa visita in Chianti!
                                                                                                    • Submitted: Dec 6, 2016
                                                                                                    • Stayed: Nov 2016

                                                                                                    Quattro Torra - Rocambolesco

                                                                                                    5 of 5
                                                                                                    Our stay in the Castello delle quattro torri, was absolutely amazing; a "rocambolesco" experience! We were met at the door by Nicola on our first day. From the moment we waited for him before entering the castle doors, it felt like we were traveling back in time. The castle is incredibly beautiful. We arrived here later in the afternoon during the magic hour of the sun; the sun was shining on the castle, the colors of the leaves were changing on the vines of the castle walls. It was just stunning. Nicola welcomed us into his family's home as if we were old family and friends. Nicola couldn't have been more helpful and attentive to our every needs. He showed us the best place to park our rental car in Sienna, which was a five minute drive (literally - no more than four or five min) to Sienna. It's a family run business. The adorable woman (I think it was his Aunt) cooking us breakfast in the mornings was so sweet and the breakfast she made us was wonderful and authentic Italian (including cappuccinos!) The rooms were immaculate and beautifully decorated. The tower room we stayed in for one night had a neat spiral staircase leading up into the sleeping area. The view from the castle (bedrooms, living room, dining area) is amazing. You can see the Tuscan hills for miles. The land around the castle is so picturesque and you are encouraged to walk this entire area, walking through the olive groves and walking through the vineyards. It feels like you are in the scene of a movie. Nicola's family owns a farm nearby the castle with a restaurant on the property called Le Pietre Vive restaurant. One of the nights, we had the most "cena deliziosa" delicious dinner. Mauro, our waiter at the restaurant was super helpful with the menu, gave the best recommendations and even shared grappa with us! Nicola also makes his own chianti wine, saffron, honey and oil. We purchased wine and honey from Nicola to take back home with us. Nicola noticed it was my husband's birthday, while we were checking in, and the next morning, on his birthday, he greeted my husband with an Italian happy birthday and so did his Aunt. We absolutely loved our stay here at Castello delle Quattro Torra and would recommend it to everyone. Sienna is an incredible little city and the quick drive from there also makes it so wonderful. Thank you so much, Nicola! Grazie Mille! Love, Nicola & Tanya
                                                                                                    • Submitted: Dec 3, 2016
                                                                                                    • Stayed: Oct 2016

                                                                                                    Meet your new Italian family

                                                                                                    5 of 5
                                                                                                    At first glance of the reviews, this b&b seemed to good to be true. It definitely lived up to all the hype and much, much more. Andrea and Lucia are incredibly sweet, kind and wonderfully caring and attentive hosts. Their home is so beautiful and has some of the most amazing views in Tuscany. It makes the drive there worth it. When driving to their home, you'll notice the amazing Tuscan views of the olive trees and vineyards in a 360 view. Upon reaching the mailboxes on the road to their home in Tavarnelle, you'll most likely be greeted by Andrea who paitiently waits with excitement for his guests to arrive or looking for his adorable dogs Pascha and Luna. They are just perfect. We loved that you immediately feel immersed in italian culture in this area. Their home is wonderful; you hear the roosters in the morning from your second floor room window. The room is perfectly sized, beautifully decorated and very cozy. The bathroom is better than a five star hotel. The dinner they cooked for us was incredible and we were given a perfect Italian breakfast each morning. We had no issues communicating with them, even considering that we don't speak Italian. Their home is nearby other smaller towns and any winery you'd want to visit (we recommend Poggio al Bosco family owned). Bottom line, this is the best VRBO we have ever stayed in and we would recommend it to everyone. We loved meeting and getting to know you both, Andrea and Lucia. We hope to see you soon again!
                                                                                                    • Submitted: Nov 10, 2016
                                                                                                    • Stayed: Oct 2016