HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit

Holidaymakers searching for holiday rentals in Castellina in Chianti also enquired about apartments in San Gimignano, villas in Gaiole in Chianti and villas in Castelnuovo Berardenga

Make a holiday home, farm house or villa in Castellina in Chianti, Italy your home away from home

The idyllic little township of Castellina in Chianti is situated in the province of Siena, in the famous wine-producing region of Tuscany, Italy. Many of the picture postcard rural homes here have been converted into luxury holiday accommodation, really increasing the popularity of the area. The fact that the beautiful city of Florence is just 22 miles to the north makes Castellina in Chianti an even more appealing holiday destination, especially for couples and friends.

Things to do on holiday in Castellina in Chianti, Italy

Castellina in Chianti is the atypical image of Italy’s scenic Tuscany region – historic buildings and churches, rolling green hills and countryside, and of course vineyards where all the tasty Chianti wines are produced! Far from being just a small rural ‘comune’, Castellina in Chianti actually has a number of interesting sights to see. Dating back hundreds of years, the township was first inhabited by Etruscans and Romans, though it took on most of its current character during the 14th and 15th centuries when it was fortified. Today you can still visit the large Rocca (castle) and its 14th century tower, plus the small Etruscan museum here. When the town was fortified underground passageways were also built, such as the Via delle Volte which you can visit.

The Church of San Salvatore is another popular attraction. This was constructed in the 15th century and features a fresco from that period of the Madonna with Child. Other picturesque churches can be found in the small villages surrounding the town, as well as evidence of Castellina in Chianti’s earlier history, such as the Etruscan tomb which dates back to the 6th century. Of course one of the big attractions with this region of Italy is the vineyards, where tours and wine tasting are popular.

Places to visit on holiday in Castellina in Chianti, Italy

As if the beautiful surroundings of Castellina in Chianti weren’t enough, holiday makers renting a holiday home here can also benefit from the fact that Florence is easily accessible. Just over 20 miles away, Florence would make an ideal day trip, especially to its UNESCO World Heritage Site listed historic centre.

The city of Siena is even closer, at just 9 miles distant, and this too is listed as a UNESCO World Heritage Site. The architecture here is quite stunning!

The weather in Castellina in Chianti, Italy

Castellina in Chianti is best described as having a Mediterranean climate with hot and somewhat humid summers, with some rainfall. Winters are mild, though the region experiences a little more rainfall during this time. Find some holiday accommodation in Castellina in Chianti which has a swimming pool as this will be great for taking a dip to cool off from the summertime average high temperatures in the low 30’s C!

Flights to Castellina in Chianti, Italy

To reach your Castellina in Chianti holiday home you have several options for flights. The nearest major airport is at Florence, however, Pisa has a much better choice of airlines flying there from the UK that you can choose from. This includes budget airlines such as easyJet, Ryanair and Thomsonfly, as well as some of the world’s major airlines too.

  • Showing 1-50 of 300+
Additional service fee may apply.
    Wonderful! 4.9/5
    (21 reviews)
    avg/night
    • 3 BR
    • 3 BA
    • Sleeps 6
    Villa #421433
    21
    Viewed 58 times in the last 48 hours
      Exceptional! 5.0/5
      (60 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 4
      Multiple rentals Apartment #6029171
      60
      Viewed 179 times in the last 48 hours
        Exceptional! 5.0/5
        (72 reviews)
        avg/night
        • 2 BR
        • 3 BA
        • Separate Toilet
        • Sleeps 5
        Multiple rentals Cottage #6029171
        72
        Viewed 281 times in the last 48 hours
          Excellent! 4.6/5
          (9 reviews)
          avg/night
          • 3 BR
          • 3 BA
          • Sleeps 6
          Farmhouse #8461
          9
          Viewed 31 times in the last 48 hours
            Wonderful! 4.8/5
            (9 reviews)
            avg/night
            • 4 BR
            • 3 BA
            • Separate Toilet
            • Sleeps 6
            Villa #64607vb
            9
            Viewed 28 times in the last 48 hours
              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
                Exceptional! 5.0/5
                (12 reviews)
                avg/night
                • 7 BR
                • 4 BA
                • Sleeps 14
                Multiple rentals Farmhouse #1140076
                12
                Viewed 15 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 16 times in the last 48 hours
                    • 9 BR
                    • 5 BA
                    • Sleeps 18
                    Multiple rentals Villa #1140076
                    16
                    Viewed 38 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 37 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 8 times in the last 48 hours
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                          Multiple rentals Farmhouse #6638853
                          0
                          Viewed 8 times in the last 48 hours
                            • 4 BR
                            • 4 BA
                            • Separate Toilet
                            • Sleeps 8
                            Villa #1845034
                            0
                            Viewed 5 times in the last 48 hours
                              • 2 BR
                              • 2 BA
                              • Sleeps 7
                              Multiple rentals Farmhouse #6638853
                              0
                                Wonderful! 4.9/5
                                (9 reviews)
                                avg/night
                                • 4 BR
                                • 4 BA
                                • Separate Toilet
                                • Sleeps 8
                                Farmhouse #13754
                                9
                                Viewed 14 times in the last 48 hours
                                  • 2 BR
                                  • 2 BA
                                  • Separate Toilet
                                  • Sleeps 6
                                  Multiple rentals Farmhouse #6638853
                                  0
                                    Exceptional! 5.0/5
                                    (53 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    House #6235319
                                    53
                                    Viewed 83 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (13 reviews)
                                      avg/night
                                      • 4 BR
                                      • 3 BA
                                      • Sleeps 11
                                      Villa #607748vb
                                      13
                                      Viewed 49 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (12 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Multiple rentals Farmhouse #53674
                                        12
                                        Viewed 48 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (12 reviews)
                                          avg/night
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 9
                                          Multiple rentals Farmhouse #53674
                                          12
                                          Viewed 26 times in the last 48 hours
                                            Exceptional! 5.0/5
                                            (43 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 4
                                            House #282678vb
                                            43
                                            Viewed 44 times in the last 48 hours
                                              Excellent! 4.7/5
                                              (13 reviews)
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Farmhouse #89525
                                              13
                                              Viewed 60 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (13 reviews)
                                                avg/night
                                                • 6 BR
                                                • 5 BA
                                                • Separate Toilet
                                                • Sleeps 18
                                                Farmhouse #391835vb
                                                13
                                                Viewed 30 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (10 reviews)
                                                  avg/night
                                                  • 6 BR
                                                  • 6 BA
                                                  • Separate Toilet
                                                  • Sleeps 13
                                                  Villa #3808832
                                                  10
                                                  Viewed 33 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (9 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    Villa #6345041
                                                    9
                                                    Viewed 18 times in the last 48 hours
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 7
                                                      Multiple rentals Villa #8120549
                                                      1
                                                      Viewed 52 times in the last 48 hours
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        Multiple rentals Apartment #8120549
                                                        0
                                                        Viewed 10 times in the last 48 hours
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 4
                                                          Villa #773192vb
                                                          0
                                                          Viewed 16 times in the last 48 hours
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Apartment #771909vb
                                                            0
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Apartment #773208vb
                                                              2
                                                                Exceptional! 5.0/5
                                                                (8 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 5
                                                                Chateau / Country House #864792
                                                                8
                                                                Viewed 12 times in the last 48 hours
                                                                  • 8 BR
                                                                  • 7 BA
                                                                  • Sleeps 16
                                                                  Villa #6842529
                                                                  0
                                                                  Viewed 51 times in the last 48 hours
                                                                    • 2 BR
                                                                    • 3 BA
                                                                    • Sleeps 6
                                                                    Villa #6847496
                                                                    0
                                                                    Viewed 7 times in the last 48 hours
                                                                      Excellent! 4.6/5
                                                                      (8 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 7
                                                                      Chateau / Country House #1851746
                                                                      8
                                                                      Viewed 49 times in the last 48 hours
                                                                        • 6 BR
                                                                        • 5 BA
                                                                        • Sleeps 11
                                                                        Villa #1984292
                                                                        0
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 6
                                                                          House #1216286
                                                                          0
                                                                          Viewed 9 times in the last 48 hours
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 2
                                                                            Apartment #6482654
                                                                            3
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 2 BA
                                                                              • Sleeps 4
                                                                              Apartment #771890vb
                                                                              0
                                                                              Viewed 9 times in the last 48 hours
                                                                                Excellent! 4.6/5
                                                                                (15 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                Multiple rentals Cottage #6219947
                                                                                15
                                                                                Viewed 31 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (26 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Apartment #6273570
                                                                                  26
                                                                                  Viewed 11 times in the last 48 hours
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    Chateau / Country House #378532vb
                                                                                    1
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 4
                                                                                      Multiple rentals Apartment #6219947
                                                                                      1
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Apartment #6561871
                                                                                        0
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 5
                                                                                          Apartment #876923vb
                                                                                          0
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 5
                                                                                            Multiple rentals Mill #500232
                                                                                            4
                                                                                            Viewed 5 times in the last 48 hours
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 4
                                                                                              Multiple rentals Mill #500232
                                                                                              3
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 7
                                                                                                Villa #6482553
                                                                                                1
                                                                                                Viewed 26 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 4
                                                                                                  Apartment #2310613
                                                                                                  0
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 8
                                                                                                    House #2475519
                                                                                                    0
                                                                                                    Viewed 27 times in the last 48 hours
                                                                                                    • 1 - 50 of 300+

                                                                                                    Castellina In Chianti Holiday Apartments & Villas (300+)

                                                                                                     

                                                                                                    Recent Reviews

                                                                                                    lovely Tuscan villa, friendly staff on site

                                                                                                    5 of 5
                                                                                                    Our stay in Castellina In Chianti at your villa at the end of October was awesome. Certainly 5 out of 5 starts; beautiful grounds and view; 5-10 minute drive to Castellina In Chianti, which is a perfect, charming little town; clean, comfortable and well-appointed; friendly and helpful staff on site. I would definitely stay at this villa if I am lucky enough to visit Tuscany again, and I will certainly recommend it to my friends.
                                                                                                    • Review Submitted: 27-Dec-2016
                                                                                                    • Date of Stay: Oct 2016

                                                                                                    UNFORGETTABLE!

                                                                                                    5 of 5
                                                                                                    This was a trip of a lifetime. The spectacular views, the rustic Barn, the food, the wine, the people, and of course Serena made it unforgettable. We hope to make the visit to Tuscany and The Barn a new Thanksgiving tradition. The property was exactly as described on the website and viewed in the pictures. It was very clean and well maintained. The house had everything you needed from pots and pans to umbrellas, espresso maker, tea kettle, spices even sporting equipment. There's even thyme and rosemary growing around the property. I highly recommend this property to anyone looking to make unforgettable memories with friends and family. Oh, one more plus, each bedroom has its own bathroom!
                                                                                                    • Review Submitted: 28-Nov-2016
                                                                                                    • Date of Stay: Nov 2016

                                                                                                    Wonderful villa in a beautiful setting

                                                                                                    4 of 5
                                                                                                    This is a beautiful villa, beautifully situated on a mountaintop with wonderful views of the Chianti region from every window of the villa. The villa works great for a multi-generational get-together, as it is divided into 3 separate apartments. The grounds of the villa are gorgeous and well-kept and the pool is well-maintained. A car is necessary for any outings, as the villa is quite remote and only accessed by dirt roads. There are no restaurants, shopping or other amenities within walking distance, so a vehicle is necessary to enjoy the wonderful Chianti area. We only have good things to say about the housekeeper/keyholder, who assisted us in many aspects. All in all the villa lived fully up to our expectations and more.
                                                                                                    • Review Submitted: 13-Oct-2016
                                                                                                    • Date of Stay: Sep 2016