Holiday houses in Castellina in Chianti

Casa Mirella in Chianti

Nestled among the rolling Tuscan hills, our apartment is the ideal choice for those who want to experience an authentic stay in the Chianti Classico region. The terrace offers a relaxing space where you can enjoy a glass of wine while admiring the view. The location is strategic: 28 km from Siena and 45 km from Florence, in the heart of medieval villages, among renowned wineries, farms and suggestive Etruscan tombs, to be visited by those who love history and culture. Experience the most authentic Tuscany: we look forward to seeing you!

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organising a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle, hills and vineyards with unique sunsets.

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Dream farmhouse in Chianti, with a panoramic garden

"BADIA A PASSIGNANO DWELLING" You will enjoy a relaxing and restorative holiday in the heart of the Chianti Classico region. You will stay in a fully restored, ancient stone barn with a large fenced garden and an old gazebo, suitable for large groups and families. The rooms are comfortable and spacious for 8 people. The renovation has been carried out with great care, taking into account every aesthetic detail to allow you to experience the ancient Tuscan tradition combined with comfortable modernity.

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Edera

The apartment is located in the new “CASA VACANZE SQUARCIALUPI” building, 100 meters from the historic center of Castellina in Chianti. Attention to detail, it is finely furnished in marble, with relaxing neutral and natural colors that recall the Provencal style. Very bright and spacious, it has an area of about 45 square meters and also has a loggia. On foot you can reach: restaurants, wine bars, bars, banks, laundry, supermarket, clothing stores, food stores, baker.

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Farmhouse with pool Godenano di Mezzo

Apartment located in an old renovated farmhouse just a few minutes from the center of Castellina in Chianti. Surrounded by the Tuscan hills, it offers accommodation in independent apartments finely furnished in the traditional Tuscan style. The apartment on the ground floor is equipped with all comforts and a private space outside where you can relax and eat in peace. It shares the rest of the garden, the barbecue area and the pool area with two other apartments.

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Apartment T4

On the ground floor there is a well-equipped kitchen, a living room with a fireplace (not active), a spacious dining room and a bathroom. Going up the stairs you enter the first floor, which has two double bedrooms, each with a private bathroom. The T4 apartment boasts a breathtaking view of the Chianti countryside, which can be appreciated thanks to the outdoor gazebo with barbecue.

La Querce in Rocca di Castellina

Rocca di Castellina is a small and peaceful hamlet set on a family-run agriturismo in the heart of the Chianti Classico, where wine and olive oil are produced on site. The property consists of two holiday apartments located next to the farmhouse of the friendly owner family, as well as a detached villa a short distance uphill, converted from a former barn.