Vacation rentals in Chiusdino

Montestigliano - Donati Villa

This traditional yet refined Italian hamlet dating back to 1783 is totally immersed in nature. Montestigliano offers its guests luxury and comfort in the heart of Tuscany, complete with all services, including a vegetable garden for guests and two swimming pools. This oasis of peace and beauty lies just 12km from Siena and a short drive away from the region’s much loved treasures such as Florence, San Gimignano, Cortona, Montepulciano and Pienza. The beautiful family-run farm sits atop its own hill, overlooking the Merse river valley. The estate is spread over two thousand acres of land covering fairy tale woodlands, fantastic cypress avenues, holm oak and cork oak trees, fields of wheat, barley, sunflowers and maze, and groves of 3,000 olive trees from which a delicious DOP extra virgin olive oil is made. Each farmhouse has been renovated in great detail, the style, décor and charm of Montestigliano make it a special and unique destination for a wonderful, enjoyable and most importantly memorable holiday. The farm offers traditional Tuscan cooking classes and olive oil tastings, starlit dinners, pizza feasts and in-house private catering or massage services. While the surrounding area presents numerous opportunities to go on peaceful strolls in nature, taste typical dishes at local restaurants, go horse riding or on bicycle tours, visit a local market, relax in a hot spring or take an afternoon dip in the nearby river. Or you can enjoy a day trip to the seaside ending with a plate of delicious fresh fish, and of course, let’s not forget the region’s multitude of local wineries offering an exquisite array of wines from both the areas of Chianti and Val d’Orcia, to be samples alongside a platter of local cheeses and cold cuts. This large typical Tuscan villa, or Fattoria as it is known in Italian, sleeps up to 14 guests (approx. 320sq m). Originally the main house on the estate, it was built in the 18th century by the well-known Roman noble Aldobrandini family, who purchased the land from the Abbey of Torri (a beautiful abbey located in a small medieval village 2km from Montestigliano and well-worth a visit). With its generous proportions and fine architectural features the house still emits a sense of nobility and is furnished with numerous elegant pieces of antique furniture and decorations. It is located across from the charming old church, a few metres from the main square and swimming pools. On the ground floor there is a large entrance hall (leading to the back garden), ground-floor lounge, fully-equipped kitchen with large traditional open fireplace and dining table, bathroom with shower, 1 triple and 1 single bedroom. A stone staircase leads to a bathroom with shower and a half landing with a twin bedroom. The first floor opens into a large living room/reception space with fireplace, 1 large bathroom with shower, 2 double bedrooms (with wash basins) and 2 twin bedrooms. Another flight of stairs leads to a half bathroom and bathroom with bathtub. The backdoor opens onto an ample open garden filled with fruit trees and vines and glorious views of the surrounding woodlands, the vine-covered stone table is the perfect spot for alfresco breakfasts to get the day started or sunset dinners with a delicious glass of local wine to help you wind down after exploring the local area. The ideal holiday home for family reunions or a gathering of friends.

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property nestled in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your heart. We look forward to welcoming you!

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

La Pergola: sunny & charming hilltop country house

In the heart of Tuscany you find the estate Tirisondola. Located on the private top of a panoramic hill near the medieval town Chiusdino, it offers uninterrupted views over Tuscan forests, hills & olive groves. Relaxing environment, with the spirit of art & history, and ideally situated near the great cultural Tuscan centers and the sea. La Pergola is one of 3 individual and lovely Tuscan country houses, fully equipped with kitchen/living room, 2 bed rooms, bath room, galleries and terrace.

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Typical Tuscan Cottage with swimming pool and park

The Country Cottage is located in the heart of authentic Tuscany, in an unspoiled area, with a unique biodiversity. Located just a 5-minute drive from the famous Abbey of San Galgano and the Hermitage of Montesiepi, where the prestigious "Sword in the Stone" is kept. The entire property is rented: the typical Tuscan country house, the swimming pool, the garden and the fenced park. A perfect location to relax with maximum privacy, without the stress and wear and tear of modern life

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

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.

Green Dome @ The Land Before Time Retreats

Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Castagnoli Apartment

Castagnoli apartment is located on the first floor of the Collepetrucci agriturismo and consists of a kitchen, a double bedroom, bedroom with two single beds, bathroom, and external veranda. The apartment is independent, fully equipped, and the entire apartment is rented. The use of the swimming pool is shared.

Apartment in Old Farmhouse

My accommodation is close to the city center, panoramic views, art and culture, restaurants and parks. My accommodation is suitable for couples, lone adventurers, families and to all lovers of beauty. Air conditioning is installed in the main room, and professional fans are installed in the other rooms.

Open-space rural house in San Galgano

The stylishly restored open space house has a large garden with an orchard and a vine arbor with barbecue and a spectacular view of the valley. Located in a village in the Municipality of Chiusdino near the Abbey of San Galgano.