Tuscany Siena Castellina in Chianti

Accommodation in Castellina in Chianti

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Castellina in Chianti is one of the top destinations for anyone wishing to stay in Chianti near Siena. The small city center, part of the Chianti Classico wine region, is surrounded by vineyards and wine producing estates that also offer accommodation. The city center itself is small but with lots of small shops and restaurants that serve the needs of local residents and visitors alike.

70 Properties Found: All Accommodations in Castellina in Chianti


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Il Cellese

Apartments in Chianti Farmhouse with Pool Near Siena

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  • apartments: 7
  • sleeps: 25
  • Location: Castellina in Chianti (Countryside)
  • weekly price: from € 400 to € 2100

Located in Castellina in Chianti, in the heart of Chianti area, this typical Tuscan farmhouse offers 7 independent apartments and a gorgeous villa, a large salt water pool with view on the surrounding hills and restaurant.

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Borgo Di Pietrafitta Relais

Rental Apartments in a Relais setting in Castellina in Chianti

  • apartments: 15
  • rooms: 8
  • Location: Castellina in Chianti (Countryside)
  • daily price: from € 110 to € 307

Located between Florence and Siena, in the heart of Tuscany the Borgo Pietrafitta Relais is a mix of vacation apartments and B&B where you find a panoramic pool, lush garden areas, relaxing décor and genuine Tuscan hospitality.

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La Rocca di Cispiano

Chianti Farmhouse with Apartments and Swimming Pool

  • apartments: 7
  • sleeps: 30
  • Location: Castellina in Chianti (Countryside)
  • daily price: from € 120 to € 250
  • weekly price: from € 250 to € 1045

The heart of this Chianti farmhouse is an ancient hamlet with several houses made of stone. After careful restoration, the houses have been converted into six comfortable apartments that offer guests all modern amenities that share an outdoor pool.

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Borgo Sicelle

Panoramic Chianti Family Vacation Rental Apartments

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  • apartments: 10
  • sleeps: 33
  • Location: Castellina in Chianti (Countryside)
  • daily price: from € 70 to € 195

10 self catering vacation rental apartments for families with children, couples & groups in Castellina in Chianti. Positioned on a panoramic hillside it offers picture perfect vistas of Chianti and Tuscany, only a short distance from Siena & Florence.

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Podere Patrignone

Tranquility & Chianti Charm at an Eco-Friendly Tuscany Villa

  • apartments: 6
  • rooms: 15
  • sleeps: 32
  • Location: Castellina in Chianti (Countryside)
  • daily price: from € 115 0

The ambiance at this farmhouse brings together family & friends, nature & relax. The villa rental & self catering apartments provide an ideal base for exploring Tuscany in its natural state: hiking, swimming, dinner banquets & small town adventures.

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Agriturismo Rocca

Farmhouse close to Castellina in Chianti, Siena

  • apartments: 3
  • rooms: 9
  • sleeps: 20
  • Location: Castellina in Chianti (Countryside)
  • daily price: € 80

In the heart of Chianti, a few minutes from Castellina in Chianti, 2 family managed apartments and an independent villa to offer you a welcoming stay and a wonderful holiday. Panoramic pool and wine tastings produced by the family farm!

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Romitorio di Serelle

Relaxing Tuscany Farmhouse Apartments in Chianti

  • apartments: 15
  • sleeps: 68
  • Location: Barberino Val d'Elsa (Countryside)
  • weekly price: from € 700 to € 2050

The farmhouse is located in the heart of Chianti and offers 15 apartments furnished in traditional Tuscan style and provided with all of the main services and comforts. Large swimming pool and restaurant at guests' disposal.

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Agriturismo Vernianello

Farmhouse with pool and restaurant in the Chianti Countryside

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  • apartments: 4
  • sleeps: 14
  • Location: Poggibonsi (Countryside)
  • weekly price: from € 545 to € 959

The family managed farmhouse is located in the Chianti countryside a few kilometers from San Gimignano and Siena. It has 4 comfortable apartments, a beautiful pool overlooking the surrounding hills and a restaurant serving traditional Tuscan cuisine.

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Palazzo Malaspina

Charming B&B in a small Chianti Town Between Florence and Siena

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  • rooms: 5
  • sleeps: 10
  • Location: Tavarnelle Val di Pesa (Countryside)
  • daily price: from € 80 to € 115

Elegant bed and breakfast in Chianti, located halfway between Florence and Siena. The B&B offers 5 comfortable double rooms, finely furnished and overlooking Chianti hills.

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Villa Vianci

A luxurious Villa in Chianti near Siena

  • rooms: 6
  • sleeps: 12
  • Location: Poggibonsi (Countryside)

Villa Vianci is a family run luxury rental between the hills of Chianti and the historic city of Siena. There is a beautiful green garden with pool, lots of family space throughout the villa for up to 12 PAX on holiday in Tuscany

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Borgo Scopeto Relais

Luxury resort in medieval hamlet minutes from Siena

  • apartments: 5
  • rooms: 58
  • sleeps: 150
  • Location: Siena (Countryside)
  • daily price: from € 190 to € 700

This luxury relais, set in a 13th century village, has been carefully restored and turned into elegant, modern lodgings. Surrounded by olive groves and vineyards, with breathtaking views of Siena, it also has a spa, fitness center, restaurant and pools.

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Villa Fillinelle

Luxury Accommodations near Florence: B&B or Vacation Villa

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  • apartments: 1
  • rooms: 3
  • sleeps: 12
  • Location: Tavarnelle Val di Pesa (Countryside)
  • daily price: from € 180 to € 280
  • weekly price: from € 0 6000

Lush gardens, charming decors & panoramic views. This prestigious medieval Villa has been totally restored for your holiday near Chianti & Florence. It offers two perfect solutions: 4 charming B&B rooms or the entire villa for a deluxe holiday.

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Viticcio

Cozy Farmhouse in Chianti near Greve in Chianti

  • apartments: 8
  • sleeps: 40
  • Location: Greve in Chianti (Countryside)
  • weekly price: from € 850 to € 1290

Viticcio vacation apartments are immersed in 30 hectares of splendid vineyards near Greve in Chianti, located half way between Florence and Siena. Featuring cozy apartments, WiFi, AC and a saltwater pool.

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Borgo Argenina

B&B and Private Villas in Gaiole in Chianti

  • sleeps: 22
  • Location: Gaiole in Chianti (Countryside)
  • daily price: from € 160 to € 420

A romantic & enchanting way to discover the mysteries of Tuscany at Borgo Argenina, where the B&B and private villas combine the savour perfumes from the kitchen, and the warm hospitality of your hostess for a memorable holiday adventure.

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B&B del Giglio

Finely Restored B&B in San Donato in Poggio, Chianti

  • apartments: 1
  • rooms: 2
  • sleeps: 4
  • Location: Tavarnelle Val di Pesa (City)
  • daily price: from € 80 to € 100
  • weekly price: from € 840 to € 945

Located in a lovely Chianti village, the B&B offers a charming apartment with 2 rooms, which can also be rented separately. Each room has ensuite bathroom and a great view over the surrounding countryside. A delicious breakfast is served in the morning.

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More about Castellina

Most of Castellina had to be rebuilt after World War II, but the town maintains its charm and several distinguishing characteristics such as Via delle Volte, an underground tunnel built within the defensive walls. From within, guards could observe the surrounding countryside for the approach of uninvited guests. Today, you can walk down the tunnel with its small shops and also observe the same enchanting views - but without the worry of approaching enemies!

How to get there

The town and area is easily reached by car by either following the Via Chiantigiana or "Chianti road" from either Florence or Siena or by exiting at Monteriggioni or Poggibonsi off the Florence-Siena road and following signs to Castellina. The best way to get to Castellina is to drive there; it is unfortunately poorly served by public transportation. The closest train station is called "Castellina Scalo", about 11km from Castellina in Chianti. If you're staying in the countryside, a car is definitely recommended and will make moving around Chianti and its vineyards and wineries very practical.

An interesting shop...

The Enoteca Antiquaria, located in the stately Palazzo Squarcialupi in the center of Castellina in Chianti, is an important wine shop in the entire Chianti region. The wine shop's collection includes Chianti wine from the last 100+ years, thus becoming an important historical archive of Chianti Classico wine itself.

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Florence & Tuscany tours

Florence Lucca Pisa Siena Arezzo Grosseto Livorno Pistoia Montecatini Terme San Gimignano Cortona Montepulciano Volterra Casentino Chianti Garfagnana Lunigiana Maremma Mugello Val d'Orcia Versilia Elba Island Etruscan Coast Crete Senesi Argentario