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Villas in Castellina in Chianti

Escape to Tuscany's hidden gem, Castellina in Chianti. Discover charming villas, rolling hills, and authentic Italian charm. Experience la dolce vita!

Villas in Castellina in Chianti

Nice apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
4.0/5
£133  night
4
2
2
Details View Offers
Large, beautiful villa in Tuscan Hills of Chianti, Stunning gardens and large po
£3308  night
18
10
9
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Casa Fioraie - Holiday Home in Castellina in Chianti, Tuscany
4.9/5
£320  night
6
2
3
Details View Offers
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
4.9/5
£1029  night
13
6
6
Details View Offers
Villa Villa "Cottage San Bartolomeo" with Mountain View, Pool & Wi-Fi"Cottage San BartolomeoVilla "Cottage San Bartolomeo" with Mountain View, Pool & Wi-Fi" with Mountain View, Pool & Wi-Fi
5.0/5
£1573  night
4
3
1
Details View Offers
Villa Beba In Castellina in Chianti, Tuscany
4.0/5
£362  night
10
5
4
Details View Offers
Comfortable villa part of an organic winery, Castellina in Chianti.
£591  night
8
4
4
Details View Offers
Villa il Cellese in Tuscany by Fantasia Villas
£7882  night
19
10
11
Details View Offers
Villa W Infinty Pool Villa in the Heart of Chianti
£478  night
10
5
4
Details View Offers
Beautiful apartment in villa with pool, WIFI, ABeautiful apartment in villa with pool, WIFI, A/C, TV, patio, panoramic view and parking/C, TV, patio, panoramic view and parking
£218  night
6
3
3
Details View Offers
Santantimo In Castellina in Chianti, Tuscany
4.7/5
£406  night
10
5
5
Details View Offers
Luxury converted barn with hilltop views in chianti wine region, Tuscany
5.0/5
£303  night
6
3
3
Details View Offers
Wonderful private villa with AWonderful private villa with A/C, WIFI, private pool, TV, veranda and parking, close to Siena/C, WIFI, private pool, TV, veranda and parking, close to Siena
£607  night
16
7
6
Details View Offers
Il Cipresso, Radda in Chianti, Siena and Chianti
5.0/5
£135  night
4
2
1
Details View Offers
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views
4.8/5
£397  night
14
7
7
Details View Offers
Yellow House Country Villa in Chianti Classico
5.0/5
£50  night
9
3
3
Details View Offers
Fioraie villa with pool and breathtaking views for 6 people
3.7/5
£219  night
6
3
3
Details View Offers
Large Villa near Panzano Tuscany
£2688  night
14
7
7
Details View Offers
Wonderful private villa with private pool, WIFI, TV, patio and parking, close to Greve In Chianti
5.0/5
£539  night
12
6
7
Details View Offers
Casetta Erika, Castellina in Chianti, Siena and Chianti
£232  night
4
3
2
Details View Offers

Why a holiday villa in Castellina in Chianti

Experience la dolce vita in one of Tuscany's most picturesque towns, Castellina in Chianti. This charming hilltop village is nestled among rolling hills, vineyards and olive groves, offering a quintessential Italian holiday experience. From the moment you step into your villa, you'll feel like you're part of this beautiful region.

Spend your days exploring the narrow streets of Castellina, discovering hidden gems like ancient churches, charming cafes and local shops selling handmade crafts and delicious food products. Visit the nearby wineries to taste some of Tuscany's famous wines and enjoy a leisurely lunch at one of the many agriturismos (farm stays). As the sun sets, return to your villa and relax in its beautiful garden or by the pool, taking in the breathtaking views of the Chianti countryside.

When to rent a villa in Castellina in Chianti

Castellina in Chianti enjoys a Mediterranean climate, with warm summers and mild winters. The best time to visit depends on your preferences, but generally, spring (April-May) and autumn (September-October) are the most pleasant seasons. During these periods, the weather is warm and sunny, with average temperatures ranging from 18-22°C (64-72°F). This is an ideal time for outdoor activities such as hiking, biking, or simply exploring the countryside.

Summer months (June-August) can get hot, especially in July and August, when temperatures often reach up to 30°C (86°F). However, this is also the peak tourist season, and you'll find more people visiting the area. If you're looking for a peaceful experience and don't mind the heat, summer might be a good time for you. On the other hand, if you prefer milder weather and smaller crowds, consider visiting in spring or autumn. Winters (December-February) are generally cool and quiet, with temperatures ranging from 5-10°C (41-50°F). This is a great time to explore the local museums, taste some of the region's excellent winter wines, or simply relax at your villa.

Where to go in Castellina in Chianti

Castellina in Chianti's surrounding countryside offers a diverse range of experiences to suit all tastes and preferences. For those seeking relaxation and tranquility, head to the nearby hills and villages such as Radda or Gaiole, where you can enjoy peaceful walks and take in the stunning views. Alternatively, visit the charming town of San Gimignano, famous for its medieval towers and delicious local cuisine.

If you're looking for a more lively experience, Castellina's historic centre is perfect for getting lost in its narrow streets, browsing local shops and enjoying a gelato or coffee at one of the many cafes. In the evening, head to the nearby town of Siena, which comes alive with a vibrant nightlife scene, offering everything from live music to bars and restaurants. For foodies, Castellina is renowned for its excellent restaurants serving traditional Tuscan cuisine, and you'll find plenty of options in the village itself or in the surrounding countryside.

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Family friendly villas
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Private pool villas
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Villas near golf course
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Villas in Castellina in Chianti

Nice apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
4.0/5
£133  night
4
2
2
Details View Offers
Large, beautiful villa in Tuscan Hills of Chianti, Stunning gardens and large po
£3308  night
18
10
9
Details View Offers
Casa Fioraie - Holiday Home in Castellina in Chianti, Tuscany
4.9/5
£320  night
6
2
3
Details View Offers
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
4.9/5
£1029  night
13
6
6
Details View Offers
Villa Villa "Cottage San Bartolomeo" with Mountain View, Pool & Wi-Fi"Cottage San BartolomeoVilla "Cottage San Bartolomeo" with Mountain View, Pool & Wi-Fi" with Mountain View, Pool & Wi-Fi
5.0/5
£1573  night
4
3
1
Details View Offers
Villa Beba In Castellina in Chianti, Tuscany
4.0/5
£362  night
10
5
4
Details View Offers
Comfortable villa part of an organic winery, Castellina in Chianti.
£591  night
8
4
4
Details View Offers
Villa il Cellese in Tuscany by Fantasia Villas
£7882  night
19
10
11
Details View Offers
Villa W Infinty Pool Villa in the Heart of Chianti
£478  night
10
5
4
Details View Offers
Beautiful apartment in villa with pool, WIFI, ABeautiful apartment in villa with pool, WIFI, A/C, TV, patio, panoramic view and parking/C, TV, patio, panoramic view and parking
£218  night
6
3
3
Details View Offers
Santantimo In Castellina in Chianti, Tuscany
4.7/5
£406  night
10
5
5
Details View Offers
Luxury converted barn with hilltop views in chianti wine region, Tuscany
5.0/5
£303  night
6
3
3
Details View Offers
Wonderful private villa with AWonderful private villa with A/C, WIFI, private pool, TV, veranda and parking, close to Siena/C, WIFI, private pool, TV, veranda and parking, close to Siena
£607  night
16
7
6
Details View Offers
Il Cipresso, Radda in Chianti, Siena and Chianti
5.0/5
£135  night
4
2
1
Details View Offers
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views
4.8/5
£397  night
14
7
7
Details View Offers
Yellow House Country Villa in Chianti Classico
5.0/5
£50  night
9
3
3
Details View Offers
Fioraie villa with pool and breathtaking views for 6 people
3.7/5
£219  night
6
3
3
Details View Offers
Large Villa near Panzano Tuscany
£2688  night
14
7
7
Details View Offers
Wonderful private villa with private pool, WIFI, TV, patio and parking, close to Greve In Chianti
5.0/5
£539  night
12
6
7
Details View Offers
Casetta Erika, Castellina in Chianti, Siena and Chianti
£232  night
4
3
2
Details View Offers