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Castellina in Chianti: 81 properties found

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Book now with free cancellation and no hidden fees, stay till 31 Dec 2026.
A double bed in front of large Black Friday logo
Situated in Castellina in Chianti, 15 km from Piazza Matteotti, PODERE 1384 features accommodation with an outdoor swimming pool, free private parking, a garden and a terrace.
Managed directly by the owner, Albergo Palazzo Squarcialupi is a 15th-century building in Castellina in Chianti. It offers a garden with outdoor swimming pool, and a spa.
Podere Palazzolo is a country farmhouse set outside Castellina in Chianti. It has large gardens with swimming pool overlooking the Chianti Valley. Parking and Wi-Fi are free.
Castello di Fonterutoli Wine Resort is a medieval country village in Tuscany's Chianti wine district 5 km outside Castellina in Chianti. It offers a restaurant and wine cellar to visit.
In the heart of Tuscany’s Chianti region, Relais Riserva di Fizzano has gardens, a gourmet restaurant, and a large pool.
Hotel Colle Etrusco Salivolpi is a recently converted farmhouse in the heart of Tuscany, near Castellina in Chianti. It is surrounded by a private garden with swimming pool and free Wi-Fi.
Overlooking the Chianti hills, Agriturismo Casale Dello Sparviero is set in a former monastery. It features a panoramic garden and free Wi-Fi throughout.
Borgo di Pietrafitta Relais is situated in a delightful spot among the green Tuscan hills. Enjoy comfortable apartments between Florence 48 km away and Siena, 20 km away.
Featuring pool views, Agriturismo La Ferrozzola offers accommodation with patio, around 22 km from Piazza Matteotti.
Villa Gran Sogno in Castellina in Chianti provides adults-only accommodation with an infinity pool, a garden and a bar.
Villa Cristina is situated in Castellina in Chianti, 20 km from Piazza Matteotti, 25 km from Piazza del Campo, and 41 km from Piazzale Michelangelo.
Sustainability certification
A former 16th-century farmhouse surrounded by vineyards, Locanda Le Piazze is now a small, luxurious, boutique hotel 6 km from Castellina in Chianti.
Located 5 km from Castellina In Chianti, Querceto Di Castellina is a 14th-century building and offers an outdoor pool, garden and accommodation with a patio.
Surrounded by vineyards, Belvedere Di San Leonino is located in Castellina in Chianti, in the heart of the Chianti area.
Boasting air-conditioned accommodation with a patio, Luxury Serviced Cottage in a Historical Chianti Borgo is situated in Castellina in Chianti.
Situated just 16 km from Piazza Matteotti, Nittardi features accommodation in Castellina in Chianti with access to a garden, barbecue facilities, as well as luggage storage space.
Providing garden views, Collelungo in Castellina in Chianti provides accommodation, pool with a view, a garden, a bar, barbecue facilities and a shared lounge.
Set in the Chianti area, in the middle of the Tuscan countryside, Villa Di Capovento is an antique stone villa with outdoor pool. It is a 30-minute drive from Siena.
Offering a garden and garden view, Casa Vacanze Squarcialupi is set in Castellina in Chianti, 20 km from Piazza Matteotti and 22 km from Piazza del Campo.
Set in Castellina in Chianti in the Tuscany region and Piazza del Campo reachable within 19 km, Podere Sagna offers accommodation with free WiFi, a children's playground, a seasonal outdoor swimming...
Boasting pool views, Agriturismo Villa Godenano - Pool&Restaurant provides accommodation with pool with a view, a garden and a tennis court, around 21 km from Piazza Matteotti.
The Residenzia Del Sogno is in the heart of the Chianti region, surrounded by vineyards and gardens with barbecue facilities. It offers free parking and free Wi-Fi.
Casa Anna is located in Castellina in Chianti, 42 km from Piazzale Michelangelo, 42 km from Pitti Palace, and 42 km from Strozzi Palace.
Situated in Castellina in Chianti, in a historic building, 16 km from Piazza del Campo, Salto di Gatto is a holiday home with a garden and barbecue facilities.
Located in Castellina in Chianti, 20 km from Piazza Matteotti and 22 km from Piazza del Campo, Palazzo Bianciardi Attico provides accommodation with free WiFi in a historic building.
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