
Holiday houses in Castellina in Chianti
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Quick stats about holiday rentals in Castellina in Chianti

Total holiday rentals
Explore 70 holiday rentals in Castellina in Chianti

Nightly prices starting at
Castellina in Chianti holiday rentals start at $71 AUD per night before taxes and fees

Verified guest reviews
Over 1,400 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
60 of Castellina in Chianti holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castellina in Chianti rentals

4.7 Average rating
Castellina in Chianti stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Castellina in Chianti
Guests agree: these stays are highly rated for location, cleanliness and more.

Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience
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Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.
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Villa Padronale - IlVillinoFarmhouse
Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa
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Appartamento 1 piano con piscina condivisa - 4 pax
Benvenuti al Casale dello Sparviero, tenuta agricola a conduzione familiare di 400 ettari. Alloggerete in un antico monastero completamente immerso nel verdi colline del Chianti Classico, a soli 20 minuti da Siena. I nostri alloggi si trovano su due piani, raggiungibili da scale esterne. La piscina a sfioro è a fruizione di tutti gli ospiti dell'agriturismo (21 persone). Il nostro personale è a vostra disposizione per visite in cantina, degustazioni e quant'altro durante il vostro soggiorno.
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Cipressini 1 - Swimming pool and stunning view
Ancient stone barn adjacent to the main farmhouse dating back to the 17. century, located in the heart of the Chianti Classico on the side of a slope with breathtaking views over the Val d'Elsa. Luxuriously renovated and furnished, equipped with every comfort, it is located in such a way as to guarantee absolute privacy. On the GF: Kitchen, large living room with fireplace and double sofa bed. On the LGF: Bedroom with double bed, built-in wardrobes, desk, bathroom with shower, utility room
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Palazzo Bianciardi - Attico
Amazing penthouse in Castellina in Chianti. Palazzo Bianciardi is a historical building owned by my family since 1434. The penthouse is independent, the entrance is shared with the first floor where we live, my husband and I, with 3 crazy cats. From the windows, magnificent views of the countryside and the rooftops! Living room with kitchen, 1 bathroom with shower, 1 passing bedroom with one double and one single bed (or 3 single, if you prefer), another large bedroom with one double bed.
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Casa Mirella nel Chianti
Immerso tra le dolci colline toscane, il nostro appartamento è la scelta ideale per chi desidera vivere un soggiorno autentico nel Chianti Classico. Il terrazzo offre uno spazio rilassante dove gustare un calice di vino ammirando il panorama. La posizione è strategica: 28 km da Siena e 45 km da Firenze, nel cuore dei borghi medievali, tra cantine rinomate, aziende agricole e suggestive tombe etrusche, da visitare per chi ama storia e cultura. Vivi la Toscana più autentica: ti aspettiamo!
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Appartamento "Gardenia"
L' appartamento si trova nella nuova struttura “CASA VACANZE SQUARCIALUPI", a 100 metri dal centro storico di Castellina in Chianti. Ambiente curato nei dettagli, è finemente arredato in marmo, dai colori rilassanti neutri e naturali che richiamano lo stile provenzale. Molto luminoso e ampio ha una superficie di circa 42 mq ed è disposto su due piani . A piedi puoi raggiungere : ristoranti , enoteche, bar, banche, lavanderia, supermercato, negozi di abbigliamento, alimentari, fornaio.•
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Casa al Gianni - Il Fienile di Simignano
Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!
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Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.
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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.
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Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.
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Popular amenities for Castellina in Chianti holiday rentals
Other great holiday rentals in Castellina in Chianti

Luxury Medieval Tower • Exclusive Chianti Stay
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House in agriturismo with pool Godenano di Mezzo
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La Querce at Rocca di Castellina
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Lorenzo Charme nel Chianti
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Authentic Tuscany Experience in our Country House
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Tuscany jem: La Casa del Fattore del Chianti
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Apartment with stunning view on the vineyards
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Fienile House
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When is the best time to visit Castellina in Chianti?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $217 AUD | $213 AUD | $233 AUD | $246 AUD | $233 AUD | $250 AUD | $250 AUD | $251 AUD | $263 AUD | $241 AUD | $217 AUD | $215 AUD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Frequently Asked Questions
What are the best places to stay in Castellina in Chianti?
Stays around the historic town center or surrounding countryside are often suggested, featuring stone farmhouses, vineyard guesthouses, and apartments with scenic views. Many choices highlight local architecture and offer a peaceful setting.
What are the best things to do in Castellina in Chianti with kids?
Families can explore the medieval fortress, discover ancient tunnels like Via delle Volte, or enjoy picnics among vineyard landscapes. Seasonal festivals and local gelaterias add to the experience for children.
What are some of the best things to do in Castellina in Chianti?
Experience the Rocca di Castellina fortress, stroll the underground Via delle Volte, and sample Chianti Classico wines at local cellars. Artisanal crafts and historic churches around the town are often highlighted by explorers.
How is the weather in Castellina in Chianti?
Castellina in Chianti has mild winters around 36–55°F (2–13°C) and summers that reach 65–90°F (18–32°C), with drier months in July and August. Spring and autumn bring moderate temperatures and increased rain, so a light jacket is useful year-round.
When is the best time to visit Castellina in Chianti?
Late spring and early autumn are frequently suggested for pleasant temperatures, fewer crowds, and vibrant vineyard colors. Summer brings lively festivals and warm afternoons, while winter offers a quieter pace and mild weather.
What are the best places to visit in Castellina in Chianti?
Castellina in Chianti has the Rocca di Castellina fortress, the Archaeological Museum of the Chianti area, and the historic Via delle Volte. Strolling through the main piazza often reveals local flavor and architecture.
What are some hiking trails in Castellina in Chianti?
Castellina in Chianti has walking paths through vineyards, olive groves, and gentle hills, often linking to neighboring villages. Marked trails allow hikers to experience changing landscapes and panoramic Tuscan views.
What are some family activities we can do in Castellina in Chianti?
Families can tour the Rocca di Castellina, walk the scenic paths around local vineyards, or visit interactive exhibits at the Archaeological Museum of the Chianti area. Many enjoy gelato in the town piazza after a day of exploring.
What are some of the best day trip ideas from Castellina in Chianti?
Travelers frequently explore nearby medieval villages, visit scenic vineyards for tastings, or walk through the rolling Tuscan countryside. Cultural experiences can also include stopping by local artisans’ studios and historic churches in surrounding hill towns.
Are there any pet friendly accommodations available in Castellina in Chianti?
Several accommodations in Castellina in Chianti are designed to welcome pets, often providing outdoor spaces and easy access to walking paths. Always check property details for specific pet policies before booking.
What are some local tips for visiting Castellina in Chianti?
Greet shop owners and locals with a friendly 'buongiorno,' and consider stopping at small vineyards for intimate tastings. Early mornings are peaceful for photography, and exploring side streets often reveals artisan workshops or specialty food shops.
What is Castellina in Chianti known for?
Castellina in Chianti is known for Chianti Classico wine production, medieval architecture, and scenic landscapes dotted with vineyards and olive groves. Its rich history includes ancient Etruscan sites and a well-preserved village atmosphere.
What are the best hidden gems to explore in Castellina in Chianti?
Explore the town’s ancient underground Via delle Volte, or discover smaller art galleries displaying regional works. Family-run shops and lesser-known vineyards around Castellina in Chianti often provide a deeper glimpse into local traditions.
What are the best foods to try in Castellina in Chianti?
Local cuisine features Tuscan specialties like wild boar ragù, hand-rolled pici pasta, and pecorino cheese. The area is known for its Chianti Classico wines, as well as rustic breads and olive oil.
What should I bring for a trip to Castellina in Chianti?
Bring comfortable walking shoes, layers for changing temperatures, and a sun hat for warm days. A light rain jacket is helpful, especially in spring and autumn, and a camera is useful for recording vineyard and village scenes.
What is the nightlife in Castellina in Chianti like?
Castellina in Chianti has a relaxed nightlife scene, centered around wine bars, cozy cafes, and traditional trattorias where people gather in the evening. Visitors frequently enjoy local wines in a welcoming, convivial atmosphere.
What are the most popular events or festivals in Castellina in Chianti?
Wine festivals highlighting Chianti Classico and local food celebrations are often held in late spring and throughout the summer. Seasonal markets and cultural fairs add to the festive atmosphere in the main piazza.
Are there family friendly vacation rentals in Castellina in Chianti?
Many vacation rentals in Castellina in Chianti are designed to welcome families, providing amenities such as spacious kitchens, outdoor areas, and access to swimming pools. Guests often find options suited for multigenerational stays.
Destinations to explore
- House rentals Castellina in Chianti
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- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Mercato Centrale
- Spiagge Bianche
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden





