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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 $70 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.

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Top Guest favourite
Apartment in Asciano
4.9 out of 5 average rating, 20 reviews

Incredible Views & Pool in the Tuscan Hills

Fuggite nel cuore della Toscana e vivete un soggiorno immersi in dolci colline, una bellezza senza tempo e panorami indimenticabili. La casa offre l'accesso a una splendida piscina in comune e a tranquilli spazi esterni, perfetti per rilassarsi al sole o godersi serate serene. All'interno, troverete comfort, stile, tutto il necessario per un soggiorno memorabile. Ideale per coppie, famiglie o gruppi di amici che desiderano vivere un'autentica esperienza toscana a breve distanza in auto da Siena.

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5.0 out of 5 average rating, 345 reviews

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.

Guest favourite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti
4.93 out of 5 average rating, 254 reviews

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

Top Guest favourite
Apartment in Castellina in Chianti
4.95 out of 5 average rating, 56 reviews

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!

Top Guest favourite
A scenic balcony features a small table, adorned with bottles of wine and a dish of fresh green grapes. The view showcases rolling hills and vineyards under a clear blue sky, emphasizing the tranquil surroundings.
Apartment in Castellina in Chianti
5.0 out of 5 average rating, 29 reviews

Edera

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 45 mq dispone anche di un loggiato. A piedi puoi raggiungere : ristoranti , enoteche, bar, banche, lavanderia, supermercato, negozi di abbigliamento, alimentari, fornaio.

Top Guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.99 out of 5 average rating, 135 reviews

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.

Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 285 reviews

Casa al Gianni - Capanna

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Guest favourite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Guest favourite
A spacious swimming pool is surrounded by manicured grass. Several lounge chairs are arranged neatly along the poolside, facing the expansive view of the Tuscan hills in the background, featuring gentle slopes and a clear blue sky.
Condo in Castellina in Chianti
4.88 out of 5 average rating, 95 reviews

House in agriturismo with pool Godenano di Mezzo

Apartment located in an old renovated farmhouse just a few minutes from the center of Castellina in Chianti. Surrounded by the Tuscan hills, it offers accommodation in independent apartments finely furnished in the traditional Tuscan style. The apartment on the ground floor is equipped with all comforts and a private space outside where you can relax and eat in peace. It shares the rest of the garden, the barbecue area and the pool area with two other apartments.

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 103 reviews

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.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 476 reviews

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.

Guest favourite
A well-equipped kitchen features wooden cabinetry and exposed beams. Copper pots are hung on a rack, complementing tile countertops. A doorway opens to outdoor views, allowing natural light to illuminate the space.
Apartment in Castellina in Chianti
4.87 out of 5 average rating, 75 reviews

Appartamento T4

Al piano terra si trovano una cucina ben attrezzata, un salotto con caminetto (non attivo), una sala da pranzo spaziosa ed un bagno. Salendo le scale si accede al primo piano, il quale dispone di due camere da letto matrimoniali, ciascuna con bagno privato. L’appartamento T4 vanta una vista mozzafiato sulla campagna del Chianti, che si apprezza grazie al gazebo esterno con barbecue.

Popular amenities for Castellina in Chianti holiday rentals

When is the best time to visit Castellina in Chianti?

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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.