
Holiday rentals in Castellina in Chianti
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Top-rated holiday rentals in Castellina in Chianti
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Villa di Geggiano - Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Original Tuscan Experience in the Heart of Chianti
Exclusive historic estate in the heart of Chianti Classico, where luxury meets authentic Tuscan charm. Nestled among centuries-old vineyards and breathtaking hills, this 16th-century property offers an unforgettable experience for discerning guests. Three masterfully restored bedrooms and contemporary comforts of the highest standard. Just 30 minutes from Florence and Siena, the estate is the perfect retreat for those seeking absolute privacy, timeless beauty and the purest essence of Tuscany.

Tramonto sul Chianti Classico
Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

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

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!

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.•

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.

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.

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.

Live the Tuscany Experience in Our Country House
An amazing experience between nature, flavor and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

Open Space Piscina e Giardino
La mia casa è immersa nella campagna toscana, tra olivi e vigne, nel cuore del Chianti. Intorno, panorami meravigliosi e un’atmosfera di pace e relax. Il giardino è uno spazio speciale, ideale per momenti da vivere all’aperto. Per chi lo desidera, è possibile – su richiesta – condividere esperienze legate alla cucina e alla convivialità, come cene preparate con cura, da gustare insieme, anche a lume di candela, in un contesto intimo e accogliente.
Popular amenities for Castellina in Chianti holiday rentals
Other great holiday rentals in Castellina in Chianti

AnticaVista, Luxury Apartment with Tower Views

Country House Lo Spigo 4, Emma Villas

Sogno Toscano a Fonterutoli tra Siena e il Chianti

Tuscany jem: La Casa del Fattore del Chianti

Tuscan Luxury Villa • Natural Pool & Privacy

a.d. 1237

pittoresca colonica, chianti, giardino panoramico

Podere Tignano, 4-bedroom villa in the Chianti!
When is the best time to visit Castellina in Chianti?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $197 SGD | $194 SGD | $212 SGD | $214 SGD | $215 SGD | $232 SGD | $227 SGD | $228 SGD | $239 SGD | $219 SGD | $197 SGD | $195 SGD |
| 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
Are there pet-friendly vacation rentals in Castellina in Chianti?
Four-legged friends are welcome in Castellina in Chianti. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Castellina in Chianti?
Yes! Work meets play with ease at over 20 vacation rentals in Castellina in Chianti featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Castellina in Chianti vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Castellina in Chianti, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Castellina in Chianti?
Castellina in Chianti has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in bed and breakfast rentals in Castellina in Chianti?
Experience the best of Castellina in Chianti with our bed and breakfast rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Castellina in Chianti have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Castellina in Chianti have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Castellina in Chianti have wifi?
Absolutely! We offer over 10 house rentals with wifi in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Castellina in Chianti have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Castellina in Chianti?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 $64 SGD per night before taxes and fees

Verified guest reviews
Over 1,270 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 of Castellina in Chianti holiday rentals include wifi 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
Destinations to explore
- Rentals with a patio Castellina in Chianti
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- Rentals with outdoor seating Castellina in Chianti
- Pet-friendly rentals Castellina in Chianti
- Flat rentals Castellina in Chianti
- Rentals with pools Castellina in Chianti
- Rentals with a washing machine and dryer Castellina in Chianti
- Rentals with a fireplace Castellina in Chianti
- House rentals Castellina in Chianti
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- Cathedral of Santa Maria del Fiore
- Lake Trasimeno
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Cala Violina
- Mercato Centrale
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Stazione Santa Maria Novella
- Del Chianti
- Piazza della Repubblica
- Spiagge Bianche
- Piazzale Michelangelo
- Parco delle Cascine
- Pitti Palace
- Piazza della Signoria
- Boboli's Garden
- Palazzo Vecchio





