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Holiday rentals in Castellina in Chianti

Find and book unique accommodation on Airbnb

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 £37 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

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
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage
4.99 out of 5 average rating, 153 reviews

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.

Top 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
4.94 out of 5 average rating, 250 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
A spacious bedroom features a high ceiling with exposed wooden beams and terracotta tiles. A large bed is complemented by two nightstands with lamps. A wooden dresser and a small table are visible, adding functionality to the serene space. Natural light brightens the room.
Loft
5 out of 5 average rating, 16 reviews

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.

Top guest favourite
Flat
4.94 out of 5 average rating, 53 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
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.
Apartment
5 out of 5 average rating, 340 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica e storica proprietà risalente al 1600 situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare servizio navetta e esperienze esclusive su misura per voi . 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 colline e vigneti con tramonti unici.

Guest favourite
The spacious living area features natural stone flooring and a charming dining table surrounded by four chairs. Light pours in through large windows, offering views of the outdoor patio. A glass door provides access to the garden, enhancing the inviting atmosphere.
Flat
4.88 out of 5 average rating, 77 reviews

Gelsomino

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.•

Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home
4.98 out of 5 average rating, 181 reviews

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!

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
4.98 out of 5 average rating, 131 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.

Guest favourite
Castle
5 out of 5 average rating, 24 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.

Superhost
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.
Apartment
4.88 out of 5 average rating, 92 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 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
4.99 out of 5 average rating, 475 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.
Flat
4.86 out of 5 average rating, 73 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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Avg. price£115£113£123£125£125£135£132£133£139£128£115£113
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°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 apartment rentals in Castellina in Chianti have a kitchen?

    Absolutely! We offer over 20 apartment rentals with a kitchen in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Castellina in Chianti have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Castellina in Chianti. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Castellina in Chianti have free parking?

    Absolutely! We offer over 10 house 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 free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

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