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Vacation rentals in Castellina in Chianti

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Top-rated vacation rentals in Castellina in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 498 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Guest favorite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 131 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favorite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 234 reviews

The Chianti Classico Sunset

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.

Top guest favorite
The swimming pool features clear blue water, inviting for relaxation. A shaded gazebo is positioned nearby with lounge chairs arranged for comfort. Rolling hills with greenery surround the area, offering a peaceful backdrop against a partly cloudy sky.
Cottage in Castellina in Chianti
4.96 out of 5 average rating, 106 reviews

Vittoria Cottage - Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Cappero (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Top guest favorite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni
4.95 out of 5 average rating, 284 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 217 reviews

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.

Top guest favorite
A large swimming pool is featured, reflecting the clear blue sky above. Olive trees line the surrounding area, creating a serene outdoor environment. The water's surface appears serene and inviting, emphasizing relaxation amidst the natural landscape.
Home in Castellina in Chianti
4.98 out of 5 average rating, 130 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 favorite
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
4.92 out of 5 average rating, 269 reviews

Casa al Gianni - Hut

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!

Top guest favorite
An expansive terrace showcases a dining table set for six, complemented by comfortable seating. A shaded canopy provides relief from the sun, while surrounding greenery enhances the atmosphere. Panoramic views of Florence are visible in the background, underscoring an inviting outdoor space.
Condo in Santo Spirito
5 out of 5 average rating, 112 reviews

Exclusive Florence Penthouse with city views

The truly Florentine soul of this exquisite apartment and its panoramic terrace sets the stage for an unforgettable stay. From this privileged vantage point above the rooftops, you can almost touch Florence’s monuments as you sip a sunset aperitivo, or greet the morning beneath the pergola with a leisurely breakfast while the city awakens in golden light.

Top guest favorite
An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.
Castle in Barberino Tavarnelle
4.89 out of 5 average rating, 124 reviews

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Guest favorite
A clear swimming pool reflects the sky, surrounded by lounge chairs and sun umbrellas, set against the backdrop of a rustic stone building. Lush greenery completes the serene outdoor space.
Apartment in Castellina in Chianti
4.91 out of 5 average rating, 134 reviews

Casa Tatini your house in Chianti

Casa Tatini is in the heart of Chianti just 500 meters from Castellina in Chianti in the middle of the vines and nature, to relax in the greenery. The house, equipped with swimming pool, consists of a double bedroom, living room with kitchen and private bathroom.

Top guest favorite
A historic stone structure is surrounded by greenery, featuring large windows and a staircase leading to an entrance. Delicate pink flowers bloom on nearby trees, adding a touch of color to the natural setting. The rustic walls complement the tranquil atmosphere.
Home in Monticchiello
4.98 out of 5 average rating, 215 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Popular amenities for Castellina in Chianti vacation rentals

When is the best time to visit Castellina in Chianti?

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Avg. priceﺩ.ﺇ 566ﺩ.ﺇ 555ﺩ.ﺇ 606ﺩ.ﺇ 613ﺩ.ﺇ 617ﺩ.ﺇ 665ﺩ.ﺇ 650ﺩ.ﺇ 654ﺩ.ﺇ 683ﺩ.ﺇ 628ﺩ.ﺇ 566ﺩ.ﺇ 558
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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 house rentals in Castellina in Chianti?

    Experience the best of Castellina in Chianti with our house rentals, starting at about $50 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 apartment rentals in Castellina in Chianti have wifi?

    Absolutely! We offer over 20 apartment 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 a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Castellina in Chianti

  • Total vacation rentals

    Explore 70 vacation rentals in Castellina in Chianti

  • Nightly prices starting at

    Castellina in Chianti vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 1,270 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Castellina in Chianti vacation 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

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