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Vacation rentals in Castellina in Chianti

Find and book unique accommodations on Airbnb

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

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
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 out of 5 average rating, 340 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults, with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards, with incomparable sunsets.

Top guest favorite
Apartment in Castellina in Chianti
4.94 out of 5 average rating, 53 reviews

Casa Mirella in Chianti

Nestled among the rolling Tuscan hills, our apartment is the ideal choice for those who want to experience an authentic stay in the Chianti Classico region. The terrace offers a relaxing space where you can enjoy a glass of wine while admiring the view. The location is strategic: 28 km from Siena and 45 km from Florence, in the heart of medieval villages, among renowned wineries, farms and suggestive Etruscan tombs, to be visited by those who love history and culture. Experience the most authentic Tuscany: we look forward to seeing you!

Top guest favorite
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
4.94 out of 5 average rating, 250 reviews

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Top guest favorite
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 in Castellina in Chianti
5 out of 5 average rating, 16 reviews

Palazzo Bianciardi - Penthouse

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.

Guest favorite
A bright living area features a cream-colored sofa and a wooden dining table set for two. Natural light floods through a glass door leading to an outdoor area, with vibrant greenery visible outside. Artwork adorns the walls, complementing the neutral tones.
Apartment in Castellina in Chianti
4.95 out of 5 average rating, 91 reviews

"Gardenia" Apartment

The apartment is located in the new “CASA VACANZE SQUARCIALUPI” building, 100 meters from the historic center of Castellina in Chianti. Attention to detail, it is finely furnished in marble, with relaxing neutral and natural colors that recall the Provencal style. Very bright and spacious, it has an area of about 42 square meters and is spread over two floors. On foot you can reach: restaurants, wine bars, bars, banks, laundry, supermarket, clothing stores, grocery stores, baker.•

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, 223 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 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, 274 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!

Guest favorite
Castle in Tignano
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.

Top guest favorite
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, 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.

Top guest favorite
A spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home in Fiesole
4.99 out of 5 average rating, 311 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Guest favorite
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
4.86 out of 5 average rating, 73 reviews

Apartment T4

On the ground floor there is a well-equipped kitchen, a living room with a fireplace (not active), a spacious dining room and a bathroom. Going up the stairs you enter the first floor, which has two double bedrooms, each with a private bathroom. The T4 apartment boasts a breathtaking view of the Chianti countryside, which can be appreciated thanks to the outdoor gazebo with barbecue.

Top guest favorite
The stone cottage is set amidst lush greenery, featuring a sloped roof and a large glass door that opens onto a sunlit terrace. Sun loungers are positioned nearby, surrounded by flowering plants, with olive trees visible in the background against a clear blue sky.
Farm stay in Cavriglia
4.92 out of 5 average rating, 367 reviews

Chianti La Pruneta, Raphael Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

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 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 Apartment Rentals in Castellina in Chianti?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 10 homes with air conditioning, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

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