Vacation rentals in Castellina in Chianti

Barn in Castellina in Chianti

A serene outdoor space features a sparkling swimming pool surrounded by lush green grass and olive trees. Several lounge chairs are positioned under large umbrellas, offering shaded areas for relaxation. The rustic stone building in the background complements the tranquil landscape.

4.97 out of 5 average rating, 36 reviews

Apartment T3

The T3 apartment has a comfortable living room with an equipped kitchen. The bedroom on the ground floor is spacious, with air conditioning, a bathroom, and French doors to the terrace overlooking the pool. The spiral staircase leads to the upper floor, equipped with another double bedroom, with the bathroom and the exit to the external driveway. The T3 apartment accommodates up to 4 people and has a breathtaking view of the Chianti countryside, which can be appreciated thanks to the outdoor gazebo with barbecue.

Villa in Castellina in Chianti

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.

4.93 out of 5 average rating, 225 reviews

The Farmhouse Cottage

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

5 out of 5 average rating, 264 reviews

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

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

A stone wall is adorned with vibrant red climbing roses, creating a striking contrast against the rustic texture. A window with a black grid pattern is visible, framed by the lush greenery of surrounding plants, enhancing the inviting character of the setting.

4.96 out of 5 average rating, 100 reviews

Leonardo - Chianti/Siena, Firenze, San Gimignano.

Ancient stone house from the 15th century in a small renovated medieval hamlet, in the heart of the Chianti Classico, located on top of a hill between Florence, Siena and San Gimignano. TENNIS COURT - SWIMMING POOL Splendid view over the valley. Independent entrance; On the ground floor: large living room with two sofas, dining area and open kitchen. On the 1st floor: 2 bedrooms and bathroom with shower; Private garden with terrace - table and chairs for eating under the gazebo and sun loungers.

4.99 out of 5 average rating, 184 reviews

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

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.

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.

4.98 out of 5 average rating, 115 reviews

StageROOM03 -Chianti Idillic Country living

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.

Farm stay in Greve in Chianti

A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.

4.99 out of 5 average rating, 385 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

4.96 out of 5 average rating, 102 reviews

The garden features a shaded dining area with a large umbrella and a wooden table set with chairs. A brick barbecue stands nearby, surrounded by greenery and well-maintained grass. The entrance to the house is visible through elegant wrought iron doors.

Cottage in La Piazza

Casa La Misura in the heart of Chianti

La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provinces of Siena and Florence. Due to its strategic position, straddling two valleys, Borgo Montecastelli enjoys a magnificent panorama from its summit towards the villages that surround it: Panzano, Radda in Chianti, Castellina in Chianti, as well as farmhouses, churches, and towers.

4.96 out of 5 average rating, 253 reviews

A set of large wooden wine barrels features a prominent yellow sign with the name 'Panzanello.' The barrels are positioned on a stone surface, surrounded by a serene landscape under a partially cloudy sky.

Condo in Panzano

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments accompanied by a good glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals.

A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.

4.98 out of 5 average rating, 103 reviews

Explore Chianti from a Charming Stone House

Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

4.9 out of 5 average rating, 210 reviews

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

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Barn in Castellina in Chianti

An infinity pool reflects the sky, surrounded by lush greenery and cypress trees. The pool's edge seamlessly blends into the landscape, overlooking rolling hills and olive groves. Sun loungers are positioned nearby, providing a serene outdoor setting.

5 out of 5 average rating, 29 reviews

Cipressini 2 - pool and amazing views

Ancient stone farmhouse 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.

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Popular amenities for Castellina in Chianti vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Castellina in Chianti

A comfortable living area featuring a light grey armchair and a matching sofa, positioned around a round wooden table. A rustic stone wall adds character, while a charming mix of decor items, including plants and a wooden chair, creates an inviting atmosphere. Natural light illuminates the space.

4.68 out of 5 average rating, 75 reviews

The House , Tuscany and the pool

Apartment in Quercegrossa

A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.

5 out of 5 average rating, 15 reviews

Tuscany gem: The Chianti Farmer's House

Cottage in Castellina in Chianti

A panoramic view of the shared swimming pool is displayed, surrounded by lush greenery and colorful flowers. Sun loungers are positioned near the pool, with a shaded seating area featuring a gazebo visible in the scene. The rolling hills of the countryside can be seen in the background.

4.84 out of 5 average rating, 37 reviews

Cottage in Chianti with a pool

An aerial view highlights a rustic stone building surrounded by lush greenery and tall cypress trees. A clear blue swimming pool is positioned adjacent to manicured gardens, featuring sun loungers and umbrellas. Olive trees dot the landscape, contributing to the serene countryside atmosphere.

Farm stay in Castellina in Chianti

4.56 out of 5 average rating, 142 reviews

Apartment LAURO with private garden

The rustic stone exterior of the house is complemented by a spacious terrace featuring a table and chairs. Surrounding greenery includes grass and olive trees, while the clear blue sky adds to the peaceful outdoor setting.

4.75 out of 5 average rating, 8 reviews

Cerretino Vigna by Interhome

Hotel room in Barberino Val d'Elsa

The image showcases a rustic stone building, formerly a mill, surrounded by lush greenery and trees. A gravel pathway leads to the entrance, where wooden windows add character. The setting is peaceful, enhanced by natural light filtering through clouds above.

4.98 out of 5 average rating, 101 reviews

Room in the Argenna Mill, Chianti, Tuscany