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Holiday Rentals in Castellina in Chianti

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The best holiday rentals in Castellina in Chianti

Check out our pick of great holiday rentals in Castellina in Chianti

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Casa Vacanze Squarcialupi

Castellina in Chianti

Offering a garden and garden view, Casa Vacanze Squarcialupi is set in Castellina in Chianti, 20 km from Piazza Matteotti and 22 km from Piazza del Campo.

N
Nicole
From
Italy
A very comfortable apartment, with everything needed, including access to the hotel pool. The position is really great for Tuscany. The staff were very friendly and helped us kindly with extra tea for the apartment. I would love to stay a week!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 249 reviews
Price from
US$139.37
1 night, 2 adults

Agriturismo La Ferrozzola

Castellina in Chianti

Featuring pool views, Agriturismo La Ferrozzola offers accommodation with patio, around 22 km from Piazza Matteotti.

C
Caroline
From
Canada
The beautiful views of vineyards and hills, we felt very welcome and on vacation. The appartment on two storeys was well decorated and the swimming pool very refreshing with a stunning view. Wow Tuscany at its best. The owners and their friendly dog were also nice. The village is closeby to get the grocery and that's where you do the check-in before arrival.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 178 reviews
Price from
US$154.04
1 night, 2 adults

Collelungo

Castellina in Chianti

Providing garden views, Collelungo in Castellina in Chianti provides accommodation, pool with a view, a garden, a bar, barbecue facilities and a shared lounge.

k
kayreenz
From
New Zealand
Collelungo, a slice of paradise in the heart of Chianti country! We took advantage of the Prima Spesa service on arrival, a great selection that fed us amply for two dinners, two breakfasts, morning, afternoon and pre-dinner snacks, and we gave away the extras to our neighbours. Fabiola is an absolute gem. We hadn't realised that there were no taxis in Castellina in Chianti and Fabiola was wonderful helping us to work around that. You really do need a vehicle here, so don't be tempted to do without one! We had a fabulous stay, sampling not only Collelungo's fine wines but those on offer from other vineyards. We also highly recommend visiting the Pomona winery which Fabiola can help arrange. Thoroughly enjoyed our pool time also and have no hesitation recommending Collelungo to anyone wanting an authentic Tuscany experience. Thank you so much Fabiola! ❤️
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 211 reviews
Price from
US$160.44
1 night, 2 adults

Querceto Di Castellina

Castellina in Chianti

Located 5 km from Castellina In Chianti, Querceto Di Castellina is a 14th-century building and offers an outdoor pool, garden and accommodation with a patio.

A
Annette
From
South Africa
The environment… tranquil, calm and beautiful. Also loved our little cottage and patio. Air con worked well during heatwave. When you are there - do Laura’s cooking workshop. Such a fun day and the food cooked was delicious.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 219 reviews
Price from
US$248.26
1 night, 2 adults

Villa Di Capovento

Castellina in Chianti

Set in the Chianti area, in the middle of the Tuscan countryside, Villa Di Capovento is an antique stone villa with outdoor pool. It is a 30-minute drive from Siena.

R
ROHIT NANANI
From
United Arab Emirates
It’s a very comfortable place with amazing hosts. We had a great time and enjoyed the breakfast and dinners served by the hosts during our stay. Also very good suggestions made by them that elevated our experience. Also they have a very good pool and very quite and secluded place.
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 128 reviews
Price from
US$527.82
1 night, 2 adults

Residenzia Del Sogno

Castellina in Chianti

The Residenzia Del Sogno is in the heart of the Chianti region, surrounded by vineyards and gardens with barbecue facilities. It offers free parking and free Wi-Fi.

A
Andrea
From
Czech Republic
We returned to this place for the third time. Amazing owners, beautiful, cozy, clean and romantic accommodation. Great quiet place.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 118 reviews
Price from
US$143.58
1 night, 2 adults

Borgo Di Pietrafitta Relais

Castellina in Chianti

Borgo di Pietrafitta Relais is situated in a delightful spot among the green Tuscan hills. Enjoy comfortable apartments between Florence 48 km away and Siena, 20 km away.

R
Rutkowska
From
Italy
Everything was perfect, the pool, the place, the calmness 🌻🤍
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 406 reviews
Price from
US$101.15
1 night, 2 adults

Palazzo Bianciardi Attico

Castellina in Chianti

Located in Castellina in Chianti, 20 km from Piazza Matteotti and 22 km from Piazza del Campo, Palazzo Bianciardi Attico provides accommodation with free WiFi in a historic building.

美華
From
Australia
It's located in middle of Castellina in Chianti. Restaurant is closed to BnB. Coop is also walkable. Host Gaia is friendy and we appreciate birthday gift.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 46 reviews
Price from
US$127.89
1 night, 2 adults

Casa Bruna - Cipresseta del Chianti

Castellina in Chianti

Featuring air-conditioned accommodation with a patio, Casa Bruna - Cipresseta del Chianti is located in Castellina in Chianti.

Х
Христина Куманова
From
Bulgaria
Lovely place and nice welcome. The directions we received were helpful to find the house. It is very pleasant to welcome the morning on the large terrace with a cup of coffee.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 45 reviews
Price from
US$151.14
1 night, 2 adults

StageROOM03 - Chianti

Castellina in Chianti

Boasting air-conditioned accommodation with a patio, StageROOM03 - Chianti is situated in Castellina in Chianti.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 8 reviews
Price from
US$757.67
1 night, 2 adults
All holiday rentals in Castellina in Chianti

Most booked holiday rentals in Castellina in Chianti and surroundings in the past month

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Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 565 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 219 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 454 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 219 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 711 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 437 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 406 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 311 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 416 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,005 reviews

Enjoy breakfast in Castellina in Chianti and nearby

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 126 reviews

Featuring city views, Locanda di Pietracupa features accommodation with a garden, a terrace and a bar, around 18 km from Piazza Matteotti.

From US$174.39 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 598 reviews

Set in 600 hectares of beautiful Chianti countryside 20 minutes from Siena, Wine Resort Dievole offers different types of recently renovated apartment-suites and rooms in a large complex.

From US$678.96 per night

La Sosta

Panzano
Breakfast options
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 223 reviews

Set within 7.1 km of Piazza Matteotti and 34 km of Ponte Vecchio, La Sosta offers rooms with air conditioning and a private bathroom in Panzano.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 441 reviews

Offering a bar and city view, Le Terrazze Del Chianti b&b Residenza d'Epoca e di Charme is situated in Tavarnelle in Val di Pesa, 32 km from Piazzale Michelangelo and 32 km from Pitti Palace.

From US$129.47 per night
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 115 reviews

Boasting a garden and views of inner courtyard, Palazzo Malaspina B&B is a bed and breakfast set in a historic building in Tavarnelle in Val di Pesa, 19 km from Piazza Matteotti.

From US$148.89 per night

Rosso Del Chianti

Panzano
Breakfast options
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 419 reviews

Offering a garden and inner courtyard view, Rosso Del Chianti is situated in Panzano, 34 km from Piazzale Michelangelo and 36 km from Ponte Vecchio.

From US$170.90 per night
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 421 reviews

The Relais Santa Cristina is a renovated country house in the heart of the Chianti wine country, outside Siena. It offers panoramic views, an outdoor pool and free parking.

From US$140.37 per night
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 510 reviews

Featuring a garden, Agriturismo Oliviera Winery is located in Vagliagli in the Tuscany region, 13 km from Piazza del Campo and 30 km from Piazza Matteotti.

From US$126.74 per night

Highly rated holiday rentals in Castellina in Chianti and nearby

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 62 reviews

Boasting quiet street views, Camere e Appartamenti Baldini Romanita provides accommodation with patio, around 18 km from Piazza Matteotti.

From US$116.26 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 145 reviews

Set in Quercegrossa, in a historic building, 14 km from Piazza del Campo, Agriturismo La Magione is an apartment with a seasonal outdoor swimming pool and garden.

From US$104.63 per night
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 383 reviews

Set just 18 km from Piazza Matteotti, La Bugia del Sensale offers accommodation in San Donato in Poggio with access to a garden, a shared lounge, as well as a shared kitchen.

From US$87.15 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 83 reviews

Boasting air-conditioned accommodation with a private pool, pool view and a balcony, Casa Panzano Tuscany is situated in Panzano. With garden views, this accommodation features a patio.

From US$272.05 per night
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 61 reviews

Located in San Donato in Poggio, 32 km from Piazzale Michelangelo and 32 km from Pitti Palace, old medieval apartment offers air conditioning.

From US$187.18 per night

Casa Volpini

Panzano
8.0+ review score
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 319 reviews

Situated within 6.3 km of Piazza Matteotti and 33 km of Ponte Vecchio, Casa Volpini features rooms with air conditioning and a private bathroom in Panzano.

From US$110.45 per night

Casalgallo

Quercegrossa
8.0+ review score
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 537 reviews

Boasting a garden and views of garden, Casalgallo is a farm stay set in a historic building in Quercegrossa, 15 km from Piazza del Campo.

From US$93.01 per night

Torrione Apartment

Panzano
8.0+ review score
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 30 reviews

Situated 8.6 km from Piazza Matteotti, 36 km from Ponte Vecchio and 36 km from Uffizi Gallery, Torrione Apartment features accommodation set in Panzano.

From US$186.02 per night

These holiday rentals in Castellina in Chianti and nearby have options with free cancellation

Residenza Antico Chianti

Panzano
Free cancellation options available
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 133 reviews

Situated in Panzano, 8.7 km from Piazza Matteotti and 36 km from Ponte Vecchio, Residenza Antico Chianti features accommodation with free WiFi in a historic building.

From US$130.79 per night

La Limonaia Country House

Monteriggioni
Free cancellation options available
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 194 reviews

Set in Monteriggioni and only 10 km from Piazza del Campo, La Limonaia Country House offers accommodation with garden views, free WiFi and free private parking.

From US$116.26 per night

Agriturismo Amina, Winery & Hiking

Vagliagli
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 255 reviews

Featuring an outdoor swimming pool and a garden with BBQ facilities and children’s playground, Agriturismo Amina, Winery & Hiking offers rooms a 5-minute drive from Vagliagli.

From US$159.86 per night

Mansarda Brunelleschi

Staggia
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 145 reviews

Offering city views, Mansarda Brunelleschi is an accommodation located in Staggia, 21 km from Piazza del Campo and 33 km from Piazza Matteotti.

From US$73.24 per night

Villa Sofia & Spa

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 72 reviews

Boasting a spa bath, Villa Sofia & Spa is set in Gaiole in Chianti. Built in 13th century, the property includes hot tub and spa centre.

From US$309.25 per night
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 7 reviews

Featuring air-conditioned accommodation with a balcony, Holiday Home Casa Chiara by Interhome is set in Castellina in Chianti.

Holiday Home Olivo by Interhome

Castellina in Chianti
Free cancellation options available

Featuring air-conditioned accommodation with a private pool, Holiday Home Olivo by Interhome is located in Castellina in Chianti.

Villa Cristina

Castellina in Chianti
Free cancellation options available
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 437 reviews

Villa Cristina is situated in Castellina in Chianti, 20 km from Piazza Matteotti, 23 km from Piazza del Campo, and 41 km from Piazzale Michelangelo.

Holiday Rentals with swimming pools in Castellina in Chianti and nearby

Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 524 reviews

Located within 33 km of Piazza del Campo and 33 km of Piazza Matteotti in Poggibonsi, Agriturismo La Moraia provides accommodation with seating area.

From US$72.66 per night
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 107 reviews

Offering pool views, Agriturismo "Crocino in Chianti" is an accommodation located in Gaiole in Chianti, 26 km from Piazza del Campo and 27 km from Piazza Matteotti.

From US$110.45 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 182 reviews

Podere Palazzolo is a country farmhouse set outside Castellina in Chianti. It has large gardens with swimming pool overlooking the Chianti Valley. Parking and Wi-Fi are free.

Situated in Castellina in Chianti, Casanovina provides a private pool. This property offers access to a terrace and free private parking.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews

Featuring garden views, Apartment Cellole - Cellole 1 - CTC150 by Interhome provides accommodation with a seasonal outdoor swimming pool and a patio, around 21 km from Piazza Matteotti.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 7 reviews

Boasting garden views, Apartment Cellole - Torretta - CTC153 by Interhome offers accommodation with a seasonal outdoor swimming pool and a patio, around 21 km from Piazza Matteotti.

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 12 reviews

Boasting garden views, Apartment Cellole - Cellole 2 - CTC151 by Interhome offers accommodation with a seasonal outdoor swimming pool and a patio, around 21 km from Piazza Matteotti.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 2 reviews

Boasting garden views, Apartment Cellole - La Stalla by Interhome features accommodation with a seasonal outdoor swimming pool and a patio, around 21 km from Piazza Matteotti.

FAQ about holiday rentals in Castellina in Chianti

Holiday rentals that guests love in Castellina in Chianti

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Avg. price/night: US$154.04
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 178 reviews
The beautiful views of vineyards and hills, we felt very welcome and on vacation. The appartment on two storeys was well decorated and the swimming pool very refreshing with a stunning view. Wow Tuscany at its best. The owners and their friendly dog were also nice. The village is closeby to get the grocery and that's where you do the check-in before arrival.
Guest review by
Caroline
Young couple
Avg. price/night: US$266.24
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,005 reviews
We loved staying at the wine resort! It was a beautiful place in Tuscany. We would love to visit again someday. The old villas were modernized and reconditioned with modern amenities very nicely. Our stay was very charming and delightful.
Guest review by
Robert
Family with young children
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 711 reviews
- bathrooms are clean - towels and bed linen were clean and pleasant - large swimming pool - tasty food in the restaurant, but there was a small selection of different dishes - a very nice place in a nice location, perfectly close to the vineyard - great vineyard Tenuta Villa Trasqua right next door I highly recommend wine tasting there
Guest review by
Malgorzata
Family with young children
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 128 reviews
Stella and Ettore were such amazing hosts! From the super clean villa and the mouthwatering breakfast and dinners, they made the best stay for us! Close to several nearby towns, and a short distance to Sienna for sight seeing, food and shopping. Convenience, location, the views, and welcoming feel will have us back should we return to the Chianti area in the future! Thanks for having us and being the best hosts!!!
Guest review by
Danielle
Young couple
Avg. price/night: US$266.24
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,005 reviews
Very nice village/location, picturesque, nice breakfast, beautiful breakfast area, clean and comfortable. Very nice bathroom amenities.
Guest review by
ElisavetArgiris
People with friends
Avg. price/night: US$266.24
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,005 reviews
Excellent resort located in Castellina in Chianti, rooms were cosy and comfortable. Friendly and attentive staff. Castellina seems to be a village from a fairytale- unbelievably beautiful. The wine bar located next to the reception and delicious food in the restaurant nearby. Highly recommended!
Guest review by
Natalia
People with friends