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Holiday Rentals in Castellina in Chianti

Find the holiday rentals that appeal to you the most

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.

K
Kit Yan
From
Hong Kong
A perfect stay with stunning view.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 237 reviews
Price from
US$137.88
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.

R
Randi
From
Norway
A stunningly beautiful place with views over olive groves and vineyards. So much charm and lovely details throughout. The view is unrealistically beautiful – it feels like a dream!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 181 reviews
Price from
US$152.39
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.

A
Anna
From
Sweden
Nice and quite vinery with good wine outside Castellina
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 211 reviews
Price from
US$158.72
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.

T
Timothy Batchelder
From
United Kingdom
perfect location with stunning views of the vineyards. perfect for a romantic getaway like wedding anniversary celebration.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 211 reviews
Price from
US$245.60
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.

E
Efraim
From
Sweden
Literally everything, from the very first second after parking Ettore and Stella were there to welcome us and we felt their kindness and great hosting through the whole stay. Such a lovely, peaceful place and surroundings to be at. I'd without a doubt come back!
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 127 reviews
Price from
US$549.77
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.

N
Nina
From
Slovakia
This was our second visit to this place. The quality of the accomodation and services remained excellent. We were again impressed by the beautiful Tuscany-style house and the pool.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 119 reviews
Price from
US$142.04
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.

E
Elena
From
France
Everything was absolutely perfect and amazing! The place is very beautiful, exceptional
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 398 reviews
Price from
US$100.06
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.

V
Veerle
From
Netherlands
The host Gaia was amazing and super generous! She recommended a wonderful osteria called Il Re Gallo (they parepared me a carbonara even though it wasn't on the menu), and a very cute bakery called Gastronomia Porciatti. Both are worth visiting! The apartment itself was very rustic and authentic, super spacious with amazing views from the bedroom. The location is super central as well. Will be back 100% if we're ever visiting Tuscany again!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 47 reviews
Price from
US$126.52
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.

B
Biljana
From
North Macedonia
View from big and comfy terrace, perfect bedroom, location
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 45 reviews
Price from
US$149.52
1 night, 2 adults

Luxury Serviced Cottage in a Historical Chianti Borgo

Castellina in Chianti

Boasting air-conditioned accommodation with a patio, Luxury Serviced Cottage in a Historical Chianti Borgo is situated in Castellina in Chianti.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 8 reviews
Price from
US$734.68
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, 119 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 211 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 444 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, 217 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 181 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 455 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 211 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 398 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 414 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,010 reviews

Enjoy breakfast in Castellina in Chianti and nearby

Borgo Carpineto

Vagliagli
Breakfast options
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 508 reviews

Borgo Carpineto features a hot tub and free private parking, and is within 16 km of Piazza del Campo and 30 km of Piazza Matteotti.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 124 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$172.52 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 152 reviews

Boasting pool views, Fattoria Lornano Winery offers accommodation with patio, around 15 km from Piazza del Campo. This property offers access to a terrace, free private parking and free WiFi.

From US$154.20 per night
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 114 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$163.90 per night

Rosso Del Chianti

Panzano
Breakfast options
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 416 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$169.07 per night
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 410 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$138.87 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 384 reviews

Located in Greve in Chianti, within 4.8 km of Piazza Matteotti and 32 km of Piazzale Michelangelo, Il Casello Country House provides accommodation with pool with a view and free WiFi as well as free...

From US$201.28 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 195 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$115.02 per night

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

La Bugia del Sensale

San Donato in Poggio
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 366 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$79.28 per night

Casa Panzano Tuscany

Panzano
Free cancellation options available
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$263.96 per night

La Corte del Frate

Panzano
Free cancellation options available
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 142 reviews

Featuring garden views, La Corte del Frate provides accommodation with barbecue facilities and a patio, around 8.7 km from Piazza Matteotti.

From US$67.46 per night

Torrione Apartment

Panzano
Free cancellation options available
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 29 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$184.02 per night

Residenza Antico Chianti

Panzano
Free cancellation options available
Scored out of 10, guest rating 9.0
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.

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, 444 reviews

Villa Cristina is situated in Castellina in Chianti, 20 km from Piazza Matteotti, 25 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, 515 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$64.70 per night
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 146 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$126.52 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 260 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.

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 105 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$109.26 per night
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 185 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 8.7
Fabulous - What previous guests thought, 7 reviews

Boasting air-conditioned accommodation with a balcony, CYPRESSES VILLA with PRIVATE SWIMMING POOL is situated in Castellina in Chianti.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Situated in Castellina in Chianti, Villa Delle Upupe 8, Emma Villas features accommodation with private pool, free WiFi and free private parking for guests who drive.

Highly rated holiday rentals in Castellina in Chianti and nearby

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 63 reviews

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

From US$115.02 per night

Casalgallo

Quercegrossa
8.0+ review score
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 538 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$92.01 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 16 reviews

Located within 22 km of Piazza Matteotti and 25 km of Piazza del Campo in Castellina in Chianti, Cipressini provides accommodation with seating area.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 63 reviews

Set in Castellina in Chianti in the Tuscany region and Piazza del Campo reachable within 19 km, Podere Sagna offers accommodation with free WiFi, a children's playground, a seasonal outdoor swimming...

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 9 reviews

Set in Radda in Chianti, Casa Colle Petroso offers a terrace with pool and garden views, as well as a seasonal outdoor pool, hot tub and solarium. This villa offers accommodation with a patio.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 119 reviews

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.

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 398 reviews

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.

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 21 reviews

Located in Castellina in Chianti and only 25 km from Piazza Matteotti, La Pergola provides accommodation with mountain views, free WiFi and free private parking.

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$152.39
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 181 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$223.13
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,010 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, 702 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, 127 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$223.13
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,010 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$223.13
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,010 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