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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.

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, 239 reviews
Price from
US$139.22
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.

j
julie
From
France
Very charming accommodation in the middle of vineyards. The location is very scenic, especially at sunset. The apartment is vast and beautiful, only rustic in appearance as the wifi, heating and other amenities work perfectly well.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 181 reviews
Price from
US$153.87
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
Agnieszka
From
Poland
This place is absolutely stunning - even much better than on the pictures Apartments are very clean and comfortable and have top quality of furnitures and textiles All the amenities around the house are very well designed - the pool, bar, garden, you will have a peaceful stay with a beautiful view on the vineyards and the town Nearby town is lovely, great local shops and good restaurants
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 211 reviews
Price from
US$160.26
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.

P
Petra Borst
From
Netherlands
Fantastic location to stay. Close to Castellina, in the middle of nature and super quiet. The views from both the terrace and swimmingpool area are amazing. Very friendly and helpful staff. Excellent breakfast, would definitely recommend to book this place with breakfast. The apartment was very spacious and cosy, comfortable bed, good size bathroom, very clean. We did a wine tasting, I would also definitely recommend to do that, super nice. We didn’t want to leave :-)
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 212 reviews
Price from
US$247.98
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.

K
Kaewalee
From
Thailand
- Villa interior design and natural and trekking way around. - Facilities and service - Yummy Meals both breakfast and dinner - Cozy and homy feelings
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 126 reviews
Price from
US$428.52
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$143.42
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.

P
Piotr
From
Poland
Amazing view and lovely infinity pool
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 397 reviews
Price from
US$101.03
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.

M
MIRCEA
From
Romania
The host is very careful. The place is great, very clean, spatious, with a fine touch of an artist Wonderful
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 47 reviews
Price from
US$127.74
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
Boom
From
Netherlands
Quiet, comfortable, and cozy appartment with a fabulous view on the huge balcony (+20 m²).
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 45 reviews
Price from
US$150.97
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$756.82
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 9.0
Superb - What previous guests thought, 211 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 239 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 441 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 9.1
Superb - What previous guests thought, 212 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, 218 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 454 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 9.1
Superb - What previous guests thought, 397 reviews

Popular with guests booking holiday rentals in Castellina in Chianti

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,013 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$174.19 per night
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 153 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$155.70 per night
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 435 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.

Scored out of 10, guest rating 9.5
Exceptional - 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$164.03 per night

Rosso Del Chianti

Panzano
Breakfast options
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 418 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$170.71 per night
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 412 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$140.22 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 378 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$203.23 per night

Holiday Rentals with swimming pools in Castellina in Chianti and nearby

Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 514 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$58.07 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$266.52 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 531 reviews

Featuring pool with a view and views of garden, Castello di Volpaia is a country house situated in a historic building in Radda in Chianti, 22 km from Piazza Matteotti.

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$110.32 per night

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

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 441 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.

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.

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, 372 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$80.05 per night

old medieval apartment

San Donato in Poggio
Free cancellation options available
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 59 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$186.97 per night

La Corte del Frate

Panzano
Free cancellation options available
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 141 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$68.11 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$185.81 per night

Residenza Antico Chianti

Panzano
Free cancellation options available
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 134 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$130.65 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$116.13 per night

Villa Sofia & Spa

Gaiole in Chianti
Free cancellation options available
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 73 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.

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.

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$116.13 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$92.90 per night
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, 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, 118 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, 397 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.

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$153.87
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$225.29
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,013 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 9.9
Exceptional - What previous guests thought, 126 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$225.29
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,013 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$225.29
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 1,013 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