The 10 best holiday rentals in Castellina in Chianti, Italy | Booking.com
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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.

m
mariasaridou
From
Greece
The apartment was clean and spacious with all we needed for our 2 night stay. The location was within close walking distance to the town with many restaurants. Check-in via the hotel nearby, the staff was extremely friendly and helpful. You get discount in the amazing restaurant near the hotel and shop as well as free access to the hotel swimming pool that can be a nice option. The breakfast choice was excellent. The restaurant food was great with a wonderful view from the terrace.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 253 reviews
Price from
US$138.82
1 night, 2 adults
Check availability

Agriturismo La Ferrozzola

Castellina in Chianti

Set in Castellina in Chianti and only 22 km from Piazza Matteotti, Agriturismo La Ferrozzola offers accommodation with pool views, free WiFi and free private parking.

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, 179 reviews
Price from
US$153.44
1 night, 2 adults
Check availability

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, 207 reviews
Price from
US$159.80
1 night, 2 adults
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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.

C
Catherine
From
United States
Amazing, gorgeous property with very professional, friendly, and attentive staff. It's a truly magical place that is easy to fall head over heels in love with.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 224 reviews
Price from
US$247.28
1 night, 2 adults
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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.

S
Scott
From
Canada
Everything was amazing! Breakfast, staff, location, cleanliness, comfort, views, pool. This villa made our trip complete. The attention to details was amazing.
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 128 reviews
Price from
US$525.73
1 night, 2 adults
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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
Edward
From
Australia
What an outstanding place to stay. We were welcomed by a beautiful staff member who went out of her way to welcome us. The room was stunning and very comfortable. We stayed in one of the rooms (room no. 1), but there are also cottages there. We were fortunate enough to have a large bath tub as well. The room was very clean and housekeeping did a wonderful job during our stay. While there were no hot breakfast options, the breakfast was delicious. We were there for two nights so as a result we had slightly different things to eat on both days. Very happy with the food choices and the lady who was there at breakfast. The coffee was made for us and we both enjoyed two cups. The juice was so fresh. I even saw some gluten free options in packets. We drove there by car and there was a lot of parking available. It was extremely quiet as you need to drive to town. It was very peaceful. There is an outdoor pool. There is also a guest lounge that you can spend some time in. But our room was very nice so we never used the lounge room. Thank you for a lovely stay. The accommodation is lovely and your staff ensured that our stay was extremely enjoyable. The lady at reception even offered to order us pizza from a local place that delivers pizza so we didn’t need to drive anywhere. We enjoyed a lovely complementary bottle of wine as well. Thank you.
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 410 reviews
Price from
US$100.75
1 night, 2 adults
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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, 46 reviews
Price from
US$138.96
1 night, 2 adults
Check availability

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 10.0
Exceptional - What previous guests thought, 8 reviews
Price from
US$754.67
1 night, 2 adults
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AZ.AGR.POGGIO REGINI

Castellina in Chianti

Offering a garden and garden view, AZ.AGR.POGGIO REGINI is set in Castellina in Chianti, 24 km from Piazza del Campo and 27 km from Piazza Matteotti.

J
Jefferson
From
United Kingdom
Fantastic place, Maurizio and Family were very kind and gave us everything we needed!!!
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 216 reviews
Price from
US$210.76
1 night, 2 adults
Check availability

Castello di Fonterutoli Wine Resort

Castellina in Chianti

Castello di Fonterutoli Wine Resort is a medieval country village in Tuscany's Chianti wine district 5 km outside Castellina in Chianti. It offers a restaurant and wine cellar to visit.

O
Oleh
From
Ukraine
Atmosphere, view, bathroom, breakfast was amazing!
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 989 reviews
Price from
US$230.44
1 night, 2 adults
Check availability
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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These holiday rentals in Castellina in Chianti and nearby have options with free cancellation

  • Locanda di Pietracupa

    Tavarnelle in Val di Pesa
    Free cancellation options available
    Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 127 reviews

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

  • Wine Resort Dievole

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 596 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$792.07 per night

  • La Bugia del Sensale

    San Donato in Poggio
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 384 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$91.91 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, 62 reviews

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

  • Palazzo Malaspina B&B

    Tavarnelle in Val di Pesa
    Free cancellation options available
    Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 116 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.

  • Rosso Del Chianti

    Panzano
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 414 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$170.23 per night

  • Relais Santa Cristina

    Radda in Chianti
    Free cancellation options available
    Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 420 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$139.82 per night

  • Agriturismo Oliviera Winery

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 514 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$133.67 per night

Enjoy breakfast in Castellina in Chianti and nearby

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 440 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$135.40 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 538 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 8.8
    Fabulous - What previous guests thought, 192 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$115.80 per night
  • Scored out of 10, guest rating 9.3
    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$195.41 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 1,009 reviews

    Offering an outdoor pool and a restaurant, Fattoria di Cinciano is located in Poggibonsi, a 10-minute drive from the centre. Free WiFi access is available in all areas.

  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 45 reviews

    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.

    From US$115.80 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.

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

Highly rated holiday rentals in Castellina in Chianti and nearby

  • Scored out of 10, guest rating 8.0
    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$110.01 per night
  • Scored out of 10, guest rating 9.1
    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$121.59 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 82 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$270.97 per night

  • La Corte del Frate

    Panzano
    8.0+ review score
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 137 reviews

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

  • 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$86.85 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$185.28 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 132 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 8.3
    Very good - What previous guests thought, 106 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$110.01 per night

FAQ about holiday rentals in Castellina in Chianti

Holiday rentals that guests love in Castellina in Chianti

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  • Agriturismo La Ferrozzola

    Holiday Rental in Castellina in Chianti
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 179 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

  • Castello di Fonterutoli Wine Resort

    Holiday Rental in Castellina in Chianti
    Avg. price/night: US$224.65
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 989 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

  • Luxor Chianti Glamping village

    Holiday Rental in Castellina in Chianti
    Avg. price/night: US$163.94
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 714 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

  • Villa Di Capovento

    Holiday Rental in Castellina in Chianti
    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

  • Castello di Fonterutoli Wine Resort

    Holiday Rental in Castellina in Chianti
    Avg. price/night: US$224.65
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 989 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

  • Castello di Fonterutoli Wine Resort

    Holiday Rental in Castellina in Chianti
    Avg. price/night: US$224.65
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 989 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