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

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

  • Villa Rosa Panzano

    Panzano
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 120 reviews

    Boasting pool with a view, garden and views of pool, Villa Rosa Panzano is located in Panzano, 11 km from Piazza Matteotti.

    From US$142.90 per night
  • Borgo Carpineto

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 512 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.

    From US$105.42 per night
  • Locanda di Pietracupa

    Tavarnelle in Val di Pesa
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    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$204.99 per night
  • Wine Resort Dievole

    Vagliagli
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 595 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.

  • 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, 394 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$92.97 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, 64 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$188.59 per night
  • 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, 117 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$172.77 per night
  • Rosso Del Chianti

    Panzano
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 411 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$172.19 per night

Highly rated holiday rentals in Castellina in Chianti and nearby

  • Scored out of 10, guest rating 8.0
    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$111.28 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 194 reviews

    Set within 18 km of Piazza Matteotti and 36 km of Piazza del Campo, Tenuta Cortedomina features rooms with air conditioning and a private bathroom in Radda in Chianti.

    From US$368.98 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 144 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$122.99 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 81 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$274.10 per night
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 446 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$143.49 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 519 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$135.21 per night
  • Casalgallo

    Quercegrossa
    8.0+ review score
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 533 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$87.85 per night
  • 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.

Enjoy breakfast in Castellina in Chianti and nearby

  • 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$141.43 per night
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 368 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$234.27 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 543 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.

    From US$306.66 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 339 reviews

    The Tenuta Il Tresto is a typical Tuscany farmhouse located in the hearth of The Chianti area, adjacent to places full of art and history such as San Gimignano, Monteriggioni and Colle di Val d’Elsa,...

    From US$89.61 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 1,235 reviews

    Set within 24 km of Piazza del Campo and 29 km of Piazza Matteotti, Agriturismo San Sano offers rooms with air conditioning and a private bathroom in Gaiole in Chianti.

    From US$127.68 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 1,007 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.

    From US$268.24 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 149 reviews

    Set in Castellina in Chianti and only 20 km from Piazza Matteotti, Mariani Bed&Breakfast offers accommodation with garden views, free WiFi and free private parking.

    From US$117.13 per night
  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 46 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$117.13 per night

FAQ about holiday rentals in Castellina in Chianti

Holiday rentals that guests love in Castellina in Chianti

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  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 180 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$284.50
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 991 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
  • Avg. price/night: US$165.83
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 713 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
  • Avg. price/night: US$501.34
    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$284.50
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 991 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$284.50
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 991 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