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The best holiday homes in Castellina in Chianti

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

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Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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The holiday home with a balcony and garden views has 2 bedrooms, a living room, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a bidet. Towels and bed linen are available in the holiday home. The property has an outdoor dining area.

The beatifully refurbished stone house was amazing. It was large and comfortable. Nice outdoor sitting area.

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9.6
Exceptional
12 reviews
Price from
£235
per night

The holiday home with a patio and garden views features 2 bedrooms, a living room, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 1 bathroom with a walk-in shower. Towels and bed linen are featured in the holiday home. There is also a seating area and a fireplace.

The contact and check in via Whatsapp was very detailed. The house is really beautiful and very clean. There was everything you need and eveything a household needs and when we got a question the answer came really fast. The stay was really perfect and we will come back with pleasure. The village is 30 minutes away by walking and you can get everything there, so the house and the location is beautiful and nearly perfect. I can rellay recommend a stay here.

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9
Superb
22 reviews
Price from
£142
per night

The holiday home is equipped with 2 bedrooms, 1 bathroom, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a terrace with garden views. The property has an outdoor dining area.

The house is lovely in a very nice and quiet location! It’s close enough to the village though. Bedrooms were good with good beds, everything you need you is there in the kitchen, spacious and modern bathroom. Very good communication with the owner. We loved our stay and were sad we had to leave!

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9.4
Superb
17 reviews
Price from
£171
per night

The units are equipped with air conditioning, a dishwasher, an oven, a coffee machine, a bidet, a hair dryer and a desk. Featuring a private bathroom with a shower and free toiletries, units at the holiday home also offer free WiFi. At the holiday home, all units come with bed linen and towels.

Cipressini is a gem. It is not only the setting in a historical tuscan farm, it is also about Pia, the owner. She was so helpful on every litlle thing and treating us like family. Everything is perfect at Cipressini!

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9.9
Exceptional
22 reviews
Price from
£284
per night

Featuring air-conditioned accommodation with a pool with a view, La Misura cottage with swimming pool is set in Castellina in Chianti. Both free WiFi and parking on-site are accessible at the holiday home free of charge. The property is non-smoking and is located 14 km from Piazza Matteotti.

Best equipped vacation home we have ever been to. Beautiful interior with a lot of love to detail. Private yard to relax, have barbecue and enjoy the stay.

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9.5
Exceptional
13 reviews
Price from
£187
per night

The spacious holiday home has 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a bidet, a hair dryer and a washing machine. Guests can take in the ambience of the surroundings from an outdoor dining area or keep themselves warm by the fireplace on colder days. For added privacy, the accommodation features a private entrance.

view was spectacular. pool was nice, but too cool in October to use.

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9.1
Superb
25 reviews
Price from
£267
per night

This holiday home has 2 bedrooms, a kitchen with a dishwasher and an oven, a flat-screen TV, a seating area and 2 bathrooms. Towels and bed linen are offered in the holiday home. The property has an outdoor dining area.

An absolutely stunning property set in a peaceful location. The property was clean and comfortable and the host was kind and accommodating. We will definitely return here on our next travels.

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9.6
Exceptional
10 reviews
Price from
£165
per night

The holiday home with a terrace and garden views has 2 bedrooms, a living room, a TV, an equipped kitchen with an oven and a microwave, and 1 bathroom with a walk-in shower. Towels and bed linen are available in the holiday home. For added privacy, the accommodation has a private entrance and is protected by full-day security.

Location and the property were brilliant. A Tuscan Villa with space inside and outside to relax and enjoy the scenery. As we travelled with car the location is brilliant for Pisa - Siena - Florence and everything in between. We we looked after with all our needs and would recommend this to anyone. We had the car so some days drove out for dinner, other the facilities are there to cook at home and also the hotel nextdoor (300m) has a restaurant which you can walk to if you wanted to relax and not drive. Rooms both generous in size and the bonus of the sofas and lounge area plus the outdoor lounge area is great.

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9.5
Exceptional
35 reviews

Situated in Castellina in Chianti, Villetta Adelma Fioraie features accommodation with a private pool, a balcony and garden views. This property offers access to a terrace, free private parking and free WiFi. Pitti Palace is 39 km away and Strozzi Palace is 40 km from the holiday home.

Very nice hosts, helpful and you could count on them. The house is well-maintained, quite clean, although you can see that some furniture, especially on the ground floor in the living room, would need renovation. Nice swimming pool and well-kept plot.

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8.1
Very good
7 reviews
Price from
£352
per night

Boasting a DVD player, the holiday home has a fully equipped kitchen with a dishwasher, an oven and a microwave, a living room with a seating area and a dining area, 2 bedrooms, and 1 bathroom with a bidet and a shower. The unit is air conditioned and is comprised of a terrace with an outdoor dining area as well as a flat-screen TV with satellite channels. The accommodation offers a fireplace.

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8.6
Fabulous
7 reviews
Price from
£113
per night

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
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Most booked holiday homes in Castellina in Chianti this month

Enjoy breakfast in Castellina in Chianti!

  • CASA IL MANDORLO NEL CHIANTI
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 22 reviews

    Located in Castellina in Chianti and only 21 km from Piazza del Campo, CASA IL MANDORLO NEL CHIANTI provides accommodation with inner courtyard views, free WiFi and free private parking.

    The apartment is quiet and clean. the location is good if you drive car to explore the area.

  • Casa VANINA-self check-in
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 17 reviews

    Located in Castellina in Chianti in the Tuscany region and Piazza del Campo reachable within 21 km, Casa VANINA-self check-in provides accommodation with free WiFi, barbecue facilities, a garden and...

    Sehr schönes Haus und sehr schöne, abgeschiedene Lage

  • Cipressini
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 22 reviews

    Located within 22 km of Piazza Matteotti and 24 km of Piazza del Campo in Castellina in Chianti, Cipressini provides accommodation with seating area.

    Great place, very nice owner, amazing pool, very well equipped beautiful house

  • La Misura cottage with swimming pool
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 13 reviews

    Featuring air-conditioned accommodation with a pool with a view, La Misura cottage with swimming pool is set in Castellina in Chianti.

    Cudowne miejsce na odpoczynek. Z dala od zgiełku miast.

  • CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 25 reviews

    Situated in Castellina in Chianti, CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL features accommodation with pool with a view, free WiFi and free private parking for guests who drive.

    Fantastic location, helpful owner, beautiful view!

  • casa vacanze nel Chianti il Granaio
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 10 reviews

    Situated in Castellina in Chianti and only 33 km from Piazza Matteotti, casa vacanze nel Chianti il Granaio features accommodation with pool views, free WiFi and free private parking. 38 km from...

    Posto incantevole, meraviglioso! Proprietari super gentili

  • Salto di Gatto
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 35 reviews

    Situated in Castellina in Chianti, in a historic building, 15 km from Piazza del Campo, Salto di Gatto is a holiday home with a garden and barbecue facilities.

    Geschmackvolle Einrichtung, einfach, aber sehr liebevoll!

  • Villetta Adelma Fioraie
    8.1
    Scored 8.1
    Very good
    Rated very good
     · 7 reviews

    Situated in Castellina in Chianti, Villetta Adelma Fioraie features accommodation with a private pool, a balcony and garden views.

    Wir würden immer wieder kommen! Geniale Aussicht, tolles Haus!

Save money on holiday homes in Castellina in Chianti – budget options available!

  • Villetta La Miniera
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 7 reviews

    Situated in Castellina in Chianti in the Tuscany region, Villetta La Miniera features accommodation with free WiFi and free private parking.

    Pool war recht schön, aber man musste über eine Staubstraße ca. 200 m gehen.

  • Casa il Cipresso, in the heart of Chianti with swimming pool
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 9 reviews

    Set 14 km from Piazza Matteotti, Casa il Cipresso, in the heart of Chianti with swimming pool has a seasonal outdoor pool, free WiFi, and free private parking for guests who drive.

  • Holiday Home Cignanbianco - Tramonto by Interhome
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 8 reviews

    Boasting air-conditioned accommodation with a patio, Holiday Home Cignanbianco - Tramonto by Interhome is situated in Castellina in Chianti.

    De locatie is schitterend en de faciliteiten in het huis is prima.

  • Holiday Home Cellole - Valluccia by Interhome
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 7 reviews

    Boasting garden views, Holiday Home Cellole - Valluccia by Interhome features accommodation with a patio, around 23 km from Piazza del Campo.

    Het uitzicht,het zwembad, de natuur en de rust rondom ons...

  • The House , Tuscany and the pool
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Located in Castellina in Chianti, The House, Tuscany and the pool provides accommodation with a private pool, a patio and garden views.

  • Bellosguardo 8
    Budget options available

    Located in Castellina in Chianti, Bellosguardo 8 provides a private pool. This property offers access to a balcony, free private parking and free WiFi. Outdoor dining is also possible at the villa.

  • Casa Chianti Classico, Panoramic View - Happy Rentals
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Set in Castellina in Chianti in the Tuscany region, Casa Chianti Classico, Panoramic View - Happy Rentals has a terrace. Situated 21 km from Piazza del Campo, the property offers a garden.

  • Il Villino Farmhouse
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews

    Situated in Castellina in Chianti, in a historic building, 19 km from Piazza del Campo, Il Villino Farmhouse is a recently renovated holiday home with a garden and barbecue facilities.

Great access to the city centre! Check these holiday homes in Castellina in Chianti

  • Cottage San Bartolomeo
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Offering a garden and garden view, Cottage San Bartolomeo is set in Castellina in Chianti, 22 km from Piazza del Campo and 45 km from Pitti Palace.

  • Casa Fioraie by PosarelliVillas
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Located in Castellina in Chianti, 27 km from Piazza Matteotti and 29 km from Piazza del Campo, Casa Fioraie by PosarelliVillas offers a terrace and air conditioning.

  • Bellosguardo
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Set in Castellina in Chianti, Bellosguardo provides a private pool. This property offers access to a balcony, free private parking and free WiFi.

  • Casa Gosi
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 12 reviews

    Situated in Castellina in Chianti, 20 km from Piazza del Campo and 21 km from Piazza Matteotti, Casa Gosi offers a garden and air conditioning.

    maison ancienne bien rénovée avec tout l'équipement

  • Holiday Home Cignanbianco - Alba by Interhome
    8.0
    Scored 8.0
    Very good
    Rated very good
     · 4 reviews

    Located in Castellina in Chianti, 50 km from Pitti Palace, Holiday Home Cignanbianco - Alba by Interhome features accommodation with access to a garden.

  • Chianti Suite
    7.8
    Scored 7.8
    Good
    Rated good
     · 39 reviews

    Located in Castellina in Chianti, 17 km from Piazza del Campo, Chianti Suite provides accommodation with an infinity pool, free private parking, a garden and a terrace.

    location is exceptionnal, swimming pool beautiful and very charming moment

  • Holiday Home Casa Chiara by Interhome
    7.0
    Scored 7.0
    Good
    Rated good
     · 4 reviews

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

  • Casa Antico Roseto with swimming pool
    7.0
    Scored 7.0
    Good
    Rated good
     · 5 reviews

    Boasting a garden, pool with a view and garden views, Casa Antico Roseto with swimming pool is situated in Castellina in Chianti.

  • Villa Delle Upupe 8, Emma Villas
    6.5
    Scored 6.5
    Pleasant
    Rated pleasant
     · 2 reviews

    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.

  • Casa Belvedere cottage with swimming pool
    6.5
    Scored 6.5
    Pleasant
    Rated pleasant
     · 2 reviews

    Set in Castellina in Chianti, Casa Belvedere cottage with swimming pool offers accommodation with pool with a view, free WiFi and free private parking for guests who drive.

  • Holiday Home Olivo by Interhome

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

  • Casanovina

    Featuring accommodation with a private pool, Casanovina is located in Castellina in Chianti. This property offers access to a balcony, free private parking and free WiFi.

  • Casale Cipressi

    Located in Castellina in Chianti, Casale Cipressi offers a patio with garden and quiet street views, as well as a seasonal outdoor pool, sauna and spa facilities.

  • Macia Viva

    Featuring air-conditioned accommodation with a private pool, Macia Viva is set in Castellina in Chianti. This property offers access to a balcony, free private parking and free WiFi.

  • Casale Sandonatino by VacaVilla

    Boasting garden views, Casale Sandonatino by VacaVilla features accommodation with a balcony, around 22 km from Piazza Matteotti.

  • Casale Cipressi

    Located in Castellina in Chianti, Casale Cipressi provides a private pool. This property offers access to a balcony, free private parking and free WiFi. Outdoor dining is also possible at the villa.

  • Villa La Casina

    Featuring air-conditioned accommodation with a private pool, Villa La Casina is located in Castellina in Chianti.

  • Villa Castellina - Homelilke Villas

    Boasting air-conditioned accommodation with a private pool, Villa Castellina - Homelilke Villas is situated in Castellina in Chianti.

  • Ginestra

    Set in Castellina in Chianti in the Tuscany region, Ginestra features a balcony. Both free WiFi and parking on-site are available at the villa free of charge.

  • Antico Cipresso

    Located in Castellina in Chianti in the Tuscany region, Antico Cipresso features a balcony. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

  • Casetta Erika

    Situated in Castellina in Chianti, Casetta Erika features a private pool. This property offers access to a balcony, free private parking and free WiFi. Outdoor dining is also possible at the villa.

  • Villa La Corte Di Campalli

    Located in the Chianti area, Villa La Corte Di Campalli is approximately a 20-minute drive from Siena and less than a 1-hour drive from Florence.

  • Casa Anita - pool and tennis court Castellina in Chianti - Granaio, Toscana

    Situated in Castellina in Chianti and only 33 km from Piazza Matteotti, Casa Anita - pool and tennis court Castellina in Chianti - Granaio, Toscana features accommodation with garden views, free WiFi...

FAQ about holiday homes in Castellina in Chianti






Holiday homes that guests love in Castellina in Chianti

  • 9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 2 reviews
    The flat is new, very clean, fully equipped with everything one needs.
    Marta
    Young couple
  • Avg. price/night: £164.88
    8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 842 reviews
    Super quaint beautiful getaway, great food and wine in restaurant nearby, the hotel itself is very clean and elegantly designed rooms and communal areas only add to the charm of this beautiful place. It's c.a. an hour drive from Florence. All the usual amenities, lovely staff and great service!
    Ksenia
    Young couple
  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 309 reviews
    We really enjoyed our stay, we had the two bedroom appartment for 3 nights. Staff was amazing and went the extra mile for us - we stayed there when they were closing the relais, but were very nice offering us breakfast in the room and even re-opened the restaurant for us. The place is very clean, well maintained, staff is amazing and food is great. The views are amazing and the wine, honey and oil produced at Fizzano are some of the best I tasted❤️.
    Mihaela
    Family with young children
  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 273 reviews
    Very clean and comfy accomodation. Our landlord- Kristína was helpfull and entertaining. I highly recommend the place.
    Julka Fristikova
    People with friends
  • 9.1
    Scored 9.1
    Superb
    Rated superb
     · 660 reviews
    Very cute and quaint place. Lovely room, very clean and tidy. Great breakfast selection and lovely location.
    Guy
    Young couple
  • 9.1
    Scored 9.1
    Superb
    Rated superb
     · 660 reviews
    Beautiful hotel, surrounded by vineyards and a small town with small shops and restaurants. the rooms are beautiful and spacious and they have great country side style, very clean and have amazing views. The breakfast is really good and varied. !The staff is very friendly and helpful and the spa is really nice. We enjoyed our staying very much
    מיכאל
    Young couple
  • 9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 57 reviews
    It was such a beautiful stay we had at this cute winery. Our host and her dog are the cutest, we enjoyed a wine tour and tasting. The apartment has a exceptional view over the wine yards and also has super cute interior and a nice terrace. Also the pool was very clean and a wonderful spot to relax in the middle of Tuscany. We will definitely come back.
    Georg
    Young couple
  • 9.1
    Scored 9.1
    Superb
    Rated superb
     · 26 reviews
    Stone building with the character of Chianti. Compact, very clean with lots of equipment and facilities to make it home from home. Great outside space with tables, chairs for dining and loungers for relaxing. Lots of space for parking directly outside. Owner very responsive to any queries.
    Paul
    Young couple
  • Avg. price/night: £83.29
    7.8
    Scored 7.8
    Good
    Rated good
     · 400 reviews
    House was old and authentic but very clean and cozy.
    Darko
    Young couple
  • Avg. price/night: £147.88
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 686 reviews
    So friendly. Lovely pool. Great location and very clean.
    Pieter
    Family with young children
gogless