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The best vacation homes in Castellina in Chianti

Check out our selection of great vacation homes in Castellina in Chianti

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Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

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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
£232
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
Wonderful
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
Wonderful
17 reviews
Price from
£152
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
£253
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
£130
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
Wonderful
25 reviews
Price from
£187
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
£169
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
36 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
£328
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
Excellent
7 reviews
Price from
£112
per night

Looking for a vacation home?

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

Enjoy breakfast in Castellina in Chianti!

  • CASA IL MANDORLO NEL CHIANTI
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 22 reviews

    CASA IL MANDORLO NEL CHIANTI is located in Castellina in Chianti, just 13 miles from Piazza del Campo and 14 miles from Piazza Matteotti.

    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
    Wonderful
    Rated wonderful
     · 17 reviews

    Featuring a garden, Casa VANINA-self check-in features accommodations in Castellina in Chianti. The vacation home features both Wifi and private parking free of charge.

    Sehr schönes Haus und sehr schöne, abgeschiedene Lage

  • Cipressini
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 22 reviews

    Providing garden views, Cipressini in Castellina in Chianti provides accommodations and a garden. This property offers a pool with a view, free Wifi, and free private parking.

    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

    La Misura cottage with swimming pool offers accommodations in Castellina in Chianti, 8.8 miles from Piazza Matteotti and 20 miles from Piazza del Campo.

    Cudowne miejsce na odpoczynek. Z dala od zgiełku miast.

  • CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 25 reviews

    CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL is located in Castellina in Chianti, just 8.8 miles from Piazza Matteotti and 20 miles from Piazza del Campo.

    Fantastic location, helpful owner, beautiful view!

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

    Casa vacanze nel Chianti il Granaio is located in Castellina in Chianti, just 27 miles from Pitti Palace and 28 miles from Strozzi Palace. 21 miles from Piazza Matteotti and 24 miles from Piazza del...

    Posto incantevole, meraviglioso! Proprietari super gentili

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

    Providing a garden, Salto di Gatto provides accommodations in Castellina in Chianti. This property offers access to a balcony, free private parking, and free Wifi.

    Geschmackvolle Einrichtung, einfach, aber sehr liebevoll!

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

    Featuring an infinity pool, Villetta Adelma Fioraie features accommodations in Castellina in Chianti. This property offers access to a terrace, free private parking, and free Wifi.

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

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

  • Villetta La Miniera
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 7 reviews

    Featuring a garden, Villetta La Miniera features accommodations in Castellina in Chianti. This property offers access to a terrace, free private parking, and free Wifi.

    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
    Excellent
    Rated excellent
     · 9 reviews

    Featuring a garden, Casa il Cipresso, in the heart of Chianti with swimming pool offers accommodations in Castellina in Chianti.

  • Holiday Home Cignanbianco - Tramonto by Interhome
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 8 reviews

    Holiday Home Cignanbianco - Tramonto by Interhome is located in Castellina in Chianti, just 17 miles from Piazza Matteotti and 31 miles from Pitti Palace.

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

  • Holiday Home Cellole - Valluccia by Interhome
    8.9
    Scored 8.9
    Excellent
    Rated excellent
     · 7 reviews

    Holiday Home Cellole - Valluccia by Interhome offers accommodations in Castellina in Chianti, 13 miles from Piazza Matteotti and 14 miles 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
    Wonderful
    Rated wonderful
     · 2 reviews

    Providing a garden, The House, Tuscany and the pool features accommodations in Castellina in Chianti. This property offers access to a terrace and free private parking.

  • Bellosguardo 8
    Budget options available

    Bellosguardo 8 is located in Castellina in Chianti, just 8.4 miles from Piazza del Campo and 18 miles from Piazza Matteotti.

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

    Featuring a garden, Casa Chianti Classico, Panoramic View - Happy Rentals offers accommodations in Castellina in Chianti.

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

    Il Villino Farmhouse is a recently renovated vacation home in Castellina in Chianti where guests can make the most of its garden and barbecue facilities.

Great access to the city center! Check these vacation homes in Castellina in Chianti

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

    Cottage San Bartolomeo is located in Castellina in Chianti, just 14 miles from Piazza Matteotti and 14 miles from Piazza del Campo.

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

    Providing a terrace, Casa Fioraie by PosarelliVillas provides accommodations in Castellina in Chianti. This property offers a private pool, free Wifi, and free private parking.

  • Bellosguardo
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Bellosguardo offers accommodations in Castellina in Chianti, 8.4 miles from Piazza del Campo and 18 miles from Piazza Matteotti.

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

    Featuring a garden, Casa Gosi provides accommodations in Castellina in Chianti. This property offers access to a balcony, free private parking, and free Wifi.

    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

    Holiday Home Cignanbianco - Alba by Interhome offers accommodations in Castellina in Chianti, 17 miles from Piazza Matteotti and 31 miles from Pitti Palace.

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

    Chianti Suite in Castellina in Chianti provides accommodations with an infinity pool, 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

    Holiday Home Casa Chiara by Interhome offers accommodations in Castellina in Chianti, 12 miles from Piazza Matteotti and 13 miles from Piazza del Campo.

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

    Casa Antico Roseto with swimming pool offers accommodations in Castellina in Chianti, 8.9 miles from Piazza Matteotti and 20 miles from Piazza del Campo.

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

    14 miles from Piazza Matteotti in Castellina in Chianti, Villa Delle Upupe 8, Emma Villas features accommodations with access to a solarium.

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

    Casa Belvedere cottage with swimming pool offers accommodations in Castellina in Chianti, 8.8 miles from Piazza Matteotti and 20 miles from Piazza del Campo.

  • Holiday Home Olivo by Interhome

    Holiday Home Olivo by Interhome is located in Castellina in Chianti, just 13 miles from Piazza Matteotti and 13 miles from Piazza del Campo.

  • Casanovina

    Casanovina is located in Castellina in Chianti, just 13 miles from Piazza Matteotti and 14 miles from Piazza del Campo. This property offers a private pool, free Wifi, and free private parking.

  • Casale Cipressi

    13 miles from Piazza Matteotti in Castellina in Chianti, Casale Cipressi features accommodations with access to an open-air bath.

  • Macia Viva

    Featuring a garden, Macia Viva offers accommodations in Castellina in Chianti. This property offers a private pool, free Wifi, and free private parking. Outdoor dining is also possible at the villa.

  • Casale Sandonatino by VacaVilla

    Casale Sandonatino by VacaVilla offers accommodations in Castellina in Chianti, 14 miles from Piazza Matteotti and 15 miles from Piazza del Campo.

  • Casale Cipressi

    Casale Cipressi is located in Castellina in Chianti, just 14 miles from Piazza Matteotti and 16 miles from Piazza del Campo.

  • Villa La Casina

    15 miles from Piazza Matteotti in Castellina in Chianti, Villa La Casina provides accommodations with access to a fitness center.

  • Villa Castellina - Homelilke Villas

    Villa Castellina - Homelilke Villas is located in Castellina in Chianti, just 12 miles from Piazza del Campo and 15 miles from Piazza Matteotti.

  • Ginestra

    Ginestra is located in Castellina in Chianti, just 16 miles from Piazza Matteotti and 17 miles from Piazza del Campo. Both free Wifi and parking on-site are available at the villa free of charge.

  • Antico Cipresso

    Antico Cipresso is located in Castellina in Chianti, just 8.6 miles from Piazza Matteotti and 19 miles from Piazza del Campo.

  • Casetta Erika

    Casetta Erika is located in Castellina in Chianti, just 17 miles from Piazza Matteotti and 18 miles from Piazza del Campo. This property offers a private pool, free Wifi, and free private parking.

  • 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

    Casa Anita - pool and tennis court Castellina in Chianti - Granaio, Toscana is located in Castellina in Chianti, just 27 miles from Pitti Palace and 28 miles from Strozzi Palace. 20 miles from Piazza...

FAQ about vacation homes in Castellina in Chianti





Vacation 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: £236.24
    8.8
    Scored 8.8
    Excellent
    Rated excellent
     · 851 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
  • Avg. price/night: £245.95
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 311 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
    Wonderful
    Rated wonderful
     · 272 reviews
    Very clean and comfy accomodation. Our landlord- Kristína was helpfull and entertaining. I highly recommend the place.
    Julka Fristikova
    Travelers with friends
  • 9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 662 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
    Wonderful
    Rated wonderful
     · 662 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
    Wonderful
    Rated wonderful
     · 27 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: £82.69
    7.8
    Scored 7.8
    Good
    Rated good
     · 406 reviews
    House was old and authentic but very clean and cozy.
    Darko
    Young couple
  • Avg. price/night: £130.61
    9.0
    Scored 9.0
    Wonderful
    Rated wonderful
     · 689 reviews
    So friendly. Lovely pool. Great location and very clean.
    Pieter
    Family with young children
gogless