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Castellina in Chianti

Excellent 468 Reviews 4.8/5
A vacation rental in Castellina in Chianti within the Chianti tourist area in Tuscany is a great choice if you are planning to spend a holiday togeteher with family or friends in Italy. Browsing holiday rentals near Castellina in Chianti with guest reviews is a good way to start planning your trip. Unlike a typical hotel stay, or a common holiday rental, our vacation rentals in Castellina in Chianti are carefully selected to offer the best experience with all the comforts you expect for your stay. Also consider other vacation rentals nearby Castellina in Chianti as villas with pool in Castellina in Chianti, last minute rentals near Castellina in Chianti, apartments in Castellina in Chianti and luxury villas for rent in Castellina in Chianti. If you don’t find the right solution here we suggest you to expand your search to see our villas in Tuscany or all our holiday rentals in Italy.

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Results 16 - 30 of 34
  • 12
  • 48
  • 24
  • 20
  • Property in the center of Greve in Chianti
  • Perfect for Chianti Classico winetour
  • Table tennis and pool table
from 110 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.

Mercantino

 6  3  3
from169 $
per night

Panorama

 6  3  3
from169 $
per night

Frantoio

 6  3  3
from169 $
per night

Molino

 6  3  3
from169 $
per night

Iris

 4  2  1
from143 $
per night

Steccaia

 4  2  1
from143 $
per night

Borro

 4  2  1
from143 $
per night

Giaggiolo

 4  2  1
from143 $
per night

Gramola

 2  1  1  55 m2
from110 $
per night

Buratto

 2  1  1
from110 $
per night

Fiocchetto

 2  1  1
from110 $
per night

Caratello

 2  1  1
from110 $
per night
  • 4
  • 2
  • 1
  • 80 m2
  • View of the towers of San Gimignano
  • Surrounded by the Tuscan hills
  • Large garden
from 162 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
Someone else is currently looking at this property!
  • 6
  • 3
  • 3
  • 350 m2
  • Historical building dating back to the end of the 16th century
  • Fine interiors and panoramic views
  • Basic services within walking distance
from 317 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 10
  • 5
  • 2
  • 220 m2
  • Traditional Tuscan dwelling
  • Terrace with a panoramic view
  • Village of Lucolena within walking distance
from 285 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 16
  • 8
  • 8
  • 550 m2
  • Magnificent rustic villa with views of San Gimignano
  • 8 bedrooms and 8 bathrooms
  • Perfect to organize events
from 1633 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 15
  • 8
  • 7
  • 400 m2
  • Renovated villa of 17th century
  • Panoramic position in the Chianti area
  • Suitable for events
from 370 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 3
  • 18
  • 6
  • 6
  • Former barn completely renovated
  • Enchanting view of the Tuscan countryside
  • Excellent position to explore the area
from 104 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.

Glicini 1

 4  1  1  45 m2
from104 $
per night

Glicini 2

 6  2  2  80 m2
from187 $
per night

Glicini 3

 8  3  3  95 m2
from267 $
per night
  • 2
  • 1
  • 1
  • 50 m2
  • Old barn recently restored
  • Ideal for romantic getaways
  • Only 4 km far from Siena
from 170 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 4
  • 2
  • 3
  • 130 m2
  • Characteristic house in the Chianti hills
  • Terrace with shared pool
  • Excellent location for wine lovers
from 136 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 9
  • 5
  • 2
  • 335 m2
  • Traditional country villa in Chianti, Tuscany
  • Large indoor and outdoor spaces
  • Swimming pool overlooking the surrounding countryside
from 347 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 6
  • 30
  • 11
  • 10
  • Large rustic country property
  • Beautiful swimming pool with views over the Tuscan hills
  • Equipped panoramic terrace
from 103 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.

Tenuta 1

 4  1  1  68 m2
from103 $
per night

Tenuta 2

 4  1  1  66 m2
from103 $
per night

Tenuta 3

 4  2  2  66 m2
from135 $
per night

Tenuta 4

 2  1  1  45 m2
from103 $
per night

Tenuta 5

 6  2  2  82 m2
from140 $
per night

Tenuta 6

 10  4  3  125 m2
from208 $
per night
  • 12
  • 4
  • 4
  • 300 m2
  • Spacious Tuscan farmhouse in the heart of Chianti
  • Tennis/volleyball/basketball court
  • Basic services within walking distance
from 711 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 4
  • 2
  • 3
  • 130 m2
  • Charming house in the Chianti Classico hills
  • Terrace with shared pool
  • Excellent location for wine lovers
from 136 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 5
  • 2
  • 1
  • 130 m2
  • Beautiful property immersed in Chianti
  • Fine interior furnishings
  • Terrace with shared pool
from 130 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
  • 7
  • 4
  • 3
  • 140 m2
  • Beautiful villa with a panoramic view
  • Refined furnishings
  • Perfect for wine lovers (Chianti area)
from 293 $per night
Price of stay excluding taxes and extras. The final price will be calculated when you select your dates of stay.
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Guido Posarelli
Founder of Posarelli Villas, hand-picking all the vacation rentals in Italy we offer on our website.
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Cancellation Costs Cover

Included in the rental price! Our Commitment to a Worry-Free Experience.

We have introduced a cancellation penalty reimbursement mechanism, designed to provide our guests with an extra layer of security, allowing them to book with confidence.

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Special Deals

Looking for a memorable holiday experience without breaking the bank? With our range of advantageous deals and discount codes, you can enjoy incredible savings while creating unforgettable memories.

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Travel Experiences

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