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Villas Castellina in Chianti to rent

We have 21 properties to choose from.
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Farmhouse Castellina in Chianti
70 m² farmhouse ∙ 4 guests ∙ 2 bedrooms

Farmhouse Cerretino Vigna

Castellina in Chianti, Province of Siena, Italy
from £111
per night
4.8
Outstanding
(6 ratings)
from £111
per night
View deal
Apartment Castellina in Chianti
100 m² apartment ∙ 6 guests ∙ 3 bedrooms

Apartment La Foresta

Castellina in Chianti, Province of Siena, Italy
from £149
per night
from £149
per night
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Farmhouse Castellina in Chianti
180 m² farmhouse ∙ 14 guests ∙ 7 bedrooms

Farmhouse Cerretino group house 14 sleeps

Castellina in Chianti, Province of Siena, Italy
from £436
per night
from £436
per night
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Farmhouse Castellina in Chianti
267 m² farmhouse ∙ 12 guests ∙ 6 bedrooms

Farmhouse Podere Gioia

Castellina in Chianti, Province of Siena, Italy
from £276
per night
4.9
Outstanding
(34 ratings)
from £276
per night
View deal
Farmhouse Castellina in Chianti
130 m² farmhouse ∙ 9 guests ∙ 5 bedrooms

Farmhouse Cignanbianco - Alba e Tramonto

Castellina in Chianti, Province of Siena, Italy
from £139
per night
4.7
Excellent
(17 ratings)
from £139
per night
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Farmhouse Castellina in Chianti
314 m² farmhouse ∙ 16 guests ∙ 7 bedrooms

Farmhouse Casale Il Poggino

Castellina in Chianti, Province of Siena, Italy
from £617
per night
4.6
Excellent
(21 ratings)
from £617
per night
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Farmhouse Castellina in Chianti
60 m² farmhouse ∙ 4 guests ∙ 2 bedrooms

Farmhouse Cerretino Tettoia

Castellina in Chianti, Province of Siena, Italy
from £110
per night
4.6
Excellent
(8 ratings)
from £110
per night
View deal
House Castellina in Chianti
150 m² house ∙ 10 guests ∙ 4 bedrooms

House Terrazza sul Chianti

Castellina in Chianti, Province of Siena, Italy
from £224
per night
from £224
per night
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House Castellina in Chianti
50 m² house ∙ 4 guests ∙ 2 bedrooms

House Casa Patrizia

Castellina in Chianti, Province of Siena, Italy
from £62
per night
4.4
Very good
(12 ratings)
from £62
per night
View deal
Farmhouse Castellina in Chianti
80 m² farmhouse ∙ 4 guests ∙ 2 bedrooms

Farmhouse Olivo

Castellina in Chianti, Province of Siena, Italy
from £156
per night
4.2
Very good
(6 ratings)
from £156
per night
View deal
Apartment Castellina in Chianti
60 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment La Foresta

Castellina in Chianti, Province of Siena, Italy
from £106
per night
from £106
per night
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Apartment Castellina in Chianti
55 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment La Foresta

Castellina in Chianti, Province of Siena, Italy
from £95
per night
from £95
per night
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Apartment Castellina in Chianti
30 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment La Foresta

Castellina in Chianti, Province of Siena, Italy
from £86
per night
from £86
per night
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House Castellina in Chianti
75 m² house ∙ 4 guests ∙ 2 bedrooms

House Casa Chiara

Castellina in Chianti, Province of Siena, Italy
from £68
per night
4.5
Excellent
(22 ratings)
from £68
per night
View deal
Farmhouse Castellina in Chianti
120 m² farmhouse ∙ 6 guests ∙ 2 bedrooms

Farmhouse Olimpia

Castellina in Chianti, Province of Siena, Italy
from £221
per night
from £221
per night
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Farmhouse Castellina in Chianti
310 m² farmhouse ∙ 23 guests ∙ 9 bedrooms

Farmhouse Fattoria Petraglia

Castellina in Chianti, Province of Siena, Italy
from £444
per night
from £444
per night
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Farmhouse Castellina in Chianti
120 m² farmhouse ∙ 6 guests ∙ 2 bedrooms

Farmhouse Il Vallone

Castellina in Chianti, Province of Siena, Italy
from £128
per night
4.7
Excellent
(54 ratings)
from £128
per night
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Farmhouse Castellina in Chianti
107 m² farmhouse ∙ 6 guests ∙ 3 bedrooms

Farmhouse Cerretino Oliveto

Castellina in Chianti, Province of Siena, Italy
from £134
per night
5.0
Outstanding
(2 ratings)
from £134
per night
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Farmhouse Castellina in Chianti
190 m² farmhouse ∙ 8 guests ∙ 4 bedrooms

Farmhouse Podere San Lorenzo

Castellina in Chianti, Province of Siena, Italy
from £232
per night
4.7
Excellent
(37 ratings)
from £232
per night
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House Castellina in Chianti
150 m² house ∙ 8 guests ∙ 4 bedrooms

House Campiglia

Castellina in Chianti, Province of Siena, Italy
from £211
per night
4.4
Very good
(60 ratings)
from £211
per night
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House Castellina in Chianti
470 m² house ∙ 20 guests ∙ 10 bedrooms

House Borgo Castagnoli

Castellina in Chianti, Province of Siena, Italy
from £316
per night
4.6
Excellent
(24 ratings)
from £316
per night
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Apartment Castellina in Chianti
30 m² apartment ∙ 2 guests ∙ 1 bedroom

Apartment Podere Fontemaggio - Monolocale

Castellina in Chianti, Province of Siena, Italy
from £118
per night
4.7
Excellent
(28 ratings)
from £118
per night
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Farmhouse Castellina in Chianti
55 m² farmhouse ∙ 4 guests ∙ 1 bedroom

Farmhouse Il Poderino

Castellina in Chianti, Province of Siena, Italy
from £65
per night
4.0
Very good
(23 ratings)
from £65
per night
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Farmhouse Castellina in Chianti
80 m² farmhouse ∙ 6 guests ∙ 2 bedrooms

Farmhouse Il Sorriso

Castellina in Chianti, Province of Siena, Italy
from £124
per night
5.0
Outstanding
(26 ratings)
from £124
per night
View deal
Farmhouse Castellina in Chianti
140 m² farmhouse ∙ 5 guests ∙ 2 bedrooms

Farmhouse Decameron house

Castellina in Chianti, Province of Siena, Italy
from £152
per night
3.8
Good
(13 ratings)
from £152
per night
View deal
Apartment Castellina in Chianti
70 m² apartment ∙ 6 guests ∙ 2 bedrooms

Apartment Tipologia Trilo

Castellina in Chianti, Province of Siena, Italy
from £90
per night
4.5
Excellent
(4 ratings)
from £90
per night
View deal
House Castellina in Chianti
300 m² house ∙ 11 guests ∙ 6 bedrooms

House Lamore di Carla

Castellina in Chianti, Province of Siena, Italy
from £612
per night
5.0
Outstanding
(2 ratings)
from £612
per night
View deal
House Castellina in Chianti
100 m² house ∙ 8 guests ∙ 3 bedrooms

House Sissi

Castellina in Chianti, Province of Siena, Italy
from £201
per night
4.5
Excellent
(40 ratings)
from £201
per night
View deal
House Castellina in Chianti
160 m² house ∙ 12 guests ∙ 6 bedrooms

House Il Poggio

Castellina in Chianti, Province of Siena, Italy
from £263
per night
from £263
per night
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Apartment Castellina in Chianti
85 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment La Tinaia

Castellina in Chianti, Province of Siena, Italy
from £90
per night
4.8
Outstanding
(73 ratings)
from £90
per night
View deal
Apartment Castellina in Chianti
180 m² apartment ∙ 16 guests ∙ 7 bedrooms

Apartment Il Gufo n°1

Castellina in Chianti, Province of Siena, Italy
from £249
per night
4.1
Very good
(37 ratings)
from £249
per night
View deal
Apartment Castellina in Chianti
100 m² apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Padronale

Castellina in Chianti, Province of Siena, Italy
from £115
per night
3.5
Good
(2 ratings)
from £115
per night
View deal
House Castellina in Chianti
60 m² house ∙ 4 guests ∙ 2 bedrooms

House L'Oliviera

Castellina in Chianti, Province of Siena, Italy
from £74
per night
5.0
Outstanding
(19 ratings)
from £74
per night
View deal
Farmhouse Castellina in Chianti
260 m² farmhouse ∙ 10 guests ∙ 5 bedrooms

Farmhouse Vedi Torre

Castellina in Chianti, Province of Siena, Italy
from £380
per night
4.7
Excellent
(42 ratings)
from £380
per night
View deal
Holiday park Castellina in Chianti
116 m² holiday park ∙ 8 guests ∙ 3 bedrooms

Holiday park La Corte

Castellina in Chianti, Province of Siena, Italy
from £146
per night
4.6
Excellent
(73 ratings)
from £146
per night
View deal
House Castellina in Chianti
70 m² house ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

Castellina in Chianti, Province of Siena, Italy
from £58
per night
4.4
Very good
(21 ratings)
from £58
per night
View deal
House Castellina in Chianti
95 m² house ∙ 6 guests ∙ 3 bedrooms

House Lucolena

Castellina in Chianti, Province of Siena, Italy
from £117
per night
4.7
Excellent
(65 ratings)
from £117
per night
View deal
House Castellina in Chianti
110 m² house ∙ 5 guests ∙ 3 bedrooms

House Albachiara

Castellina in Chianti, Province of Siena, Italy
from £124
per night
from £124
per night
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Farmhouse Castellina in Chianti
40 m² farmhouse ∙ 4 guests ∙ 2 bedrooms

Farmhouse Badia a Passignano

Castellina in Chianti, Province of Siena, Italy
from £66
per night
4.3
Very good
(18 ratings)
from £66
per night
View deal
Farmhouse Castellina in Chianti
180 m² farmhouse ∙ 10 guests ∙ 5 bedrooms

Farmhouse Le Bonatte

Castellina in Chianti, Province of Siena, Italy
from £211
per night
4.9
Outstanding
(53 ratings)
from £211
per night
View deal

Customer reviews in Castellina in Chianti

Based on 6 ratings

The property has a stunning 360 degree view. The house was clean and the pool was wonderful for the hot summer. The property is walkable to the town (up a hill though). Castellina di Chianti is a beautiful small town with plenty of shopping and restaurants.

Candace

Reviewed on 15/08/2025

The place is very nice and works for a large group of people. We were unable to use the pool as it was too cold, but it was clean and exactly as shown in the photograph. The main road to and from the villa is filled with potholes so do not get a car low to the ground (this is no fault of the owners). Owner was very helpful and quick to respond to questions or concerns.

Matthew

Reviewed on 22/10/2024

Great Toscany Excellent location to visit Sienna and Florence

Danielle

Reviewed on 05/10/2024

Casa Chiara is a comfortable holiday home with a lot of privacy close to the old city center of Castellina with its many restaurants and shops. Also a nice starting point for bike rides and long walks. It has recently been upgraded. When the second bedroom has been updated and the bath has been replaced by a walk-in shower it will be excellent!

Ronald

Reviewed on 16/06/2024

We stayed during late September and the weather was not always kind to us (cold, rainy). However, we loved being so close to the village and it's many restaurants. The facilities were good but could do with a little face-lift and refit. For example, we found an ironing board but no iron (not a problem for us really) and the kitchen tap had become very wobbly. The host was very friendly and being able to chat with him via WhatsApp proved useful several times.

Phill

Reviewed on 04/10/2022

Once more an excellent stay in Cellole! Everything was perfect. Thank you very much!

Alex

Reviewed on 23/08/2021

Very nice apartment, swimming pool every day cleaned, also the area around the house, nice family, the owners with perfectly english opportunity to buy tuscany oil of olives, eggs & good wine We recommend and surely come back

Krzysztof

Reviewed on 10/11/2020

Top-Rated Lettings and Properties in Castellina in Chianti

Book Holiday Letting Offers with the Highest User Rating

Farmhouse Castellina in Chianti
from £90 per night
Farmhouse ∙ 4 guests ∙ 2 bedrooms

Farmhouse Capanna di Sopra

4.6
Excellent(50 ratings)
Castellina in Chianti, Province of Siena, Italy
View deal

Holiday homes with parking

Experience hassle-free arrivals and departures with our holiday homes in Castellina in Chianti offering convenient parking access for your convenience.

Apartment  Castellina in Chianti
from £76 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment Ciliegio

4.9
Outstanding(67 ratings)
Castellina in Chianti, Province of Siena, Italy
View deal
Farmhouse  Castellina in Chianti
from £45 per night
Farmhouse ∙ 4 guests ∙ 1 bedroom

Farmhouse Giuggiolo - Giuggiolo 3

4.5
Excellent(49 ratings)
Castellina in Chianti, Province of Siena, Italy
View deal
House  Castellina in Chianti
from £58 per night
House ∙ 6 guests ∙ 2 bedrooms

House Montechioccioli

4.5
Excellent(17 ratings)
Castellina in Chianti, Province of Siena, Italy
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Cool comfort: accommodation with refreshing air-conditioning in Castellina in Chianti

Enjoy cool comfort in our holiday homes in Castellina in Chianti equipped with refreshing air conditioning for ultimate relaxation.

House  Castellina in Chianti
from £210 per night
House ∙ 12 guests ∙ 6 bedrooms

House Ridaldi

Castellina in Chianti, Province of Siena, Italy
Air conditioning
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House  Castellina in Chianti
from £266 per night
House ∙ 5 guests ∙ 2 bedrooms

House Casa Padronale

Castellina in Chianti, Province of Siena, Italy
Air conditioning
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House  Castellina in Chianti
from £149 per night
House ∙ 6 guests ∙ 3 bedrooms

House Villa Francesca

3.8
Good(6 ratings)
Castellina in Chianti, Province of Siena, Italy
Air conditioning
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Best holiday lettings with a pool

A swimming pool is a holiday home staple, and with 90% of the holiday rentals in Castellina in Chianti providing pool access, there are plenty of great options from which to choose. Get ready to take a dip and dive into the top offers for accommodation with private pools in Castellina in Chianti.

Farmhouse  Castellina in Chianti
from £45 per night
Farmhouse ∙ 4 guests ∙ 1 bedroom

Farmhouse Giuggiolo - Giuggioli 1

4.5
Excellent(81 ratings)
Castellina in Chianti, Province of Siena, Italy
Pool
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Apartment  Castellina in Chianti
from £70 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment Badia a Passignano

4.1
Very good(52 ratings)
Castellina in Chianti, Province of Siena, Italy
Pool
View deal
Apartment  Castellina in Chianti
from £74 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Apartment Campiglia

4.4
Very good(38 ratings)
Castellina in Chianti, Province of Siena, Italy
Pool
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Holiday houses and apartments in:

Discover Castellina in Chianti

From your villa in Castellina in Chianti, you are treated to a magnificent panoramic view of the picturesque region, thanks to the elevated location. The villas, often featuring charming stone walls, are perfect for exploring the surrounding vineyards or taking a leisurely excursion to the La Rocca fortress.

Castellina in Chianti - Best Attractions

Tumulus of Montecalvario

Tumulus of Montecalvario

The Etruscan shaft tomb Tumulo di Montecalvario near Castellina in Chianti dates back to the 7th century BC and has four entrances pointing in all cardinal directions. The burial chambers, once guarded by a stone lion, are open for viewing.

Town Square

Town Square

The Piazza del Comune in Castellina in Chianti is the central square of the town, surrounded by charming medieval buildings. On this picturesque square, visitors can enjoy the atmosphere of Tuscan village life.

Archaeological Museum of the Chianti Senese

Archaeological Museum of the Chianti Senese

The exhibition of the Archaeological Museum focuses primarily on the ancient history of Castellina in Chianti and the neighboring places. Ancient war artifacts, ornate amphorae, bronze figures, sculptures, and much more take you on a journey through the past.

Church of the Holy Savior

Church of the Holy Savior

The plans for the newly built church San Salvadore in Castellina in Chianti were designed by the architect Menotti Lucattelli. Among the remarkable art treasures inside is a free-standing fresco by Maestro di Signa. The painting was created in the 15th century.

Street of the Arches

Street of the Arches

During bitter battles between Florence and Siena in the 13th century, Castellina in Chianti was destroyed several times, but was always rebuilt and equipped with stronger defensive walls. Beneath these, the underground tunnel Via delle Volte runs around the historic center.

Hand-picked and tested accommodation

Quality is our number one priority

Every property is checked before your arrival to ensure the best possible stay.

In-resort service and a 24/7 helpline

Make the most of our experience

Key collection is arranged by our helpful staff. Available 24/7 or on-site service to help you with all your questions, e.g.: tips and insights for your holiday destination and your booked accommodation.

A memorable holiday experience

Privacy and freedom in your own holiday homes

Be your own boss, eat whenever you want and make the most of plenty of space for all your friends and family.

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