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Search results; Over 1,000 homes in Castellina in Chianti

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Home in Castellina in Chianti
Casa Pineta - Authentic 4BR/4BA Farmhouse
4 bedrooms, 9 beds, 4 private bathrooms
24–31 Oct
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Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds
3–8 Oct
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 15 reviews
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Home in Fonterutoli
Private house overlooking Siena
6 bedrooms, 10 beds
2–7 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds
27 Oct – 1 Nov
4.95 out of 5 average rating, 58 reviews
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Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds
2–7 Nov
5.0 out of 5 average rating, 98 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds
20–25 Oct
4.98 out of 5 average rating, 61 reviews
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Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
5 bedrooms, 3 single beds
15–22 Oct
4.75 out of 5 average rating, 4 reviews
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Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Villa in Lilliano
Panoramic villa with pool and airco by Vacavilla
5 bedrooms, 6 beds
21–28 Oct
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Guest favourite
Villa in Gaiole in Chianti
Casa Faraona, villa with private pool
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds
25–30 Oct
4.97 out of 5 average rating, 33 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds
29 Oct – 3 Nov
4.98 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
3 bedrooms, 3 double beds
27 Oct – 1 Nov
4.99 out of 5 average rating, 115 reviews
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
3 bedrooms, 3 beds
17–24 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds
20–25 Oct
5.0 out of 5 average rating, 143 reviews