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

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Guest favourite
Holiday home in Castellina in Chianti
Cenerentola chianti 1 apartment - near Panzano
3 bedrooms, 5 beds, 3 private bathrooms
29 Sept – 4 Oct
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4.9 out of 5 average rating, 10 reviews
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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, 57 reviews
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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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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
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 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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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
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
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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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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
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms, 3 double beds
21–26 Sept
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Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds
8–13 Oct
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Flat in Castellina in Chianti
Two-bedroom apartment
2 bedrooms
5–10 Oct
4.8 out of 5 average rating, 10 reviews
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Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds
23–28 Sept
5.0 out of 5 average rating, 3 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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Home in Tregole
Romantic villa in the Chianti Classico
8 bedrooms, 9 beds
12–17 Oct
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Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds
17–22 Oct
5.0 out of 5 average rating, 38 reviews
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Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms, 4 beds
23–28 Oct
4.95 out of 5 average rating, 19 reviews