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

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Guest favourite
Barn in Castellina in Chianti
Apartment T3
2 bedrooms, 2 beds, 2 private bathrooms
26–31 Oct
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4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
27 Oct – 1 Nov
4.95 out of 5 average rating, 57 reviews
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Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 98 reviews
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Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 reviews
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Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 33 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, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 15 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
New place to stay
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Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
5 bedrooms, 3 single beds, 3 bathrooms
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, 5 bathrooms
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, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.98 out of 5 average rating, 47 reviews
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Guest favourite
Flat in Castellina in Chianti
Two-bedroom apartment
2 bedrooms, 1 bathroom
5–10 Oct
4.8 out of 5 average rating, 10 reviews
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Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
18–23 Sept
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Top guest favourite
Flat in Barberino Val d'Elsa
Apartment in Chianti at Mulino dell'Argenna
1 bedroom, 1 double bed, 1 bathroom
17–22 Oct
4.99 out of 5 average rating, 153 reviews
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Home in Fonterutoli
Private house overlooking Siena
6 bedrooms, 10 beds, 6 bathrooms
2–7 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Apartment in Panzano in Chianti
Apt. Panzanello-Panzano in Chianti
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 281 reviews
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Flat in Castellina in Chianti
Apartment in the heart of Chianti
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
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Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds, 2 bathrooms
23–28 Sept
5.0 out of 5 average rating, 3 reviews