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

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Top guest favourite
Cottage in Castellina in Chianti
Cappero Cottage - Masseto In Chianti
2 bedrooms, 3 beds, 2 private bathrooms
27 Sept – 2 Oct, Business host
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4.97 out of 5 average rating, 115 reviews
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Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
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
Individual host
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
Individual host
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
Business host
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
Business host
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
Individual host
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
Business host
3–8 Oct
5.0 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
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Castellina in Chianti
Two-bedroom apartment
Business host
5–10 Oct
4.8 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
24–29 Sept
4.96 out of 5 average rating, 245 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Top guest favourite
Home in Magliano
Alba in Chianti
Individual host
3–8 Oct
5.0 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
New place to stay
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Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
Business host
8–13 Oct
5.0 out of 5 average rating, 49 reviews
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Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
19–24 Sept
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Home in Castellina in Chianti
3 bedroom stone house on olive grove
Individual host
23–28 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 15 reviews