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

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Cottage in Castellina in Chianti
Cottage in Chianti with a pool
3 bedrooms, 3 beds, 2.5 private bathrooms
1–6 Sept
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4.86 out of 5 average rating, 44 reviews
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Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 56 reviews
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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, 97 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
5–10 Sept
New place to stay
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Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds, 5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 15 reviews
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Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 82 reviews
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Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 31 reviews
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Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 38 reviews
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Hut in Castellina in Chianti
Apartment in Chianti - Capanna
2 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.95 out of 5 average rating, 20 reviews
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Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
1–6 Sept
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Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 27 reviews
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Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 49 reviews
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Home in Tregole
Romantic villa in the Chianti Classico
8 bedrooms, 9 beds, 8 bathrooms
12–17 Sept
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Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Farm stay in Poggibonsi
Holiday home Poggio al olive trees
2 bedrooms, 4 beds, 3 bathrooms
16–21 Oct
5.0 out of 5 average rating, 32 reviews
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Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
2 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
4.96 out of 5 average rating, 244 reviews
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Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds, 1 bathroom
7–12 Oct
5.0 out of 5 average rating, 19 reviews