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

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Guest favourite
Cottage in Castellina in Chianti
Cottage in Chianti with a pool
3 bedrooms, 3 beds, 2.5 private bathrooms
3–8 Sept
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4.86 out of 5 average rating, 44 reviews
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Top guest favourite
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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Top guest favourite
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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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, 83 reviews
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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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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
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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
25–30 Oct
4.97 out of 5 average rating, 31 reviews
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Top guest favourite
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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Top guest favourite
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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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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Top guest favourite
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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Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds, 2 bathrooms
4–9 Sept
5.0 out of 5 average rating, 3 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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Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Home in Tregole
Romantic villa in the Chianti Classico
8 bedrooms, 9 beds, 8 bathrooms
12–17 Oct
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Top guest favourite
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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Flat in Certaldo
La Casa di Mario: Apt near Siena and Florence
3 bedrooms, 3 double beds, 1.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews