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

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Top guest favourite
Home in Castellina in Chianti
Leonardo - Chianti/Siena, Florence, San Gimignano.
2 bedrooms, 3 beds, 1 private bathroom
24–29 Oct
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4.97 out of 5 average rating, 120 reviews
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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, 58 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, 98 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
27 Oct – 1 Nov
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
29 Oct – 3 Nov
4.98 out of 5 average rating, 89 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
5.0 out of 5 average rating, 4 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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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, 33 reviews
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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, 34 reviews
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Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
20–25 Oct
4.98 out of 5 average rating, 61 reviews
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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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Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds, 5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 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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Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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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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Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 57 reviews
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Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
7 bedrooms, 8 beds, 7 bathrooms
1–6 Oct
5.0 out of 5 average rating, 12 reviews
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Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 32 reviews
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Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 38 reviews