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Search results; Over 1,000 homes in Castellina Scalo

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Top guest favourite
Apartment in Castellina Scalo
Above the Post Office
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
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4.98 out of 5 average rating, 125 reviews
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Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.89 out of 5 average rating, 18 reviews
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Home in Castellina in Chianti
Capanna di Sotto by Interhome.
2 bedrooms, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 9 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 17 reviews
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Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 bedrooms, 2 beds, 2 bathrooms
30 Nov – 5 Dec
5.0 out of 5 average rating, 104 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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Home in Colle di Val d'Elsa
The House in the Alley – Colle di Val d'Elsa
2 bedrooms, 3 beds, 1 bathroom
5–10 Nov
4.99 out of 5 average rating, 133 reviews
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Home in Barberino Tavarnelle
Exclusive Villa with Pool in Chianti Classico
5 bedrooms, 5 double beds, 6 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
7 bedrooms, 7 beds, 8 bathrooms
7–12 Sept
5.0 out of 5 average rating, 20 reviews
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Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
3 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
4.98 out of 5 average rating, 215 reviews
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Apartment in Noce
Historic 17th-century farmhouse in Chianti, Tuscany
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 218 reviews
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Holiday home in Sovicille
Podere La Castellina - No. 6 ROSETO
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.99 out of 5 average rating, 82 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, 53 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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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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Villa in Impruneta
Private Estate - Personal Concierge & heated pool
6 bedrooms, 6 beds, 7 bathrooms
4–9 Oct
4.99 out of 5 average rating, 144 reviews
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Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 140 reviews
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Superhost
Barn in Castellina in Chianti
Cipressini 2 - pool and amazing views
1 bedroom, 2 beds, 1 bathroom
17–22 Nov
5.0 out of 5 average rating, 65 reviews