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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
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
30 Sept – 5 Oct
5.0 out of 5 average rating, 9 reviews
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Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds
10–17 Oct
5.0 out of 5 average rating, 17 reviews
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Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
7 bedrooms, 7 beds
7–12 Sept
5.0 out of 5 average rating, 20 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
5–10 Nov
4.99 out of 5 average rating, 133 reviews
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Flat in Castellina in Chianti
Relax in Chianti
1 bedroom, 2 beds
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
3 bedrooms, 4 beds
1–6 Sept
4.96 out of 5 average rating, 148 reviews
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Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds
1–6 Sept
4.98 out of 5 average rating, 60 reviews
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Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 49 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
5–10 Sept
New place to stay
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Top guest favourite
Apartment in Monteriggioni
Loggiato di Lorena - Along the Via Francigena
2 bedrooms, 2 double beds
4–9 Sept
4.95 out of 5 average rating, 19 reviews
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Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
3 bedrooms, 4 beds
7–12 Sept
4.98 out of 5 average rating, 215 reviews
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Room in Monteriggioni
Rooms and Wine Monteriggioni, I giardini
2 beds
24–29 Oct
4.95 out of 5 average rating, 22 reviews
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Home in Castel San Gimignano
Elegant private cottage Volterra–San Gimignano
1 bedroom, 2 beds
10–15 Nov
5.0 out of 5 average rating, 3 reviews
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Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 bedrooms, 2 beds
30 Nov – 5 Dec
5.0 out of 5 average rating, 104 reviews
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Villa in Greve in Chianti
Medieval castle (27 beds)-Chianti-Florence 15km
8 bedrooms, 16 beds
7–12 Sept
4.99 out of 5 average rating, 73 reviews
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Superhost
Townhouse in Quartaia
Casa Lida [Garden+Parking]
2 bedrooms, 2 beds
1–6 Sept
5.0 out of 5 average rating, 83 reviews
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Townhouse in Colle di Val d'Elsa
L'Arco
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 5 reviews