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Search results; Over 1,000 homes in Castellina Scalo

Photo 1 of 17
Top guest favourite
Apartment in Castellina Scalo
Above the Post Office
2 bedrooms, 3 beds, 1 bathroom
3–8 Dec
,
4.98 out of 5 average rating, 126 reviews
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Guest favourite
Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
1 bedroom, 2 beds, 1 bathroom
24–29 Sept
4.89 out of 5 average rating, 18 reviews
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Top guest favourite
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, 18 reviews
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Home in Castellina Scalo
Casa Serena Chianti - 5 min to Station
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
New place to stay
Photo 1 of 29
Top guest favourite
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, 135 reviews
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Top guest favourite
Flat in Gavignano
Poggio Massiccioli
2 bedrooms, 2 queen beds, 1 bathroom
30 Oct – 4 Nov
4.92 out of 5 average rating, 389 reviews
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Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 33 reviews
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Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Villa in Tignano
Villa Isabella
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 209 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, 87 reviews
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Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.96 out of 5 average rating, 149 reviews
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Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
3 bedrooms, 4 beds, 3 bathrooms
6–11 Oct
4.98 out of 5 average rating, 218 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
New place to stay
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 6 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
18–23 Sept
4.98 out of 5 average rating, 60 reviews
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.98 out of 5 average rating, 47 reviews
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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 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Castle in Poggibonsi
Castello Di Badia – Panoramic Pool Overlooking Tuscany
5 bedrooms, 6 beds, 5.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 72 reviews
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Top guest favourite
Villa in Monteriggioni
Tenuta Uzielli an elegant countryside villa
7 bedrooms, 7 beds, 8 bathrooms
1–6 May
5.0 out of 5 average rating, 20 reviews