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Search results; Over 1,000 homes in Castellina Scalo

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
Guest favourite
Apartment in Castellina Scalo
Da nonna Cri, apartment in Chianti
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.89 out of 5 average rating, 18 reviews
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
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 10 reviews
Flat in Pievescola
TuscanView 360: 3 bedr, 2 baths, free parking
3 bedrooms, 4 beds, 2 bathrooms
9–14 Oct
4.96 out of 5 average rating, 148 reviews
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
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
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, 86 reviews
Top guest favourite
Villa in Greve in Chianti
Medieval castle (27 beds)-Chianti-Florence 15km
8 bedrooms, 16 beds, 11.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 73 reviews
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
Top guest favourite
Cottage in Barberino Tavarnelle
Stone House with Exclusive Pool Codilungo in Chianti
3 bedrooms, 4 beds, 3 bathrooms
19–24 Oct
4.98 out of 5 average rating, 218 reviews
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, 33 reviews
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, 387 reviews
Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms, 2 beds, 1 bathroom
23–28 Sept
5.0 out of 5 average rating, 3 reviews
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
Top guest favourite
Farm stay in Poggibonsi
I Melograni del Chianti - Apt. Mangiatoia 2BR
2 bedrooms, 2 double beds, 1.5 bathrooms
16–21 Apr
4.95 out of 5 average rating, 22 reviews
Guest favourite
Townhouse in Colle di Val d'Elsa
L'Arco
3 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Apartment in Ponte a Bozzone
The tranquility of the Geggiano forest
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 22 reviews