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

Top guest favourite
Villa in Castellina in Chianti
Manor House - IlVillinoFarmhouse
4 bedrooms, 5 beds, 2 private bathrooms
23–28 Oct
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4.93 out of 5 average rating, 253 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Aug
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds, 1 bathroom
6–11 Aug
5.0 out of 5 average rating, 17 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, 30 reviews
Superhost
Home in Castellina in Chianti
Small romantic apartment overlooking the vineyards
1 bedroom, 1 bed, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 128 reviews
Top guest favourite
Flat in San Donato
Loft in the heart of Chianti.
1 bedroom, 1 double bed, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 116 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds, 5 bathrooms
12–17 Sept
Superhost
Home in Greve in Chianti
Villa with a swimming pool in the heart of Chianti | Florence
3 bedrooms, 3 double beds, 3 bathrooms
6–11 Sept
New place to stay
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
20–25 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Barberino Tavarnelle
Infinity pool in Chianti area
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 135 reviews
Top guest favourite
Apartment in Bivio Santo Stefano
Agriturismo Osea, Sunset flat
1 bedroom, 2 beds, 1 bathroom
3–8 Aug
4.99 out of 5 average rating, 147 reviews
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
24–29 Aug
5.0 out of 5 average rating, 18 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
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Barberino Val d'Elsa
Apartment in Chianti at Mulino dell'Argenna
1 bedroom, 1 double bed, 1 bathroom
12–19 Sept
4.99 out of 5 average rating, 148 reviews
Top guest favourite
Flat in San Donato
My home
2 bedrooms, 2 double beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Farm stay in Greve in Chianti
Ancient Tuscan farmhouse in the Chianti hills
2 bedrooms, 2 double beds, 1 bathroom
9–14 Nov
4.99 out of 5 average rating, 280 reviews