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

Guest favourite
Flat in Castellina in Chianti
La dolce vita in Chianti. Pool and Relaxation
2 bedrooms, 3 beds, 1 private bathroom
12–17 Sept
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4.85 out of 5 average rating, 347 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
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 54 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
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.99 out of 5 average rating, 465 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Home in Barberino Tavarnelle
Enjoy Amazing View in Tuscany in Our Country House
1 bedroom, 2 beds, 1 bathroom
20–25 Nov
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Apartment in Bivio Santo Stefano
Agriturismo Osea, Sunset flat
1 bedroom, 2 beds, 1 bathroom
5–10 Aug
4.99 out of 5 average rating, 147 reviews
Guest favourite
Apartment in San Gimignano
Casolare apartment with pool “Casa Monti”
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
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
Top guest favourite
Apartment in Ponte a Bozzone
The tranquility of the Geggiano forest
2 bedrooms, 3 beds, 2 bathrooms
7–12 Aug
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds, 5 bathrooms
12–17 Sept
Top guest favourite
Farm stay in Impruneta
"Nocino Apartment" - Farmhouse - Chianti
1 bedroom, 1 double bed, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 123 reviews
Home in Castel San Gimignano
Elegant private villa: Volterra–San Gimignano
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
New place to stay
Home in Radda in Chianti
Stunning villa for relaxation or intimate weddings
8 bedrooms, 8 beds, 8 bathrooms
15–20 Aug
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
16–21 Oct
Top guest favourite
Room in San Casciano In Val di Pesa
Independent loft in the heart of Chianti
2 beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 24 reviews