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

Top guest favourite
Cottage in Castellina in Chianti
Vittoria Cottage – Masseto in Chianti
2 bedrooms, 3 beds, 2 shared bathrooms
5–10 Oct
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4.96 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Sept
4.95 out of 5 average rating, 56 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 18 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
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
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 129 reviews
Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 32 reviews
Flat in Siena
Affaccio sulla valle: next to P.delCampo, wifi, ac
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
New place to stay
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 10 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, 81 reviews
Holiday home in Barberino Tavarnelle
Le Querciole di Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
27 Aug – 1 Sept
New place to stay
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds, 5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Magliano
Alba in Chianti
3 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 57 reviews
Superhost
Home in Greve in Chianti
Villa with a swimming pool in the heart of Chianti | Florence
3 bedrooms, 3 double beds, 3 bathrooms
27 Aug – 1 Sept
New place to stay
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds, 3 bathrooms
21–26 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Panzano in Chianti
Alessandro's apartment
1 bedroom, 1 queen bed, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 11 reviews