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

Top guest favourite
Cottage in Castellina in Chianti
Cappero Cottage - Masseto In Chianti
2 bedrooms, 3 beds, 2 private bathrooms
23–28 Aug
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4.97 out of 5 average rating, 113 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds
22–29 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds
21–26 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds
3–8 Sept
4.95 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds
10–15 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds
25–30 Oct
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Castellina in Chianti
Visit Chianti, Florence, Siena, San Gimignano
2 bedrooms, 2 double beds
18–23 Mar
4.97 out of 5 average rating, 138 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds
4–9 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Castellina in Chianti
Mariani Bed & Breakfast, Double Room 2
1 double bed
1–6 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds
29 Oct – 3 Nov
4.97 out of 5 average rating, 78 reviews
Holiday home in Barberino Tavarnelle
Le Querciole di Mauro Corsi
4 bedrooms, 3 double beds
18–23 Aug
New place to stay
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds
24–29 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds
21–26 Aug
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed
18–23 Aug
5.0 out of 5 average rating, 129 reviews
Superhost
Home in Greve in Chianti
Villa with a swimming pool in the heart of Chianti | Florence
3 bedrooms, 3 double beds
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
18–23 Aug
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 reviews
Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 5 beds
23–28 Aug