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

Top guest favourite
Home in Castellina in Chianti
Leonardo - Chianti/Siena, Florence, San Gimignano.
2 bedrooms, 3 beds, 1 private bathroom
12–19 Sept
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4.97 out of 5 average rating, 118 reviews
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
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
19–24 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
25–30 Oct
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
25–30 Oct
4.94 out of 5 average rating, 54 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, 45 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, 77 reviews
Guest favourite
Room in Castellina in Chianti
Mariani Bed & Breakfast, Double Room 2
1 double bed
18–23 Aug
5.0 out of 5 average rating, 12 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, 35 reviews
Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds
21–26 Aug
5.0 out of 5 average rating, 48 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds
19–24 Aug
Holiday home in Barberino Tavarnelle
Le Querciole di Mauro Corsi
4 bedrooms, 3 double beds
16–21 Aug
New place to stay
Superhost
Home in Greve in Chianti
Villa with a swimming pool in the heart of Chianti | Florence
3 bedrooms, 3 double beds
6–11 Sept
New place to stay
Superhost
Home in Castellina in Chianti
Small romantic apartment overlooking the vineyards
1 bedroom, 1 bed
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
10–15 Aug
5.0 out of 5 average rating, 129 reviews
Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
5 bedrooms, 3 single beds
15–22 Oct
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Home in Magliano
Alba in Chianti
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Nature lodge in Greve in Chianti
You will be the only guest Nature-Relax
1 bedroom, 1 double bed
11–16 Aug
4.93 out of 5 average rating, 221 reviews