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

Top guest favourite
Barn in Castellina in Chianti
Cipressini 2 - pool and amazing views
1 bedroom, 2 beds, 1 private bathroom
17–22 Nov
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5.0 out of 5 average rating, 64 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
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
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 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, 78 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
6 bedrooms, 8 beds
19–24 Aug
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed
13–18 Aug
5.0 out of 5 average rating, 129 reviews
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
27 Aug – 1 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
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds
1–6 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in San Donato
My home
2 bedrooms, 2 double beds
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Radda in Chianti
Heart of Chianti - a warm flat in Radda
1 bedroom, 1 king bed
19–24 Aug
4.92 out of 5 average rating, 123 reviews
Home in Castel San Gimignano
Elegant private cottage Volterra–San Gimignano
1 bedroom, 2 beds
12–17 Oct
New place to stay
Flat in Certaldo
La Casa di Mario: Apt near San Gimignano
3 bedrooms, 3 double beds
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Greve in Chianti
BorgoHome, apartment in downtown Greve in Chianti
2 bedrooms, 2 double beds
15–20 Aug
4.94 out of 5 average rating, 52 reviews