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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, 114 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, 56 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds
7–12 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds
2–7 Nov
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
1 bedroom, 1 double bed
6–11 Oct
5.0 out of 5 average rating, 129 reviews
Top guest favourite
Flat in Panzano in Chianti
Alessandro's apartment
1 bedroom, 1 queen bed
1–6 Sept
5.0 out of 5 average rating, 11 reviews
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
Flat in Poggibonsi
Il Casale di Villore, Poggibonsi, Siena, Tuscany, Prugnolo Apt.
1 bedroom, 1 queen bed
26 Sept – 1 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 37 reviews
Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Holiday home in Barberino Tavarnelle
Le Querciole di Mauro Corsi
4 bedrooms, 3 double beds
1–6 Sept
New place to stay
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
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
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
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed
16–21 Oct
5.0 out of 5 average rating, 3 reviews
Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms, 2 beds
1–6 Sept
New place to stay
Room in Barberino Val d'Elsa
Compact Double | Chianti | Pool & Restaurant
1 double bed
27 Sept – 2 Oct
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds
8–13 Oct
5.0 out of 5 average rating, 25 reviews