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

Top guest favourite
Home in Castellina in Chianti
Explore Chianti from a Charming Stone House
2 bedrooms, 2 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.98 out of 5 average rating, 121 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
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds, 1 bathroom
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, 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
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
Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
Superhost
Home in Greve in Chianti
Villa with a swimming pool in the heart of Chianti | Florence
3 bedrooms, 3 double beds, 3 bathrooms
6–11 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
Holiday home in Barberino Tavarnelle
Le Querciole di Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
1–6 Sept
New place to stay
Superhost
Flat in Poggibonsi
Il Casale di Villore, Poggibonsi, Siena, Tuscany, Prugnolo Apt.
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Panzano in Chianti
Alessandro's apartment
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 11 reviews
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Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 37 reviews
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Flat in Radda in Chianti
Heart of Chianti - a warm flat in Radda
1 bedroom, 1 king bed, 1 bathroom
5–10 Sept
4.92 out of 5 average rating, 123 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
Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
5 bedrooms, 3 single beds, 3 bathrooms
15–22 Oct
4.75 out of 5 average rating, 4 reviews
Room in Barberino Val d'Elsa
Compact Double | Chianti | Pool & Restaurant
1 double bed, 1 bathroom
27 Sept – 2 Oct
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 25 reviews