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

Guest favourite
Flat in Castellina in Chianti
Apartment T4
2 bedrooms, 2 beds, 2 private bathrooms
28 Oct – 2 Nov
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4.87 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds
25–30 Oct
4.95 out of 5 average rating, 56 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 Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds
29 Oct – 3 Nov
4.98 out of 5 average rating, 84 reviews
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds
18–23 Oct
5.0 out of 5 average rating, 15 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds
15–20 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
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, 31 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds
3–8 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds
2–7 Nov
5.0 out of 5 average rating, 27 reviews
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms, 3 double beds
3–8 Sept
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
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds
19–24 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
2 bedrooms, 4 beds
16–21 Sept
4.96 out of 5 average rating, 244 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 9 reviews
Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Panzano in Chianti
Alessandro's apartment
1 bedroom, 1 queen bed
4–9 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds
26–31 Oct
4.99 out of 5 average rating, 69 reviews
Flat in Certaldo
La Casa di Mario: Apt near Siena and Florence
3 bedrooms, 3 double beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 4 reviews