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

Guest favourite
Flat in Castellina in Chianti
La dolce vita in Chianti. Swimming pool and relaxation
2 bedrooms, 3 beds, 1 private bathroom
8–13 Oct, Individual host
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4.85 out of 5 average rating, 351 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
26–31 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
Individual host
2–7 Nov
5.0 out of 5 average rating, 97 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
14–19 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
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 85 reviews
Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
Business host
15–22 Oct
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
Business host
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Flat in Castellina in Chianti
Two-bedroom apartment
Business host
5–10 Oct
4.8 out of 5 average rating, 10 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Home in Castellina in Chianti
3 bedroom stone house on olive grove
Individual host
10–15 Sept
5.0 out of 5 average rating, 3 reviews
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
8–13 Sept
Home in Tregole
Romantic villa in the Chianti Classico
Business host
12–17 Oct
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
Business host
18–23 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
Individual host
2–7 Nov
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
17–22 Oct
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
16–21 Sept
4.96 out of 5 average rating, 244 reviews
Home in Fonterutoli
Private house overlooking Siena
Individual host
2–7 Nov
5.0 out of 5 average rating, 3 reviews