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

Superhost
Home in Castellina in Chianti
The House , Tuscany and the pool
3 bedrooms, 3 beds, 3 private bathrooms
27 Oct – 1 Nov
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4.71 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
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
Individual host
2–7 Nov
5.0 out of 5 average rating, 97 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, 31 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
4–9 Oct
5.0 out of 5 average rating, 3 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, 84 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
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
Flat in Monteriggioni
Osea Agritourism, Alba apartment
Business host
13–18 Sept
5.0 out of 5 average rating, 49 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
Home in Poggibonsi
Relax in Chianti countryside
Individual host
3–8 Sept
5.0 out of 5 average rating, 38 reviews
Home in Castellina in Chianti
3 bedroom stone house on olive grove
Individual host
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Castellina in Chianti
Two-bedroom apartment
Business host
17–22 Oct
4.8 out of 5 average rating, 10 reviews
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
Individual host
16–21 Oct
5.0 out of 5 average rating, 12 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
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
Top guest favourite
Home in Magliano
Alba in Chianti
Individual host
30 Oct – 4 Nov
5.0 out of 5 average rating, 59 reviews