filters

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

Photo 1 of 6
Top guest favourite
Apartment in Castellina in Chianti
Il Giaggiolo – Chianti with a view
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
,
4.97 out of 5 average rating, 62 reviews
Photo 1 of 6
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 56 reviews
Photo 1 of 6
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
Photo 1 of 6
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
1–6 Sept
New place to stay
Photo 1 of 6
Home in Castellina in Chianti
3 bedroom stone house on olive grove
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 6
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
Photo 1 of 6
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, 31 reviews
Photo 1 of 6
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
Photo 1 of 6
Top guest favourite
Hut in Castellina in Chianti
Apartment in Chianti - Capanna
2 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.95 out of 5 average rating, 20 reviews
Photo 1 of 6
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 82 reviews
Photo 1 of 6
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 38 reviews
Photo 1 of 6
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
1–6 Sept
New place to stay
Photo 1 of 6
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
6 bedrooms, 7 beds, 6.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 60 reviews
Photo 1 of 6
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
Photo 1 of 6
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 26 reviews
Photo 1 of 6
Home in Tregole
Romantic villa in the Chianti Classico
8 bedrooms, 9 beds, 8 bathrooms
12–17 Sept
Photo 1 of 6
Top guest favourite
Flat in Monteriggioni
Osea Agritourism, Alba apartment
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 49 reviews
Photo 1 of 6
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 12 reviews
Photo 1 of 6
Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
New place to stay