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

Top guest favourite
Cottage in Castellina in Chianti
Vittoria Cottage – Masseto in Chianti
2 bedrooms, 3 beds, 2 shared bathrooms
5–10 Oct
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4.96 out of 5 average rating, 114 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 30 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 Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds
3–8 Sept
4.95 out of 5 average rating, 56 reviews
Holiday home in Barberino Tavarnelle
Le Querciole di Mauro Corsi
4 bedrooms, 3 double beds
1–6 Sept
New place to stay
Top guest favourite
Villa in Noce
Historic villa with private pool in Tuscany
2 bedrooms, 4 beds
11–16 Nov
5.0 out of 5 average rating, 35 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds
8–13 Oct
5.0 out of 5 average rating, 26 reviews
Rooms in Barberino Val d'Elsa
Four-Poster Bed | Agriturismo with Pool | Chianti
2 bedrooms, 2 beds
30 Sept – 5 Oct
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds
7–12 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
2–7 Sept
4.96 out of 5 average rating, 242 reviews
Room in Barberino Val d'Elsa
Compact Double | Chianti | Pool & Restaurant
1 double bed
27 Sept – 2 Oct
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds
8–13 Oct
5.0 out of 5 average rating, 12 reviews
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
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, 68 reviews
Top guest favourite
Room in San Casciano In Val di Pesa
Independent loft in the heart of Chianti
2 beds
4–9 Oct
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
3 bedrooms, 4 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Farm stay in Impruneta
"Nocino Apartment" - Farmhouse - Chianti
1 bedroom, 1 double bed
4–9 Oct
5.0 out of 5 average rating, 125 reviews