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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
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
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
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, 4 bathrooms
1–6 Sept
New place to stay
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Rooms in Barberino Val d'Elsa
Four-Poster Bed | Agriturismo with Pool | Chianti
2 bedrooms, 2 beds, 1 bathroom
30 Sept – 5 Oct
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds, 1 bathroom
7–12 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 25 reviews
Room in Barberino Val d'Elsa
Compact Double | Chianti | Pool & Restaurant
1 double bed, 1 bathroom
27 Sept – 2 Oct
Superhost
Villa in Lilliano
Panoramic villa with pool and airco by Vacavilla
5 bedrooms, 6 beds, 5 bathrooms
12–19 Sept
Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
2 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
4.96 out of 5 average rating, 242 reviews
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
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
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
3 bedrooms, 4 beds, 2.5 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds, 5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Farm stay in Barberino Val d'Elsa
Apartment in a farmhouse in Chianti
4 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 15 reviews
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
Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
New place to stay