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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
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 19 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
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
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
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
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
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
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
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 81 reviews
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
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, 37 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
Guest favourite
Flat in Castellina in Chianti
Two-bedroom apartment
2 bedrooms, 1 bathroom
17–22 Oct
4.8 out of 5 average rating, 10 reviews
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
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
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, 26 reviews
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 12 reviews
Home in Tregole
Romantic villa in the Chianti Classico
8 bedrooms, 9 beds, 8 bathrooms
12–17 Sept