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

Top guest favourite
Barn in Castellina in Chianti
Cipressini 2 - pool and amazing views
1 bedroom, 2 beds, 1 private bathroom
17–22 Nov
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5.0 out of 5 average rating, 64 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 18 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, 55 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
5 bedrooms, 5 double beds, 5 bathrooms
22–29 Aug
5.0 out of 5 average rating, 32 reviews
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, 30 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
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
Holiday home in Barberino Tavarnelle
Le Querciole di Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
18–23 Aug
New place to stay
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
3 bedrooms, 3 beds, 2.5 bathrooms
29 Oct – 3 Nov
4.97 out of 5 average rating, 78 reviews
Guest favourite
Flat in Montespertoli
La Casa di Madina – Flo Apartments
3 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 37 reviews
Superhost
Home in Greve in Chianti
Villa with a swimming pool in the heart of Chianti | Florence
3 bedrooms, 3 double beds, 3 bathrooms
27 Aug – 1 Sept
New place to stay
Guest favourite
Room in Castellina in Chianti
Mariani Bed & Breakfast, Double Room 2
1 double bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds, 3 bathrooms
18–23 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 13 reviews
Flat in Certaldo
La Casa di Mario: Apartment near San Gimignano
3 bedrooms, 3 double beds, 1.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Farm stay in Sovicille
Tuscan Villa: Pool, Hot Tub, 4bd, A/C, Wi-Fi, Siena
4 bedrooms, 8 beds, 7.5 bathrooms
21–26 Oct
5.0 out of 5 average rating, 5 reviews