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

Top guest favourite
Home in Castellina in Chianti
Private Chianti Cottage, Garden & Vineyard Views
2 bedrooms, 2 beds, 2 private bathrooms
8–13 Oct
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4.99 out of 5 average rating, 134 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds
29 Oct – 3 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
25–30 Oct
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
2 bedrooms, 3 beds
8–13 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds
25–30 Oct
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
5 bedrooms, 5 king beds
26–31 Oct
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
2 bedrooms, 3 beds
26–31 Oct
4.99 out of 5 average rating, 466 reviews
Guest favourite
Home in Monteriggioni
The Barn Detached house surrounded by greenery
1 bedroom, 2 beds
1–6 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 3 beds
7–12 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Farm stay in Impruneta
"Nocino Apartment" - Farmhouse - Chianti
1 bedroom, 1 double bed
19–24 Aug
5.0 out of 5 average rating, 124 reviews
Top guest favourite
Room in Lastra a Signa
Sposa Mea
1 bed
1–6 Mar
5.0 out of 5 average rating, 71 reviews
Guest favourite
Apartment in San Gimignano
Casolare apartment with pool “Casa Monti”
3 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 10 reviews
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds
15–20 Aug
New place to stay
Top guest favourite
Home in Barberino Tavarnelle
Breathtaking Views in Our Chianti Country House
1 bedroom, 2 beds
20–25 Nov
5.0 out of 5 average rating, 82 reviews
Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
5 bedrooms, 3 single beds
15–22 Oct
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
2 bedrooms, 3 beds
10–15 Oct
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds
19–24 Oct
5.0 out of 5 average rating, 52 reviews