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

Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
1 bedroom, 3 beds, 1 private bathroom
29 Oct – 3 Nov
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5.0 out of 5 average rating, 96 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
4.94 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 1 bathroom
25–30 Jul
Top guest favourite
Loft in Castellina in Chianti
Palazzo Bianciardi - Penthouse
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Aug
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
4.97 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
Top guest favourite
Apartment in Fonterutoli
Borgo di Fonterutoli: among vineyards and relaxation
4.95 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Flat in Castellina in Chianti
Apartment in the heart of Chianti
2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
4.98 out of 5 average rating, 45 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Oct
Top guest favourite
Flat in Poggibonsi
Villa Mocarello "IL LECCIO"
5.0 out of 5 average rating, 127 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Castellina in Chianti
Visit Chianti, Florence, Siena, San Gimignano
4.97 out of 5 average rating, 136 reviews, 2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
4.97 out of 5 average rating, 73 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Oct
Guest favourite
Flat in Castellina in Chianti
Cogno Mill - Il Ritrecine
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Aug
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
Top guest favourite
Farm stay in Greve in Chianti
Old hayloft on the Chianti hills
4.99 out of 5 average rating, 475 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Dec
Superhost
Home in Gaiole in Chianti
Fienile House
New place to stay, 2 bedrooms, 2 beds, 2.5 bathrooms
21–26 Aug
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Home in Poggibonsi
Casa Iris (with jacuzzi) - Close to San Gimignano
4.98 out of 5 average rating, 66 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Nov
Top guest favourite
Flat in Barberino Val d'Elsa
Apartment in Chianti at Mulino dell'Argenna
4.99 out of 5 average rating, 146 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Sept
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
Guest favourite
Room in Castellina in Chianti
Mariani Bed & Breakfast, Double Room 2
5.0 out of 5 average rating, 12 reviews, 1 double bed, 1 bathroom
7–12 Aug