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

Top guest favourite
Cottage in Castellina in Chianti
Cappero Cottage - Masseto In Chianti
2 bedrooms, 3 beds, 2 private bathrooms
23–28 Aug
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4.97 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
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
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
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, 67 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 San Gusmè
Beautiful medieval village!!!
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.99 out of 5 average rating, 467 reviews
Top guest favourite
Room in Lastra a Signa
Sposa Mea
1 bed, 1 bathroom
1–6 Mar
5.0 out of 5 average rating, 74 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
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Barberino Tavarnelle
Authentic Tuscany Experience in our Country House
1 bedroom, 2 beds, 1 bathroom
20–25 Nov
5.0 out of 5 average rating, 83 reviews
Home in Poggibonsi
Le Casacce Farmhouse
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in San Casciano In Val di Pesa
Independent loft in the heart of Chianti
2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 64 reviews
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
16–21 Oct
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 25 reviews
Superhost
Tiny home in Reggello
Idromassaggio Privato • Terrazza con Vista
1 bedroom, 1 double bed, 1 bathroom
4–9 Sept
New place to stay
Guest favourite
Apartment in San Gimignano
Casolare apartment with pool “Casa Monti”
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Bagno A Ripoli
"Antica Stalla" apartment
1 bedroom, 2 beds, 1 bathroom
14–19 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Loro Ciuffenna
Farmhouse apartment
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 14 reviews