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

Ranch in Castellina in Chianti
Lovely Stone Attic • Casa Valeriana
1 bedroom, 2 beds, 1 private bathroom
11–16 Sept
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4.67 out of 5 average rating, 3 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
4 bedrooms, 3 double beds, 4 bathrooms
3–8 Sept
Top guest favourite
Villa in Noce
Villa in Toscana con piscina privata panoramica
2 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 35 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
Home in Poggibonsi
Relax in Chianti countryside
3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
3 bedrooms, 4 beds, 2.5 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
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
25–30 Oct
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
3 bedrooms, 3 beds, 3.5 bathrooms
31 Oct – 7 Nov
5.0 out of 5 average rating, 18 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, 84 reviews
Top guest favourite
Home in Poggibonsi
Il Greppo rustic charm Tuscan views & Hot Tub
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Siena
Terrace on the walls of Siena - Casa Laura
2 bedrooms, 2 beds, 2 bathrooms
30 Nov – 5 Dec
5.0 out of 5 average rating, 104 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
2 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Flat in Barberino Tavarnelle
Podere Le Casette Garden
2 bedrooms, 2 double beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
4 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Farm stay in Poggibonsi
Holiday home Poggio al olive trees
2 bedrooms, 4 beds, 3 bathrooms
16–21 Oct
5.0 out of 5 average rating, 32 reviews