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

Guest favourite
Apartment in Castellina in Chianti
House in agritourism with pool Godenano di Mezzo
1 bedroom, 2 beds, 1 private bathroom
4–9 Oct, Individual host
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4.89 out of 5 average rating, 97 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
27 Oct – 1 Nov
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Barn in Castellina in Chianti
Cipressini 1 - Swimming pool and stunning view
Individual host
2–7 Nov
5.0 out of 5 average rating, 98 reviews
Top guest favourite
Flat in Quercegrossa
Tuscany jem: The Chianti Farmer's House
Individual host
29 Oct – 3 Nov
4.98 out of 5 average rating, 87 reviews
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
Business host
15–22 Oct
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Farm stay in Castellina in Chianti
1st floor apartment with shared pool - 4 pax
Business host
27 Oct – 1 Nov
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Castellina in Chianti
Two-bedroom apartment
Business host
17–22 Oct
4.8 out of 5 average rating, 10 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Home in Tregole
Romantic villa in the Chianti Classico
Business host
12–17 Oct
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
Business host
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
17–22 Sept
Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
24–29 Sept
4.96 out of 5 average rating, 245 reviews
Home in Castellina in Chianti
3 bedroom stone house on olive grove
Individual host
23–28 Sept
5.0 out of 5 average rating, 3 reviews
Home in Fonterutoli
Private house overlooking Siena
Individual host
2–7 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Cottage in Castellina in Chianti
Cottage with a view on Chianti hills
Individual host
3–10 Oct
4.69 out of 5 average rating, 16 reviews