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

Guest favourite
Apartment in Castellina in Chianti
Farmhouse with pool Godenano Di Mezzo
2 bedrooms, 3 beds, 2 private bathrooms
29 Sept – 4 Oct, Individual host
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4.83 out of 5 average rating, 29 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
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
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Castellina in Chianti
Casa Mirella in Chianti
Individual host
26–31 Oct
4.95 out of 5 average rating, 56 reviews
Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
17–22 Oct
5.0 out of 5 average rating, 38 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
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
19–24 Sept
5.0 out of 5 average rating, 10 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, 85 reviews
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
17–22 Sept
Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
31 Oct – 7 Nov
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Barberino Tavarnelle
Podere Le Casette Garden
Business host
11–16 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
10–15 Sept
New place to stay
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
14–19 Oct
5.0 out of 5 average rating, 3 reviews
Guest favourite
Farm stay in Poggibonsi
Holiday home Poggio al olive trees
Business host
16–21 Oct
5.0 out of 5 average rating, 32 reviews
Cottage in Castellina in Chianti
Cottage with a view on Chianti hills
Individual host
19–26 Sept
4.69 out of 5 average rating, 16 reviews
Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
10–15 Sept
5.0 out of 5 average rating, 3 reviews