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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
2–7 Nov, Individual host
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5.0 out of 5 average rating, 98 reviews
Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
17–22 Sept
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
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
Home in Poggibonsi
Relax in Chianti countryside
Individual host
17–22 Oct
5.0 out of 5 average rating, 38 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
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
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 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
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
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
Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
14–19 Sept
5.0 out of 5 average rating, 3 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
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
Individual host
1–6 Oct
5.0 out of 5 average rating, 12 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
Individual host
19–24 Sept
4.9 out of 5 average rating, 30 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
Guest favourite
Villa in San Casciano In Val di Pesa
Archipettoli - Exclusive villa 360 view AC WIFI
Individual host
19–26 Sept
5.0 out of 5 average rating, 13 reviews