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Search results; Over 1,000 homes in Castell'In Villa

Guest favourite
Villa in Castell'In Villa
Villa marielena chianti farmhouse with hot tub - v
4 bedrooms, 4 beds, 4 private bathrooms
7–12 Sept
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5.0 out of 5 average rating, 10 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, 470 reviews
Top guest favourite
Home in Villa A Sesta
Raffaella's House in Chianti
2 bedrooms, 3 beds, 1 bathroom
28 Oct – 2 Nov
4.99 out of 5 average rating, 479 reviews
Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
2 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
2 bedrooms, 3 beds, 2 bathrooms
7–12 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Loft in Siena
Siena Country Loft Hideway
1 bedroom, 1 bed, 2 bathrooms
12–17 Oct
4.95 out of 5 average rating, 254 reviews
Guest favourite
Flat in San Gusmè
La Dimora del Luca
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.98 out of 5 average rating, 169 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Room in Gaiole in Chianti
Argentina. Welcome to our small village, L...
2 beds, 1 bathroom
17–22 Oct
4.95 out of 5 average rating, 21 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
Superhost
Home in Gaiole in Chianti
Villa Melina - new life for the barn
1 bedroom, 1 bed, 1 bathroom
10–15 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
3 bedrooms, 3 double beds, 3.5 bathrooms
6–11 Sept
4.99 out of 5 average rating, 113 reviews
Superhost
Flat in Siena
Tiziana: Charming Stay on Winery Estate
3 bedrooms, 4 beds, 3 bathrooms
6–11 Sept
Top guest favourite
Holiday home in Siena
New! Luxury Apartment in Historic Centre of Siena
3 bedrooms, 4 beds, 2 bathrooms
23–28 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Siena
[NEW!] Renovated, just a stone's throw from the center!
2 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 19 reviews
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
4 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Gaiole in Chianti
Galendino
2 bedrooms, 2 beds, 2 bathrooms
19–26 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Apartment in Siena
Luxury Penthouse with a View of Piazza del Campo
3 bedrooms, 3 beds, 4 bathrooms
25–30 Oct
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Moncioni
Private Tuscan hilltop farmhouse with pool
5 bedrooms, 7 beds, 4 bathrooms
6–11 Sept
4.9 out of 5 average rating, 30 reviews