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

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Top guest favourite
Barn in Castellina in Chianti
Cipressini 2 - pool and amazing views
1 bedroom, 2 beds, 1 private bathroom
17–22 Nov, Individual host
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5.0 out of 5 average rating, 67 reviews
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Holiday home in Barberino Tavarnelle
Le Querciole by Mauro Corsi
Individual host
17–22 Sept
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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
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Top guest favourite
Home in Castellina in Chianti
Apartment with stunning view on the vineyards
Business host
20–25 Sept
4.97 out of 5 average rating, 33 reviews
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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
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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
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Top guest favourite
Home in Poggibonsi
Relax in Chianti countryside
Individual host
17–22 Oct
5.0 out of 5 average rating, 38 reviews
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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
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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
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Villa in Greve in Chianti
Villa Le Pozzere
Business host
23–29 Sept
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Figline e Incisa Valdarno
Villa among our vineyards on the outskirts of Chianti
Business host
16–21 Sept
New place to stay
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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
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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
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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
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Superhost
Home in Greve in Chianti
Villa with swimming pool in the heart of Chianti | Florence
Individual host
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Poggibonsi
Wonderful villa for 6 with heatable swimming pool
Individual host
17–24 Oct
5.0 out of 5 average rating, 19 reviews
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Flat in Poggibonsi
Refined Comfort Apartment Villa in Vineyard for 7
Business host
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 reviews