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Search results; Over 1,000 homes in Castelnuovo Berardenga

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Guest favourite
Holiday home in Castelnuovo Berardenga
PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶
5 bedrooms, 10 beds, 5 private bathrooms
26 Sept – 1 Oct, Individual host
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4.91 out of 5 average rating, 100 reviews
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Guest favourite
Room in Castelnuovo Berardenga
Private room in Bed and Breakfast Casa Cernano,...
Individual host
5–10 Oct
5.0 out of 5 average rating, 14 reviews
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Superhost
Flat in Bossi
Villino Ersilia Music, the charm of Chianti
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 4 reviews
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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
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Top guest favourite
Flat in San Gusmè
Beautiful medieval village!!!
Individual host
30 Oct – 4 Nov
4.99 out of 5 average rating, 472 reviews
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Superhost
Home in Castelnuovo Berardenga
Camere in Bed and Breakfast Casa Cernano
Individual host
16–21 Sept
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Guest favourite
Home in Rapolano Terme
The Golden Stone
Individual host
11–16 Oct
4.92 out of 5 average rating, 12 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Guest favourite
Apartment in Castelnuovo Berardenga
The Family Home between Siena, Chianti and Crete
Individual host
16–21 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 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
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Top guest favourite
Villa in Pergine Valdarno
La Vignaccia (Farmhouse) - villa w/private pool
Business host
26 Sept – 3 Oct
4.96 out of 5 average rating, 102 reviews
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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
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
Individual host
16–21 Sept
4.98 out of 5 average rating, 49 reviews
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Top guest favourite
Farm stay in Castelnuovo Berardenga
Bed and Breakfast Casa Cernano
Individual host
16–21 Sept
4.92 out of 5 average rating, 215 reviews
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Guest favourite
Apartment in Castelnuovo Berardenga
Large apartment in the heart of Chianti
Individual host
19–24 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
Business host
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Holiday home in Rosennano
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
Business host
22–27 Sept
4.99 out of 5 average rating, 78 reviews