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

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Top guest favourite
Home in Castellina in Chianti
Private Chianti Cottage, Garden & Vineyard Views
2 bedrooms, 2 beds, 2 private bathrooms
24–29 Oct, Business host
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4.99 out of 5 average rating, 137 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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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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Superhost
Home in Castellina in Chianti
Cinderella Chianti - House
Individual host
29 Sept – 4 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Fonterutoli
Private house overlooking Siena
Individual host
2–7 Nov
5.0 out of 5 average rating, 3 reviews
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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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Home in Castellina in Chianti
3 bedroom stone house on olive grove
Individual host
23–28 Sept
5.0 out of 5 average rating, 3 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 Poggibonsi
Casal De' Matti - Margot House
Business host
16–21 Oct
4.98 out of 5 average rating, 47 reviews
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Superhost
Villa in Lilliano
Panoramic villa with pool and airco by Vacavilla
Business host
21–28 Oct
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Home in Castellina in Chianti
Cignanbianco - Sunrise and Sunset by Interhome
Business host
15–22 Oct
4.75 out of 5 average rating, 4 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
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 69 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, 142 reviews
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Home in Tregole
Romantic villa in the Chianti Classico
Business host
12–17 Oct
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Top guest favourite
Villa in Barberino Tavarnelle
Valluccia 51
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 50 reviews
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Villa in Madonna di Pietracupa
Villa sonia - luxury villa rental in madonna di pi
Business host
17–24 Oct
5.0 out of 5 average rating, 3 reviews
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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
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
New place to stay